diff --git a/CHANGELOG.md b/CHANGELOG.md
index e9ac7191..6c74144e 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -2,8 +2,16 @@
 
 **TBD (TBD):**
 
+**0.13.0 (2022-xx-xx):**
+
+**Features**:
+
+- Add IPv6 support to the prefix assigned to namespaces
+
 **Changes**:
 
+- `ip_prefix` is now superseded by `ip_prefixes` in the configuration [#208](https://github.com/juanfont/headscale/pull/208)
+
 **0.12.4 (2022-01-29):**
 
 **Changes**:
diff --git a/Dockerfile b/Dockerfile
index d5fe3421..050439b5 100644
--- a/Dockerfile
+++ b/Dockerfile
@@ -1,5 +1,5 @@
 # Builder image
-FROM golang:1.17.6-bullseye AS build
+FROM docker.io/golang:1.17.1-bullseye AS build
 ENV GOPATH /go
 WORKDIR /go/src/headscale
 
diff --git a/Dockerfile.alpine b/Dockerfile.alpine
index 8185dbe4..a75bbfea 100644
--- a/Dockerfile.alpine
+++ b/Dockerfile.alpine
@@ -1,5 +1,5 @@
 # Builder image
-FROM golang:1.17.6-alpine AS build
+FROM docker.io/golang:1.17.1-alpine AS build
 ENV GOPATH /go
 WORKDIR /go/src/headscale
 
@@ -14,7 +14,7 @@ RUN strip /go/bin/headscale
 RUN test -e /go/bin/headscale
 
 # Production image
-FROM alpine:latest
+FROM docker.io/alpine:latest
 
 COPY --from=build /go/bin/headscale /bin/headscale
 ENV TZ UTC
diff --git a/Dockerfile.debug b/Dockerfile.debug
index 320b5c93..b81ee67e 100644
--- a/Dockerfile.debug
+++ b/Dockerfile.debug
@@ -1,5 +1,5 @@
 # Builder image
-FROM golang:1.17.1-bullseye AS build
+FROM docker.io/golang:1.17.1-bullseye AS build
 ENV GOPATH /go
 WORKDIR /go/src/headscale
 
diff --git a/Dockerfile.tailscale b/Dockerfile.tailscale
index df8cdcb1..f96c6b9c 100644
--- a/Dockerfile.tailscale
+++ b/Dockerfile.tailscale
@@ -7,5 +7,5 @@ RUN apt-get update \
     && curl -fsSL https://pkgs.tailscale.com/stable/ubuntu/focal.gpg | apt-key add - \
     && curl -fsSL https://pkgs.tailscale.com/stable/ubuntu/focal.list | tee /etc/apt/sources.list.d/tailscale.list \
     && apt-get update \
-    && apt-get install -y tailscale=${TAILSCALE_VERSION} \
+    && apt-get install -y tailscale=${TAILSCALE_VERSION} dnsutils \
     && rm -rf /var/lib/apt/lists/*
diff --git a/Makefile b/Makefile
index 6b4c02ff..69935bc0 100644
--- a/Makefile
+++ b/Makefile
@@ -18,7 +18,7 @@ test:
 	@go test -coverprofile=coverage.out ./...
 
 test_integration:
-	go test -tags integration -timeout 30m ./...
+	go test -tags integration -timeout 30m -count=1 ./...
 
 test_integration_cli:
 	go test -tags integration -v integration_cli_test.go integration_common_test.go
diff --git a/acls.go b/acls.go
index 1d54b26d..326625b9 100644
--- a/acls.go
+++ b/acls.go
@@ -188,7 +188,7 @@ func (h *Headscale) expandAlias(alias string) ([]string, error) {
 				return nil, errInvalidNamespace
 			}
 			for _, node := range nodes {
-				ips = append(ips, node.IPAddress)
+				ips = append(ips, node.IPAddresses.ToStringSlice()...)
 			}
 		}
 
@@ -222,7 +222,7 @@ func (h *Headscale) expandAlias(alias string) ([]string, error) {
 				// FIXME: Check TagOwners allows this
 				for _, t := range hostinfo.RequestTags {
 					if alias[4:] == t {
-						ips = append(ips, machine.IPAddress)
+						ips = append(ips, machine.IPAddresses.ToStringSlice()...)
 
 						break
 					}
@@ -241,7 +241,7 @@ func (h *Headscale) expandAlias(alias string) ([]string, error) {
 		}
 		ips := []string{}
 		for _, n := range nodes {
-			ips = append(ips, n.IPAddress)
+			ips = append(ips, n.IPAddresses.ToStringSlice()...)
 		}
 
 		return ips, nil
diff --git a/acls_test.go b/acls_test.go
index 629ce1da..c35f4f84 100644
--- a/acls_test.go
+++ b/acls_test.go
@@ -61,9 +61,9 @@ func (s *Suite) TestPortRange(c *check.C) {
 	c.Assert(rules, check.NotNil)
 
 	c.Assert(rules, check.HasLen, 1)
-	c.Assert((rules)[0].DstPorts, check.HasLen, 1)
-	c.Assert((rules)[0].DstPorts[0].Ports.First, check.Equals, uint16(5400))
-	c.Assert((rules)[0].DstPorts[0].Ports.Last, check.Equals, uint16(5500))
+	c.Assert(rules[0].DstPorts, check.HasLen, 1)
+	c.Assert(rules[0].DstPorts[0].Ports.First, check.Equals, uint16(5400))
+	c.Assert(rules[0].DstPorts[0].Ports.Last, check.Equals, uint16(5500))
 }
 
 func (s *Suite) TestPortWildcard(c *check.C) {
@@ -75,11 +75,11 @@ func (s *Suite) TestPortWildcard(c *check.C) {
 	c.Assert(rules, check.NotNil)
 
 	c.Assert(rules, check.HasLen, 1)
-	c.Assert((rules)[0].DstPorts, check.HasLen, 1)
-	c.Assert((rules)[0].DstPorts[0].Ports.First, check.Equals, uint16(0))
-	c.Assert((rules)[0].DstPorts[0].Ports.Last, check.Equals, uint16(65535))
-	c.Assert((rules)[0].SrcIPs, check.HasLen, 1)
-	c.Assert((rules)[0].SrcIPs[0], check.Equals, "*")
+	c.Assert(rules[0].DstPorts, check.HasLen, 1)
+	c.Assert(rules[0].DstPorts[0].Ports.First, check.Equals, uint16(0))
+	c.Assert(rules[0].DstPorts[0].Ports.Last, check.Equals, uint16(65535))
+	c.Assert(rules[0].SrcIPs, check.HasLen, 1)
+	c.Assert(rules[0].SrcIPs[0], check.Equals, "*")
 }
 
 func (s *Suite) TestPortNamespace(c *check.C) {
@@ -91,7 +91,7 @@ func (s *Suite) TestPortNamespace(c *check.C) {
 
 	_, err = app.GetMachine("testnamespace", "testmachine")
 	c.Assert(err, check.NotNil)
-	ip, _ := app.getAvailableIP()
+	ips, _ := app.getAvailableIPs()
 	machine := Machine{
 		ID:             0,
 		MachineKey:     "foo",
@@ -101,7 +101,7 @@ func (s *Suite) TestPortNamespace(c *check.C) {
 		NamespaceID:    namespace.ID,
 		Registered:     true,
 		RegisterMethod: RegisterMethodAuthKey,
-		IPAddress:      ip.String(),
+		IPAddresses:    ips,
 		AuthKeyID:      uint(pak.ID),
 	}
 	app.db.Save(&machine)
@@ -116,12 +116,13 @@ func (s *Suite) TestPortNamespace(c *check.C) {
 	c.Assert(rules, check.NotNil)
 
 	c.Assert(rules, check.HasLen, 1)
-	c.Assert((rules)[0].DstPorts, check.HasLen, 1)
-	c.Assert((rules)[0].DstPorts[0].Ports.First, check.Equals, uint16(0))
-	c.Assert((rules)[0].DstPorts[0].Ports.Last, check.Equals, uint16(65535))
-	c.Assert((rules)[0].SrcIPs, check.HasLen, 1)
-	c.Assert((rules)[0].SrcIPs[0], check.Not(check.Equals), "not an ip")
-	c.Assert((rules)[0].SrcIPs[0], check.Equals, ip.String())
+	c.Assert(rules[0].DstPorts, check.HasLen, 1)
+	c.Assert(rules[0].DstPorts[0].Ports.First, check.Equals, uint16(0))
+	c.Assert(rules[0].DstPorts[0].Ports.Last, check.Equals, uint16(65535))
+	c.Assert(rules[0].SrcIPs, check.HasLen, 1)
+	c.Assert(rules[0].SrcIPs[0], check.Not(check.Equals), "not an ip")
+	c.Assert(len(ips), check.Equals, 1)
+	c.Assert(rules[0].SrcIPs[0], check.Equals, ips[0].String())
 }
 
 func (s *Suite) TestPortGroup(c *check.C) {
@@ -133,7 +134,7 @@ func (s *Suite) TestPortGroup(c *check.C) {
 
 	_, err = app.GetMachine("testnamespace", "testmachine")
 	c.Assert(err, check.NotNil)
-	ip, _ := app.getAvailableIP()
+	ips, _ := app.getAvailableIPs()
 	machine := Machine{
 		ID:             0,
 		MachineKey:     "foo",
@@ -143,7 +144,7 @@ func (s *Suite) TestPortGroup(c *check.C) {
 		NamespaceID:    namespace.ID,
 		Registered:     true,
 		RegisterMethod: RegisterMethodAuthKey,
-		IPAddress:      ip.String(),
+		IPAddresses:    ips,
 		AuthKeyID:      uint(pak.ID),
 	}
 	app.db.Save(&machine)
@@ -156,10 +157,11 @@ func (s *Suite) TestPortGroup(c *check.C) {
 	c.Assert(rules, check.NotNil)
 
 	c.Assert(rules, check.HasLen, 1)
-	c.Assert((rules)[0].DstPorts, check.HasLen, 1)
-	c.Assert((rules)[0].DstPorts[0].Ports.First, check.Equals, uint16(0))
-	c.Assert((rules)[0].DstPorts[0].Ports.Last, check.Equals, uint16(65535))
-	c.Assert((rules)[0].SrcIPs, check.HasLen, 1)
-	c.Assert((rules)[0].SrcIPs[0], check.Not(check.Equals), "not an ip")
-	c.Assert((rules)[0].SrcIPs[0], check.Equals, ip.String())
+	c.Assert(rules[0].DstPorts, check.HasLen, 1)
+	c.Assert(rules[0].DstPorts[0].Ports.First, check.Equals, uint16(0))
+	c.Assert(rules[0].DstPorts[0].Ports.Last, check.Equals, uint16(65535))
+	c.Assert(rules[0].SrcIPs, check.HasLen, 1)
+	c.Assert(rules[0].SrcIPs[0], check.Not(check.Equals), "not an ip")
+	c.Assert(len(ips), check.Equals, 1)
+	c.Assert(rules[0].SrcIPs[0], check.Equals, ips[0].String())
 }
diff --git a/api.go b/api.go
index d3bd5726..020ded01 100644
--- a/api.go
+++ b/api.go
@@ -497,6 +497,7 @@ func (h *Headscale) handleMachineRegistrationNew(
 	ctx.Data(http.StatusOK, "application/json; charset=utf-8", respBody)
 }
 
+// TODO: check if any locks are needed around IP allocation.
 func (h *Headscale) handleAuthKey(
 	ctx *gin.Context,
 	machineKey key.MachinePublic,
@@ -554,14 +555,14 @@ func (h *Headscale) handleAuthKey(
 		log.Debug().
 			Str("func", "handleAuthKey").
 			Str("machine", machine.Name).
-			Msg("Authentication key was valid, proceeding to acquire an IP address")
-		ip, err := h.getAvailableIP()
+			Msg("Authentication key was valid, proceeding to acquire IP addresses")
+		ips, err := h.getAvailableIPs()
 		if err != nil {
 			log.Error().
 				Caller().
 				Str("func", "handleAuthKey").
 				Str("machine", machine.Name).
-				Msg("Failed to find an available IP")
+				Msg("Failed to find an available IP address")
 			machineRegistrations.WithLabelValues("new", "authkey", "error", machine.Namespace.Name).
 				Inc()
 
@@ -570,12 +571,12 @@ func (h *Headscale) handleAuthKey(
 		log.Info().
 			Str("func", "handleAuthKey").
 			Str("machine", machine.Name).
-			Str("ip", ip.String()).
-			Msgf("Assigning %s to %s", ip, machine.Name)
+			Str("ips", strings.Join(ips.ToStringSlice(), ",")).
+			Msgf("Assigning %s to %s", strings.Join(ips.ToStringSlice(), ","), machine.Name)
 
 		machine.Expiry = &registerRequest.Expiry
 		machine.AuthKeyID = uint(pak.ID)
-		machine.IPAddress = ip.String()
+		machine.IPAddresses = ips
 		machine.NamespaceID = pak.NamespaceID
 
 		machine.NodeKey = NodePublicKeyStripPrefix(registerRequest.NodeKey)
@@ -610,6 +611,6 @@ func (h *Headscale) handleAuthKey(
 	log.Info().
 		Str("func", "handleAuthKey").
 		Str("machine", machine.Name).
-		Str("ip", machine.IPAddress).
+		Str("ips", strings.Join(machine.IPAddresses.ToStringSlice(), ", ")).
 		Msg("Successfully authenticated via AuthKey")
 }
diff --git a/app.go b/app.go
index 5cc1b5c9..bc7491ce 100644
--- a/app.go
+++ b/app.go
@@ -69,7 +69,7 @@ type Config struct {
 	ServerURL                      string
 	Addr                           string
 	EphemeralNodeInactivityTimeout time.Duration
-	IPPrefix                       netaddr.IPPrefix
+	IPPrefixes                     []netaddr.IPPrefix
 	PrivateKeyPath                 string
 	BaseDomain                     string
 
@@ -199,9 +199,7 @@ func NewHeadscale(cfg Config) (*Headscale, error) {
 	}
 
 	if app.cfg.DNSConfig != nil && app.cfg.DNSConfig.Proxied { // if MagicDNS
-		magicDNSDomains := generateMagicDNSRootDomains(
-			app.cfg.IPPrefix,
-		)
+		magicDNSDomains := generateMagicDNSRootDomains(app.cfg.IPPrefixes)
 		// we might have routes already from Split DNS
 		if app.cfg.DNSConfig.Routes == nil {
 			app.cfg.DNSConfig.Routes = make(map[string][]dnstype.Resolver)
diff --git a/app_test.go b/app_test.go
index bff13933..02fdce8b 100644
--- a/app_test.go
+++ b/app_test.go
@@ -41,7 +41,9 @@ func (s *Suite) ResetDB(c *check.C) {
 		c.Fatal(err)
 	}
 	cfg := Config{
-		IPPrefix: netaddr.MustParseIPPrefix("10.27.0.0/23"),
+		IPPrefixes: []netaddr.IPPrefix{
+			netaddr.MustParseIPPrefix("10.27.0.0/23"),
+		},
 	}
 
 	app = Headscale{
diff --git a/cli_test.go b/cli_test.go
index ef7e2993..71f2bea5 100644
--- a/cli_test.go
+++ b/cli_test.go
@@ -4,6 +4,7 @@ import (
 	"time"
 
 	"gopkg.in/check.v1"
+	"inet.af/netaddr"
 )
 
 func (s *Suite) TestRegisterMachine(c *check.C) {
@@ -19,16 +20,17 @@ func (s *Suite) TestRegisterMachine(c *check.C) {
 		DiscoKey:    "faa",
 		Name:        "testmachine",
 		NamespaceID: namespace.ID,
-		IPAddress:   "10.0.0.1",
+		IPAddresses: []netaddr.IP{netaddr.MustParseIP("10.0.0.1")},
 		Expiry:      &now,
 	}
-	app.db.Save(&machine)
+	err = app.db.Save(&machine).Error
+	c.Assert(err, check.IsNil)
 
-	_, err = app.GetMachine("test", "testmachine")
+	_, err = app.GetMachine(namespace.Name, machine.Name)
 	c.Assert(err, check.IsNil)
 
 	machineAfterRegistering, err := app.RegisterMachine(
-		"8ce002a935f8c394e55e78fbbb410576575ff8ec5cfa2e627e4b807f1be15b0e",
+		machine.MachineKey,
 		namespace.Name,
 	)
 	c.Assert(err, check.IsNil)
diff --git a/cmd/headscale/cli/nodes.go b/cmd/headscale/cli/nodes.go
index 26ead6dc..d6b86ee1 100644
--- a/cmd/headscale/cli/nodes.go
+++ b/cmd/headscale/cli/nodes.go
@@ -4,6 +4,7 @@ import (
 	"fmt"
 	"log"
 	"strconv"
+	"strings"
 	"time"
 
 	survey "github.com/AlecAivazis/survey/v2"
@@ -459,7 +460,7 @@ func nodesToPtables(
 			"Name",
 			"NodeKey",
 			"Namespace",
-			"IP address",
+			"IP addresses",
 			"Ephemeral",
 			"Last seen",
 			"Online",
@@ -523,7 +524,7 @@ func nodesToPtables(
 				machine.Name,
 				nodeKey.ShortString(),
 				namespace,
-				machine.IpAddress,
+				strings.Join(machine.IpAddresses, ", "),
 				strconv.FormatBool(ephemeral),
 				lastSeenTime,
 				online,
diff --git a/cmd/headscale/cli/utils.go b/cmd/headscale/cli/utils.go
index c2016271..258acf33 100644
--- a/cmd/headscale/cli/utils.go
+++ b/cmd/headscale/cli/utils.go
@@ -47,8 +47,6 @@ func LoadConfig(path string) error {
 	viper.SetDefault("tls_letsencrypt_cache_dir", "/var/www/.cache")
 	viper.SetDefault("tls_letsencrypt_challenge_type", "HTTP-01")
 
-	viper.SetDefault("ip_prefix", "100.64.0.0/10")
-
 	viper.SetDefault("log_level", "info")
 
 	viper.SetDefault("dns_config", nil)
@@ -228,10 +226,57 @@ func getHeadscaleConfig() headscale.Config {
 	dnsConfig, baseDomain := GetDNSConfig()
 	derpConfig := GetDERPConfig()
 
+	configuredPrefixes := viper.GetStringSlice("ip_prefixes")
+	parsedPrefixes := make([]netaddr.IPPrefix, 0, len(configuredPrefixes)+1)
+
+	legacyPrefixField := viper.GetString("ip_prefix")
+	if len(legacyPrefixField) > 0 {
+		log.
+			Warn().
+			Msgf(
+				"%s, %s",
+				"use of 'ip_prefix' for configuration is deprecated",
+				"please see 'ip_prefixes' in the shipped example.",
+			)
+		legacyPrefix, err := netaddr.ParseIPPrefix(legacyPrefixField)
+		if err != nil {
+			panic(fmt.Errorf("failed to parse ip_prefix: %w", err))
+		}
+		parsedPrefixes = append(parsedPrefixes, legacyPrefix)
+	}
+
+	for i, prefixInConfig := range configuredPrefixes {
+		prefix, err := netaddr.ParseIPPrefix(prefixInConfig)
+		if err != nil {
+			panic(fmt.Errorf("failed to parse ip_prefixes[%d]: %w", i, err))
+		}
+		parsedPrefixes = append(parsedPrefixes, prefix)
+	}
+
+	prefixes := make([]netaddr.IPPrefix, 0, len(parsedPrefixes))
+	{
+		// dedup
+		normalizedPrefixes := make(map[string]int, len(parsedPrefixes))
+		for i, p := range parsedPrefixes {
+			normalized, _ := p.Range().Prefix()
+			normalizedPrefixes[normalized.String()] = i
+		}
+
+		// convert back to list
+		for _, i := range normalizedPrefixes {
+			prefixes = append(prefixes, parsedPrefixes[i])
+		}
+	}
+
+	if len(prefixes) < 1 {
+		prefixes = append(prefixes, netaddr.MustParseIPPrefix("100.64.0.0/10"))
+		log.Warn().Msgf("'ip_prefixes' not configured, falling back to default: %v", prefixes)
+	}
+
 	return headscale.Config{
 		ServerURL:      viper.GetString("server_url"),
 		Addr:           viper.GetString("listen_addr"),
-		IPPrefix:       netaddr.MustParseIPPrefix(viper.GetString("ip_prefix")),
+		IPPrefixes:     prefixes,
 		PrivateKeyPath: absPath(viper.GetString("private_key_path")),
 		BaseDomain:     baseDomain,
 
diff --git a/config-example.yaml b/config-example.yaml
index 3a867a36..940fe57f 100644
--- a/config-example.yaml
+++ b/config-example.yaml
@@ -22,6 +22,13 @@ listen_addr: 0.0.0.0:8080
 # autogenerated if it's missing
 private_key_path: /var/lib/headscale/private.key
 
+# List of IP prefixes to allocate tailaddresses from.
+# Each prefix consists of either an IPv4 or IPv6 address,
+# and the associated prefix length, delimited by a slash.
+ip_prefixes:
+  - fd7a:115c:a1e0::/48
+  - 100.64.0.0/10
+
 # DERP is a relay system that Tailscale uses when a direct
 # connection cannot be established.
 # https://tailscale.com/blog/how-tailscale-works/#encrypted-tcp-relays-derp
diff --git a/dns.go b/dns.go
index af6f989d..df896090 100644
--- a/dns.go
+++ b/dns.go
@@ -14,6 +14,11 @@ const (
 	ByteSize = 8
 )
 
+const (
+	ipv4AddressLength = 32
+	ipv6AddressLength = 128
+)
+
 // generateMagicDNSRootDomains generates a list of DNS entries to be included in `Routes` in `MapResponse`.
 // This list of reverse DNS entries instructs the OS on what subnets and domains the Tailscale embedded DNS
 // server (listening in 100.100.100.100 udp/53) should be used for.
@@ -34,14 +39,28 @@ const (
 
 // From the netmask we can find out the wildcard bits (the bits that are not set in the netmask).
 // This allows us to then calculate the subnets included in the subsequent class block and generate the entries.
-func generateMagicDNSRootDomains(
-	ipPrefix netaddr.IPPrefix,
-) []dnsname.FQDN {
-	// TODO(juanfont): we are not handing out IPv6 addresses yet
-	// and in fact this is Tailscale.com's range (note the fd7a:115c:a1e0: range in the fc00::/7 network)
-	ipv6base := dnsname.FQDN("0.e.1.a.c.5.1.1.a.7.d.f.ip6.arpa.")
-	fqdns := []dnsname.FQDN{ipv6base}
+func generateMagicDNSRootDomains(ipPrefixes []netaddr.IPPrefix) []dnsname.FQDN {
+	fqdns := make([]dnsname.FQDN, 0, len(ipPrefixes))
+	for _, ipPrefix := range ipPrefixes {
+		var generateDNSRoot func(netaddr.IPPrefix) []dnsname.FQDN
+		switch ipPrefix.IP().BitLen() {
+		case ipv4AddressLength:
+			generateDNSRoot = generateIPv4DNSRootDomain
 
+		case ipv6AddressLength:
+			generateDNSRoot = generateIPv6DNSRootDomain
+
+		default:
+			panic(fmt.Sprintf("unsupported IP version with address length %d", ipPrefix.IP().BitLen()))
+		}
+
+		fqdns = append(fqdns, generateDNSRoot(ipPrefix)...)
+	}
+
+	return fqdns
+}
+
+func generateIPv4DNSRootDomain(ipPrefix netaddr.IPPrefix) []dnsname.FQDN {
 	// Conversion to the std lib net.IPnet, a bit easier to operate
 	netRange := ipPrefix.IPNet()
 	maskBits, _ := netRange.Mask.Size()
@@ -65,6 +84,7 @@ func generateMagicDNSRootDomains(
 	rdnsSlice = append(rdnsSlice, "in-addr.arpa.")
 	rdnsBase := strings.Join(rdnsSlice, ".")
 
+	fqdns := make([]dnsname.FQDN, 0, max-min+1)
 	for i := min; i <= max; i++ {
 		fqdn, err := dnsname.ToFQDN(fmt.Sprintf("%d.%s", i, rdnsBase))
 		if err != nil {
@@ -76,6 +96,54 @@ func generateMagicDNSRootDomains(
 	return fqdns
 }
 
+func generateIPv6DNSRootDomain(ipPrefix netaddr.IPPrefix) []dnsname.FQDN {
+	const nibbleLen = 4
+
+	maskBits, _ := ipPrefix.IPNet().Mask.Size()
+	expanded := ipPrefix.IP().StringExpanded()
+	nibbleStr := strings.Map(func(r rune) rune {
+		if r == ':' {
+			return -1
+		}
+
+		return r
+	}, expanded)
+
+	// TODO?: that does not look the most efficient implementation,
+	// but the inputs are not so long as to cause problems,
+	// and from what I can see, the generateMagicDNSRootDomains
+	// function is called only once over the lifetime of a server process.
+	prefixConstantParts := []string{}
+	for i := 0; i < maskBits/nibbleLen; i++ {
+		prefixConstantParts = append([]string{string(nibbleStr[i])}, prefixConstantParts...)
+	}
+
+	makeDomain := func(variablePrefix ...string) (dnsname.FQDN, error) {
+		prefix := strings.Join(append(variablePrefix, prefixConstantParts...), ".")
+
+		return dnsname.ToFQDN(fmt.Sprintf("%s.ip6.arpa", prefix))
+	}
+
+	var fqdns []dnsname.FQDN
+	if maskBits%4 == 0 {
+		dom, _ := makeDomain()
+		fqdns = append(fqdns, dom)
+	} else {
+		domCount := 1 << (maskBits % nibbleLen)
+		fqdns = make([]dnsname.FQDN, 0, domCount)
+		for i := 0; i < domCount; i++ {
+			varNibble := fmt.Sprintf("%x", i)
+			dom, err := makeDomain(varNibble)
+			if err != nil {
+				continue
+			}
+			fqdns = append(fqdns, dom)
+		}
+	}
+
+	return fqdns
+}
+
 func getMapResponseDNSConfig(
 	dnsConfigOrig *tailcfg.DNSConfig,
 	baseDomain string,
diff --git a/dns_test.go b/dns_test.go
index 92f7476f..f8f7fb96 100644
--- a/dns_test.go
+++ b/dns_test.go
@@ -10,8 +10,10 @@ import (
 )
 
 func (s *Suite) TestMagicDNSRootDomains100(c *check.C) {
-	prefix := netaddr.MustParseIPPrefix("100.64.0.0/10")
-	domains := generateMagicDNSRootDomains(prefix)
+	prefixes := []netaddr.IPPrefix{
+		netaddr.MustParseIPPrefix("100.64.0.0/10"),
+	}
+	domains := generateMagicDNSRootDomains(prefixes)
 
 	found := false
 	for _, domain := range domains {
@@ -45,8 +47,10 @@ func (s *Suite) TestMagicDNSRootDomains100(c *check.C) {
 }
 
 func (s *Suite) TestMagicDNSRootDomains172(c *check.C) {
-	prefix := netaddr.MustParseIPPrefix("172.16.0.0/16")
-	domains := generateMagicDNSRootDomains(prefix)
+	prefixes := []netaddr.IPPrefix{
+		netaddr.MustParseIPPrefix("172.16.0.0/16"),
+	}
+	domains := generateMagicDNSRootDomains(prefixes)
 
 	found := false
 	for _, domain := range domains {
@@ -69,6 +73,40 @@ func (s *Suite) TestMagicDNSRootDomains172(c *check.C) {
 	c.Assert(found, check.Equals, true)
 }
 
+// Happens when netmask is a multiple of 4 bits (sounds likely).
+func (s *Suite) TestMagicDNSRootDomainsIPv6Single(c *check.C) {
+	prefixes := []netaddr.IPPrefix{
+		netaddr.MustParseIPPrefix("fd7a:115c:a1e0::/48"),
+	}
+	domains := generateMagicDNSRootDomains(prefixes)
+
+	c.Assert(len(domains), check.Equals, 1)
+	c.Assert(domains[0].WithTrailingDot(), check.Equals, "0.e.1.a.c.5.1.1.a.7.d.f.ip6.arpa.")
+}
+
+func (s *Suite) TestMagicDNSRootDomainsIPv6SingleMultiple(c *check.C) {
+	prefixes := []netaddr.IPPrefix{
+		netaddr.MustParseIPPrefix("fd7a:115c:a1e0::/50"),
+	}
+	domains := generateMagicDNSRootDomains(prefixes)
+
+	yieldsRoot := func(dom string) bool {
+		for _, candidate := range domains {
+			if candidate.WithTrailingDot() == dom {
+				return true
+			}
+		}
+
+		return false
+	}
+
+	c.Assert(len(domains), check.Equals, 4)
+	c.Assert(yieldsRoot("0.0.e.1.a.c.5.1.1.a.7.d.f.ip6.arpa."), check.Equals, true)
+	c.Assert(yieldsRoot("1.0.e.1.a.c.5.1.1.a.7.d.f.ip6.arpa."), check.Equals, true)
+	c.Assert(yieldsRoot("2.0.e.1.a.c.5.1.1.a.7.d.f.ip6.arpa."), check.Equals, true)
+	c.Assert(yieldsRoot("3.0.e.1.a.c.5.1.1.a.7.d.f.ip6.arpa."), check.Equals, true)
+}
+
 func (s *Suite) TestDNSConfigMapResponseWithMagicDNS(c *check.C) {
 	namespaceShared1, err := app.CreateNamespace("shared1")
 	c.Assert(err, check.IsNil)
@@ -124,7 +162,7 @@ func (s *Suite) TestDNSConfigMapResponseWithMagicDNS(c *check.C) {
 		Namespace:      *namespaceShared1,
 		Registered:     true,
 		RegisterMethod: RegisterMethodAuthKey,
-		IPAddress:      "100.64.0.1",
+		IPAddresses:    []netaddr.IP{netaddr.MustParseIP("100.64.0.1")},
 		AuthKeyID:      uint(preAuthKeyInShared1.ID),
 	}
 	app.db.Save(machineInShared1)
@@ -142,7 +180,7 @@ func (s *Suite) TestDNSConfigMapResponseWithMagicDNS(c *check.C) {
 		Namespace:      *namespaceShared2,
 		Registered:     true,
 		RegisterMethod: RegisterMethodAuthKey,
-		IPAddress:      "100.64.0.2",
+		IPAddresses:    []netaddr.IP{netaddr.MustParseIP("100.64.0.2")},
 		AuthKeyID:      uint(preAuthKeyInShared2.ID),
 	}
 	app.db.Save(machineInShared2)
@@ -160,7 +198,7 @@ func (s *Suite) TestDNSConfigMapResponseWithMagicDNS(c *check.C) {
 		Namespace:      *namespaceShared3,
 		Registered:     true,
 		RegisterMethod: RegisterMethodAuthKey,
-		IPAddress:      "100.64.0.3",
+		IPAddresses:    []netaddr.IP{netaddr.MustParseIP("100.64.0.3")},
 		AuthKeyID:      uint(preAuthKeyInShared3.ID),
 	}
 	app.db.Save(machineInShared3)
@@ -178,7 +216,7 @@ func (s *Suite) TestDNSConfigMapResponseWithMagicDNS(c *check.C) {
 		Namespace:      *namespaceShared1,
 		Registered:     true,
 		RegisterMethod: RegisterMethodAuthKey,
-		IPAddress:      "100.64.0.4",
+		IPAddresses:    []netaddr.IP{netaddr.MustParseIP("100.64.0.4")},
 		AuthKeyID:      uint(PreAuthKey2InShared1.ID),
 	}
 	app.db.Save(machine2InShared1)
@@ -273,7 +311,7 @@ func (s *Suite) TestDNSConfigMapResponseWithoutMagicDNS(c *check.C) {
 		Namespace:      *namespaceShared1,
 		Registered:     true,
 		RegisterMethod: RegisterMethodAuthKey,
-		IPAddress:      "100.64.0.1",
+		IPAddresses:    []netaddr.IP{netaddr.MustParseIP("100.64.0.1")},
 		AuthKeyID:      uint(preAuthKeyInShared1.ID),
 	}
 	app.db.Save(machineInShared1)
@@ -291,7 +329,7 @@ func (s *Suite) TestDNSConfigMapResponseWithoutMagicDNS(c *check.C) {
 		Namespace:      *namespaceShared2,
 		Registered:     true,
 		RegisterMethod: RegisterMethodAuthKey,
-		IPAddress:      "100.64.0.2",
+		IPAddresses:    []netaddr.IP{netaddr.MustParseIP("100.64.0.2")},
 		AuthKeyID:      uint(preAuthKeyInShared2.ID),
 	}
 	app.db.Save(machineInShared2)
@@ -309,7 +347,7 @@ func (s *Suite) TestDNSConfigMapResponseWithoutMagicDNS(c *check.C) {
 		Namespace:      *namespaceShared3,
 		Registered:     true,
 		RegisterMethod: RegisterMethodAuthKey,
-		IPAddress:      "100.64.0.3",
+		IPAddresses:    []netaddr.IP{netaddr.MustParseIP("100.64.0.3")},
 		AuthKeyID:      uint(preAuthKeyInShared3.ID),
 	}
 	app.db.Save(machineInShared3)
@@ -327,7 +365,7 @@ func (s *Suite) TestDNSConfigMapResponseWithoutMagicDNS(c *check.C) {
 		Namespace:      *namespaceShared1,
 		Registered:     true,
 		RegisterMethod: RegisterMethodAuthKey,
-		IPAddress:      "100.64.0.4",
+		IPAddresses:    []netaddr.IP{netaddr.MustParseIP("100.64.0.4")},
 		AuthKeyID:      uint(preAuthKey2InShared1.ID),
 	}
 	app.db.Save(machine2InShared1)
diff --git a/gen/go/headscale/v1/device.pb.go b/gen/go/headscale/v1/device.pb.go
index 302c2653..a3b5911a 100644
--- a/gen/go/headscale/v1/device.pb.go
+++ b/gen/go/headscale/v1/device.pb.go
@@ -1,7 +1,7 @@
 // Code generated by protoc-gen-go. DO NOT EDIT.
 // versions:
 // 	protoc-gen-go v1.27.1
-// 	protoc        v3.18.1
+// 	protoc        v3.17.3
 // source: headscale/v1/device.proto
 
 package v1
diff --git a/gen/go/headscale/v1/headscale.pb.go b/gen/go/headscale/v1/headscale.pb.go
index dd27265d..ad8a50d7 100644
--- a/gen/go/headscale/v1/headscale.pb.go
+++ b/gen/go/headscale/v1/headscale.pb.go
@@ -1,7 +1,7 @@
 // Code generated by protoc-gen-go. DO NOT EDIT.
 // versions:
 // 	protoc-gen-go v1.27.1
-// 	protoc        v3.18.1
+// 	protoc        v3.17.3
 // source: headscale/v1/headscale.proto
 
 package v1
diff --git a/gen/go/headscale/v1/machine.pb.go b/gen/go/headscale/v1/machine.pb.go
index deafbe5c..07613697 100644
--- a/gen/go/headscale/v1/machine.pb.go
+++ b/gen/go/headscale/v1/machine.pb.go
@@ -1,7 +1,7 @@
 // Code generated by protoc-gen-go. DO NOT EDIT.
 // versions:
 // 	protoc-gen-go v1.27.1
-// 	protoc        v3.18.1
+// 	protoc        v3.17.3
 // source: headscale/v1/machine.proto
 
 package v1
@@ -82,7 +82,7 @@ type Machine struct {
 	MachineKey           string                 `protobuf:"bytes,2,opt,name=machine_key,json=machineKey,proto3" json:"machine_key,omitempty"`
 	NodeKey              string                 `protobuf:"bytes,3,opt,name=node_key,json=nodeKey,proto3" json:"node_key,omitempty"`
 	DiscoKey             string                 `protobuf:"bytes,4,opt,name=disco_key,json=discoKey,proto3" json:"disco_key,omitempty"`
-	IpAddress            string                 `protobuf:"bytes,5,opt,name=ip_address,json=ipAddress,proto3" json:"ip_address,omitempty"`
+	IpAddresses          []string               `protobuf:"bytes,5,rep,name=ip_addresses,json=ipAddresses,proto3" json:"ip_addresses,omitempty"`
 	Name                 string                 `protobuf:"bytes,6,opt,name=name,proto3" json:"name,omitempty"`
 	Namespace            *Namespace             `protobuf:"bytes,7,opt,name=namespace,proto3" json:"namespace,omitempty"`
 	Registered           bool                   `protobuf:"varint,8,opt,name=registered,proto3" json:"registered,omitempty"`
@@ -154,11 +154,11 @@ func (x *Machine) GetDiscoKey() string {
 	return ""
 }
 
-func (x *Machine) GetIpAddress() string {
+func (x *Machine) GetIpAddresses() []string {
 	if x != nil {
-		return x.IpAddress
+		return x.IpAddresses
 	}
-	return ""
+	return nil
 }
 
 func (x *Machine) GetName() string {
@@ -1026,129 +1026,129 @@ var file_headscale_v1_machine_proto_rawDesc = []byte{
 	0x64, 0x73, 0x63, 0x61, 0x6c, 0x65, 0x2f, 0x76, 0x31, 0x2f, 0x6e, 0x61, 0x6d, 0x65, 0x73, 0x70,
 	0x61, 0x63, 0x65, 0x2e, 0x70, 0x72, 0x6f, 0x74, 0x6f, 0x1a, 0x1d, 0x68, 0x65, 0x61, 0x64, 0x73,
 	0x63, 0x61, 0x6c, 0x65, 0x2f, 0x76, 0x31, 0x2f, 0x70, 0x72, 0x65, 0x61, 0x75, 0x74, 0x68, 0x6b,
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+	0x65, 0x79, 0x2e, 0x70, 0x72, 0x6f, 0x74, 0x6f, 0x22, 0xfd, 0x04, 0x0a, 0x07, 0x4d, 0x61, 0x63,
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+	0x10, 0x01, 0x12, 0x17, 0x0a, 0x13, 0x52, 0x45, 0x47, 0x49, 0x53, 0x54, 0x45, 0x52, 0x5f, 0x4d,
+	0x45, 0x54, 0x48, 0x4f, 0x44, 0x5f, 0x43, 0x4c, 0x49, 0x10, 0x02, 0x12, 0x18, 0x0a, 0x14, 0x52,
+	0x45, 0x47, 0x49, 0x53, 0x54, 0x45, 0x52, 0x5f, 0x4d, 0x45, 0x54, 0x48, 0x4f, 0x44, 0x5f, 0x4f,
+	0x49, 0x44, 0x43, 0x10, 0x03, 0x42, 0x29, 0x5a, 0x27, 0x67, 0x69, 0x74, 0x68, 0x75, 0x62, 0x2e,
+	0x63, 0x6f, 0x6d, 0x2f, 0x6a, 0x75, 0x61, 0x6e, 0x66, 0x6f, 0x6e, 0x74, 0x2f, 0x68, 0x65, 0x61,
+	0x64, 0x73, 0x63, 0x61, 0x6c, 0x65, 0x2f, 0x67, 0x65, 0x6e, 0x2f, 0x67, 0x6f, 0x2f, 0x76, 0x31,
+	0x62, 0x06, 0x70, 0x72, 0x6f, 0x74, 0x6f, 0x33,
 }
 
 var (
diff --git a/gen/go/headscale/v1/namespace.pb.go b/gen/go/headscale/v1/namespace.pb.go
index f8af539e..341f8ca0 100644
--- a/gen/go/headscale/v1/namespace.pb.go
+++ b/gen/go/headscale/v1/namespace.pb.go
@@ -1,7 +1,7 @@
 // Code generated by protoc-gen-go. DO NOT EDIT.
 // versions:
 // 	protoc-gen-go v1.27.1
-// 	protoc        v3.18.1
+// 	protoc        v3.17.3
 // source: headscale/v1/namespace.proto
 
 package v1
diff --git a/gen/go/headscale/v1/preauthkey.pb.go b/gen/go/headscale/v1/preauthkey.pb.go
index 82b16bf8..1169a89a 100644
--- a/gen/go/headscale/v1/preauthkey.pb.go
+++ b/gen/go/headscale/v1/preauthkey.pb.go
@@ -1,7 +1,7 @@
 // Code generated by protoc-gen-go. DO NOT EDIT.
 // versions:
 // 	protoc-gen-go v1.27.1
-// 	protoc        v3.18.1
+// 	protoc        v3.17.3
 // source: headscale/v1/preauthkey.proto
 
 package v1
diff --git a/gen/go/headscale/v1/routes.pb.go b/gen/go/headscale/v1/routes.pb.go
index e32e1d15..ba40856d 100644
--- a/gen/go/headscale/v1/routes.pb.go
+++ b/gen/go/headscale/v1/routes.pb.go
@@ -1,7 +1,7 @@
 // Code generated by protoc-gen-go. DO NOT EDIT.
 // versions:
 // 	protoc-gen-go v1.27.1
-// 	protoc        v3.18.1
+// 	protoc        v3.17.3
 // source: headscale/v1/routes.proto
 
 package v1
diff --git a/gen/openapiv2/headscale/v1/headscale.swagger.json b/gen/openapiv2/headscale/v1/headscale.swagger.json
index 2274e22c..f1635ac2 100644
--- a/gen/openapiv2/headscale/v1/headscale.swagger.json
+++ b/gen/openapiv2/headscale/v1/headscale.swagger.json
@@ -775,8 +775,11 @@
         "discoKey": {
           "type": "string"
         },
-        "ipAddress": {
-          "type": "string"
+        "ipAddresses": {
+          "type": "array",
+          "items": {
+            "type": "string"
+          }
         },
         "name": {
           "type": "string"
diff --git a/integration_common_test.go b/integration_common_test.go
index 31bae514..94291fc6 100644
--- a/integration_common_test.go
+++ b/integration_common_test.go
@@ -8,22 +8,48 @@ import (
 	"fmt"
 	"time"
 
+	"inet.af/netaddr"
+
 	"github.com/ory/dockertest/v3"
 	"github.com/ory/dockertest/v3/docker"
 )
 
 const DOCKER_EXECUTE_TIMEOUT = 10 * time.Second
 
+var IpPrefix4 = netaddr.MustParseIPPrefix("100.64.0.0/10")
+var IpPrefix6 = netaddr.MustParseIPPrefix("fd7a:115c:a1e0::/48")
+
+type ExecuteCommandConfig struct {
+	timeout time.Duration
+}
+
+type ExecuteCommandOption func(*ExecuteCommandConfig) error
+
+func ExecuteCommandTimeout(timeout time.Duration) ExecuteCommandOption {
+	return ExecuteCommandOption(func(conf *ExecuteCommandConfig) error {
+		conf.timeout = timeout
+		return nil
+	})
+}
+
 func ExecuteCommand(
 	resource *dockertest.Resource,
 	cmd []string,
 	env []string,
+	options ...ExecuteCommandOption,
 ) (string, error) {
 	var stdout bytes.Buffer
 	var stderr bytes.Buffer
 
-	// TODO(kradalby): Make configurable
-	timeout := DOCKER_EXECUTE_TIMEOUT
+	execConfig := ExecuteCommandConfig{
+		timeout: DOCKER_EXECUTE_TIMEOUT,
+	}
+
+	for _, opt := range options {
+		if err := opt(&execConfig); err != nil {
+			return "", fmt.Errorf("execute-command/options: %w", err)
+		}
+	}
 
 	type result struct {
 		exitCode int
@@ -62,16 +88,33 @@ func ExecuteCommand(
 		}
 
 		return stdout.String(), nil
-	case <-time.After(timeout):
+	case <-time.After(execConfig.timeout):
 
-		return "", fmt.Errorf("command timed out after %s", timeout)
+		return "", fmt.Errorf("command timed out after %s", execConfig.timeout)
 	}
 }
 
 func DockerRestartPolicy(config *docker.HostConfig) {
-	// set AutoRemove to true so that stopped container goes away by itself
-	config.AutoRemove = true
+	// set AutoRemove to true so that stopped container goes away by itself on error *immediately*.
+	// when set to false, containers remain until the end of the integration test.
+	config.AutoRemove = false
 	config.RestartPolicy = docker.RestartPolicy{
 		Name: "no",
 	}
 }
+
+func DockerAllowLocalIPv6(config *docker.HostConfig) {
+	if config.Sysctls == nil {
+		config.Sysctls = make(map[string]string, 1)
+	}
+	config.Sysctls["net.ipv6.conf.all.disable_ipv6"] = "0"
+}
+
+func DockerAllowNetworkAdministration(config *docker.HostConfig) {
+	config.CapAdd = append(config.CapAdd, "NET_ADMIN")
+	config.Mounts = append(config.Mounts, docker.HostMount{
+		Type:   "bind",
+		Source: "/dev/net/tun",
+		Target: "/dev/net/tun",
+	})
+}
diff --git a/integration_test.go b/integration_test.go
index 0379429e..ee89ef28 100644
--- a/integration_test.go
+++ b/integration_test.go
@@ -164,9 +164,7 @@ func (s *IntegrationTestSuite) tailscaleContainer(
 		Name:     hostname,
 		Networks: []*dockertest.Network{&s.network},
 		Cmd: []string{
-			"tailscaled",
-			"--tun=userspace-networking",
-			"--socks5-server=localhost:1055",
+			"tailscaled", "--tun=tsdev",
 		},
 	}
 
@@ -174,6 +172,8 @@ func (s *IntegrationTestSuite) tailscaleContainer(
 		tailscaleBuildOptions,
 		tailscaleOptions,
 		DockerRestartPolicy,
+		DockerAllowLocalIPv6,
+		DockerAllowNetworkAdministration,
 	)
 	if err != nil {
 		log.Fatalf("Could not start resource: %s", err)
@@ -372,70 +372,74 @@ func (s *IntegrationTestSuite) TestListNodes() {
 
 func (s *IntegrationTestSuite) TestGetIpAddresses() {
 	for _, scales := range s.namespaces {
-		ipPrefix := netaddr.MustParseIPPrefix("100.64.0.0/10")
 		ips, err := getIPs(scales.tailscales)
 		assert.Nil(s.T(), err)
 
-		for hostname := range scales.tailscales {
-			s.T().Run(hostname, func(t *testing.T) {
-				ip, ok := ips[hostname]
+		for hostname, _ := range scales.tailscales {
+			ips := ips[hostname]
+			for _, ip := range ips {
+				s.T().Run(hostname, func(t *testing.T) {
+					assert.NotNil(t, ip)
 
-				assert.True(t, ok)
-				assert.NotNil(t, ip)
+					fmt.Printf("IP for %s: %s\n", hostname, ip)
 
-				fmt.Printf("IP for %s: %s\n", hostname, ip)
-
-				// c.Assert(ip.Valid(), check.IsTrue)
-				assert.True(t, ip.Is4())
-				assert.True(t, ipPrefix.Contains(ip))
-			})
+					// c.Assert(ip.Valid(), check.IsTrue)
+					assert.True(t, ip.Is4() || ip.Is6())
+					switch {
+					case ip.Is4():
+						assert.True(t, IpPrefix4.Contains(ip))
+					case ip.Is6():
+						assert.True(t, IpPrefix6.Contains(ip))
+					}
+				})
+			}
 		}
 	}
 }
 
 // TODO(kradalby): fix this test
-// We need some way to impot ipnstate.Status from multiple go packages.
+// We need some way to import ipnstate.Status from multiple go packages.
 // Currently it will only work with 1.18.x since that is the last
 // version we have in go.mod
 // func (s *IntegrationTestSuite) TestStatus() {
-// 	for _, scales := range s.namespaces {
-// 		ips, err := getIPs(scales.tailscales)
-// 		assert.Nil(s.T(), err)
+//	for _, scales := range s.namespaces {
+//		ips, err := getIPs(scales.tailscales)
+//		assert.Nil(s.T(), err)
 //
-// 		for hostname, tailscale := range scales.tailscales {
-// 			s.T().Run(hostname, func(t *testing.T) {
-// 				command := []string{"tailscale", "status", "--json"}
+//		for hostname, tailscale := range scales.tailscales {
+//			s.T().Run(hostname, func(t *testing.T) {
+//				command := []string{"tailscale", "status", "--json"}
 //
-// 				fmt.Printf("Getting status for %s\n", hostname)
-// 				result, err := ExecuteCommand(
-// 					&tailscale,
-// 					command,
-// 					[]string{},
-// 				)
-// 				assert.Nil(t, err)
+//				fmt.Printf("Getting status for %s\n", hostname)
+//				result, err := ExecuteCommand(
+//					&tailscale,
+//					command,
+//					[]string{},
+//				)
+//				assert.Nil(t, err)
 //
-// 				var status ipnstate.Status
-// 				err = json.Unmarshal([]byte(result), &status)
-// 				assert.Nil(s.T(), err)
+//				var status ipnstate.Status
+//				err = json.Unmarshal([]byte(result), &status)
+//				assert.Nil(s.T(), err)
 //
-// 				// TODO(kradalby): Replace this check with peer length of SAME namespace
-// 				// Check if we have as many nodes in status
-// 				// as we have IPs/tailscales
-// 				// lines := strings.Split(result, "\n")
-// 				// assert.Equal(t, len(ips), len(lines)-1)
-// 				// assert.Equal(t, len(scales.tailscales), len(lines)-1)
+//				// TODO(kradalby): Replace this check with peer length of SAME namespace
+//				// Check if we have as many nodes in status
+//				// as we have IPs/tailscales
+//				// lines := strings.Split(result, "\n")
+//				// assert.Equal(t, len(ips), len(lines)-1)
+//				// assert.Equal(t, len(scales.tailscales), len(lines)-1)
 //
-// 				peerIps := getIPsfromIPNstate(status)
+//				peerIps := getIPsfromIPNstate(status)
 //
-// 				// Check that all hosts is present in all hosts status
-// 				for ipHostname, ip := range ips {
-// 					if hostname != ipHostname {
-// 						assert.Contains(t, peerIps, ip)
-// 					}
-// 				}
-// 			})
-// 		}
-// 	}
+//				// Check that all hosts is present in all hosts status
+//				for ipHostname, ip := range ips {
+//					if hostname != ipHostname {
+//						assert.Contains(t, peerIps, ip)
+//					}
+//				}
+//			})
+//		}
+//	}
 // }
 
 func getIPsfromIPNstate(status ipnstate.Status) []netaddr.IP {
@@ -448,16 +452,19 @@ func getIPsfromIPNstate(status ipnstate.Status) []netaddr.IP {
 	return ips
 }
 
-func (s *IntegrationTestSuite) TestPingAllPeers() {
+func (s *IntegrationTestSuite) TestPingAllPeersByAddress() {
 	for _, scales := range s.namespaces {
 		ips, err := getIPs(scales.tailscales)
 		assert.Nil(s.T(), err)
 
 		for hostname, tailscale := range scales.tailscales {
-			for peername, ip := range ips {
-				s.T().Run(fmt.Sprintf("%s-%s", hostname, peername), func(t *testing.T) {
+			for peername, peerIPs := range ips {
+				for i, ip := range peerIPs {
 					// We currently cant ping ourselves, so skip that.
-					if peername != hostname {
+					if peername == hostname {
+						continue
+					}
+					s.T().Run(fmt.Sprintf("%s-%s-%d", hostname, peername, i), func(t *testing.T) {
 						// We are only interested in "direct ping" which means what we
 						// might need a couple of more attempts before reaching the node.
 						command := []string{
@@ -469,9 +476,8 @@ func (s *IntegrationTestSuite) TestPingAllPeers() {
 						}
 
 						fmt.Printf(
-							"Pinging from %s (%s) to %s (%s)\n",
+							"Pinging from %s to %s (%s)\n",
 							hostname,
-							ips[hostname],
 							peername,
 							ip,
 						)
@@ -483,8 +489,8 @@ func (s *IntegrationTestSuite) TestPingAllPeers() {
 						assert.Nil(t, err)
 						fmt.Printf("Result for %s: %s\n", hostname, result)
 						assert.Contains(t, result, "pong")
-					}
-				})
+					})
+				}
 			}
 		}
 	}
@@ -553,17 +559,17 @@ func (s *IntegrationTestSuite) TestSharedNodes() {
 	// TODO(juanfont): We have to find out why do we need to wait
 	time.Sleep(100 * time.Second) // Wait for the nodes to receive updates
 
-	mainIps, err := getIPs(main.tailscales)
-	assert.Nil(s.T(), err)
-
 	sharedIps, err := getIPs(shared.tailscales)
 	assert.Nil(s.T(), err)
 
 	for hostname, tailscale := range main.tailscales {
-		for peername, ip := range sharedIps {
-			s.T().Run(fmt.Sprintf("%s-%s", hostname, peername), func(t *testing.T) {
+		for peername, peerIPs := range sharedIps {
+			for i, ip := range peerIPs {
 				// We currently cant ping ourselves, so skip that.
-				if peername != hostname {
+				if peername == hostname {
+					continue
+				}
+				s.T().Run(fmt.Sprintf("%s-%s-%d", hostname, peername, i), func(t *testing.T) {
 					// We are only interested in "direct ping" which means what we
 					// might need a couple of more attempts before reaching the node.
 					command := []string{
@@ -575,9 +581,8 @@ func (s *IntegrationTestSuite) TestSharedNodes() {
 					}
 
 					fmt.Printf(
-						"Pinging from %s (%s) to %s (%s)\n",
+						"Pinging from %s to %s (%s)\n",
 						hostname,
-						mainIps[hostname],
 						peername,
 						ip,
 					)
@@ -589,8 +594,8 @@ func (s *IntegrationTestSuite) TestSharedNodes() {
 					assert.Nil(t, err)
 					fmt.Printf("Result for %s: %s\n", hostname, result)
 					assert.Contains(t, result, "pong")
-				}
-			})
+				})
+			}
 		}
 	}
 }
@@ -599,9 +604,19 @@ func (s *IntegrationTestSuite) TestTailDrop() {
 	for _, scales := range s.namespaces {
 		ips, err := getIPs(scales.tailscales)
 		assert.Nil(s.T(), err)
-		apiURLs, err := getAPIURLs(scales.tailscales)
 		assert.Nil(s.T(), err)
 
+		retry := func(times int, sleepInverval time.Duration, doWork func() error) (err error) {
+			for attempts := 0; attempts < times; attempts++ {
+				err = doWork()
+				if err == nil {
+					return
+				}
+				time.Sleep(sleepInverval)
+			}
+			return
+		}
+
 		for hostname, tailscale := range scales.tailscales {
 			command := []string{"touch", fmt.Sprintf("/tmp/file_from_%s", hostname)}
 			_, err := ExecuteCommand(
@@ -610,63 +625,31 @@ func (s *IntegrationTestSuite) TestTailDrop() {
 				[]string{},
 			)
 			assert.Nil(s.T(), err)
-			for peername, ip := range ips {
+			for peername, _ := range ips {
+				if peername == hostname {
+					continue
+				}
 				s.T().Run(fmt.Sprintf("%s-%s", hostname, peername), func(t *testing.T) {
-					if peername != hostname {
-						// Under normal circumstances, we should be able to send a file
-						// using `tailscale file cp` - but not in userspace networking mode
-						// So curl!
-						peerAPI, ok := apiURLs[ip]
-						assert.True(t, ok)
-
-						// TODO(juanfont): We still have some issues with the test infrastructure, so
-						// lets run curl multiple times until it works.
-						attempts := 0
-						var err error
-						for {
-							command := []string{
-								"curl",
-								"--retry-connrefused",
-								"--retry-delay",
-								"30",
-								"--retry",
-								"10",
-								"--connect-timeout",
-								"60",
-								"-X",
-								"PUT",
-								"--upload-file",
-								fmt.Sprintf("/tmp/file_from_%s", hostname),
-								fmt.Sprintf(
-									"%s/v0/put/file_from_%s",
-									peerAPI,
-									hostname,
-								),
-							}
-							fmt.Printf(
-								"Sending file from %s (%s) to %s (%s)\n",
-								hostname,
-								ips[hostname],
-								peername,
-								ip,
-							)
-							_, err = ExecuteCommand(
-								&tailscale,
-								command,
-								[]string{"ALL_PROXY=socks5://localhost:1055"},
-							)
-							if err == nil {
-								break
-							} else {
-								time.Sleep(10 * time.Second)
-								attempts++
-								if attempts > 10 {
-									break
-								}
-							}
-						}
-						assert.Nil(t, err)
+					command := []string{
+						"tailscale", "file", "cp",
+						fmt.Sprintf("/tmp/file_from_%s", hostname),
+						fmt.Sprintf("%s:", peername),
 					}
+					retry(10, 1*time.Second, func() error {
+						fmt.Printf(
+							"Sending file from %s to %s\n",
+							hostname,
+							peername,
+						)
+						_, err := ExecuteCommand(
+							&tailscale,
+							command,
+							[]string{},
+							ExecuteCommandTimeout(60*time.Second),
+						)
+						return err
+					})
+					assert.Nil(t, err)
 				})
 			}
 		}
@@ -684,32 +667,70 @@ func (s *IntegrationTestSuite) TestTailDrop() {
 			)
 			assert.Nil(s.T(), err)
 			for peername, ip := range ips {
+				if peername == hostname {
+					continue
+				}
 				s.T().Run(fmt.Sprintf("%s-%s", hostname, peername), func(t *testing.T) {
-					if peername != hostname {
-						command := []string{
-							"ls",
-							fmt.Sprintf("/tmp/file_from_%s", peername),
-						}
-						fmt.Printf(
-							"Checking file in %s (%s) from %s (%s)\n",
-							hostname,
-							ips[hostname],
-							peername,
-							ip,
-						)
-						result, err := ExecuteCommand(
-							&tailscale,
-							command,
-							[]string{},
-						)
-						assert.Nil(t, err)
-						fmt.Printf("Result for %s: %s\n", peername, result)
-						assert.Equal(
-							t,
-							result,
-							fmt.Sprintf("/tmp/file_from_%s\n", peername),
-						)
+					command := []string{
+						"ls",
+						fmt.Sprintf("/tmp/file_from_%s", peername),
 					}
+					fmt.Printf(
+						"Checking file in %s (%s) from %s (%s)\n",
+						hostname,
+						ips[hostname],
+						peername,
+						ip,
+					)
+					result, err := ExecuteCommand(
+						&tailscale,
+						command,
+						[]string{},
+					)
+					assert.Nil(t, err)
+					fmt.Printf("Result for %s: %s\n", peername, result)
+					assert.Equal(
+						t,
+						fmt.Sprintf("/tmp/file_from_%s\n", peername),
+						result,
+					)
+				})
+			}
+		}
+	}
+}
+
+func (s *IntegrationTestSuite) TestPingAllPeersByHostname() {
+	for namespace, scales := range s.namespaces {
+		ips, err := getIPs(scales.tailscales)
+		assert.Nil(s.T(), err)
+		for hostname, tailscale := range scales.tailscales {
+			for peername, _ := range ips {
+				if peername == hostname {
+					continue
+				}
+				s.T().Run(fmt.Sprintf("%s-%s", hostname, peername), func(t *testing.T) {
+					command := []string{
+						"tailscale", "ping",
+						"--timeout=10s",
+						"--c=20",
+						"--until-direct=true",
+						fmt.Sprintf("%s.%s.headscale.net", peername, namespace),
+					}
+
+					fmt.Printf(
+						"Pinging using hostname from %s to %s\n",
+						hostname,
+						peername,
+					)
+					result, err := ExecuteCommand(
+						&tailscale,
+						command,
+						[]string{},
+					)
+					assert.Nil(t, err)
+					fmt.Printf("Result for %s: %s\n", hostname, result)
+					assert.Contains(t, result, "pong")
 				})
 			}
 		}
@@ -721,32 +742,31 @@ func (s *IntegrationTestSuite) TestMagicDNS() {
 		ips, err := getIPs(scales.tailscales)
 		assert.Nil(s.T(), err)
 		for hostname, tailscale := range scales.tailscales {
-			for peername, ip := range ips {
+			for peername, ips := range ips {
+				if peername == hostname {
+					continue
+				}
 				s.T().Run(fmt.Sprintf("%s-%s", hostname, peername), func(t *testing.T) {
-					if peername != hostname {
-						command := []string{
-							"tailscale", "ping",
-							"--timeout=10s",
-							"--c=20",
-							"--until-direct=true",
-							fmt.Sprintf("%s.%s.headscale.net", peername, namespace),
-						}
+					command := []string{
+						"tailscale", "ip",
+						fmt.Sprintf("%s.%s.headscale.net", peername, namespace),
+					}
 
-						fmt.Printf(
-							"Pinging using Hostname (magicdns) from %s (%s) to %s (%s)\n",
-							hostname,
-							ips[hostname],
-							peername,
-							ip,
-						)
-						result, err := ExecuteCommand(
-							&tailscale,
-							command,
-							[]string{},
-						)
-						assert.Nil(t, err)
-						fmt.Printf("Result for %s: %s\n", hostname, result)
-						assert.Contains(t, result, "pong")
+					fmt.Printf(
+						"Resolving name %s from %s\n",
+						peername,
+						hostname,
+					)
+					result, err := ExecuteCommand(
+						&tailscale,
+						command,
+						[]string{},
+					)
+					assert.Nil(t, err)
+					fmt.Printf("Result for %s: %s\n", hostname, result)
+
+					for _, ip := range ips {
+						assert.Contains(t, result, ip.String())
 					}
 				})
 			}
@@ -754,8 +774,8 @@ func (s *IntegrationTestSuite) TestMagicDNS() {
 	}
 }
 
-func getIPs(tailscales map[string]dockertest.Resource) (map[string]netaddr.IP, error) {
-	ips := make(map[string]netaddr.IP)
+func getIPs(tailscales map[string]dockertest.Resource) (map[string][]netaddr.IP, error) {
+	ips := make(map[string][]netaddr.IP)
 	for hostname, tailscale := range tailscales {
 		command := []string{"tailscale", "ip"}
 
@@ -768,12 +788,17 @@ func getIPs(tailscales map[string]dockertest.Resource) (map[string]netaddr.IP, e
 			return nil, err
 		}
 
-		ip, err := netaddr.ParseIP(strings.TrimSuffix(result, "\n"))
-		if err != nil {
-			return nil, err
+		for _, address := range strings.Split(result, "\n") {
+			address = strings.TrimSuffix(address, "\n")
+			if len(address) < 1 {
+				continue
+			}
+			ip, err := netaddr.ParseIP(address)
+			if err != nil {
+				return nil, err
+			}
+			ips[hostname] = append(ips[hostname], ip)
 		}
-
-		ips[hostname] = ip
 	}
 
 	return ips, nil
diff --git a/integration_test/etc/config.yaml b/integration_test/etc/config.yaml
index 6f68f304..63af7ebb 100644
--- a/integration_test/etc/config.yaml
+++ b/integration_test/etc/config.yaml
@@ -2,6 +2,9 @@ log_level: trace
 acl_policy_path: ""
 db_type: sqlite3
 ephemeral_node_inactivity_timeout: 30m
+ip_prefixes:
+  - fd7a:115c:a1e0::/48
+  - 100.64.0.0/10
 dns_config:
   base_domain: headscale.net
   magic_dns: true
diff --git a/machine.go b/machine.go
index de1764e1..64fd11b8 100644
--- a/machine.go
+++ b/machine.go
@@ -1,6 +1,7 @@
 package headscale
 
 import (
+	"database/sql/driver"
 	"encoding/json"
 	"errors"
 	"fmt"
@@ -23,6 +24,7 @@ const (
 	errMachineNotFound            = Error("machine not found")
 	errMachineAlreadyRegistered   = Error("machine already registered")
 	errMachineRouteIsNotAvailable = Error("route is not available on machine")
+	errMachineAddressesInvalid    = Error("failed to parse machine addresses")
 )
 
 // Machine is a Headscale client.
@@ -31,7 +33,7 @@ type Machine struct {
 	MachineKey  string `gorm:"type:varchar(64);unique_index"`
 	NodeKey     string
 	DiscoKey    string
-	IPAddress   string
+	IPAddresses MachineAddresses
 	Name        string
 	NamespaceID uint
 	Namespace   Namespace `gorm:"foreignKey:NamespaceID"`
@@ -64,6 +66,47 @@ func (machine Machine) isRegistered() bool {
 	return machine.Registered
 }
 
+type MachineAddresses []netaddr.IP
+
+func (ma MachineAddresses) ToStringSlice() []string {
+	strSlice := make([]string, 0, len(ma))
+	for _, addr := range ma {
+		strSlice = append(strSlice, addr.String())
+	}
+
+	return strSlice
+}
+
+func (ma *MachineAddresses) Scan(destination interface{}) error {
+	switch value := destination.(type) {
+	case string:
+		addresses := strings.Split(value, ",")
+		*ma = (*ma)[:0]
+		for _, addr := range addresses {
+			if len(addr) < 1 {
+				continue
+			}
+			parsed, err := netaddr.ParseIP(addr)
+			if err != nil {
+				return err
+			}
+			*ma = append(*ma, parsed)
+		}
+
+		return nil
+
+	default:
+		return fmt.Errorf("%w: unexpected data type %T", errMachineAddressesInvalid, destination)
+	}
+}
+
+// Value return json value, implement driver.Valuer interface.
+func (ma MachineAddresses) Value() (driver.Value, error) {
+	addresses := strings.Join(ma.ToStringSlice(), ",")
+
+	return addresses, nil
+}
+
 // isExpired returns whether the machine registration has expired.
 func (machine Machine) isExpired() bool {
 	// If Expiry is not set, the client has not indicated that
@@ -385,14 +428,18 @@ func (h *Headscale) isOutdated(machine *Machine) bool {
 	}
 
 	lastChange := h.getLastStateChange(namespaces...)
+	lastUpdate := machine.CreatedAt
+	if machine.LastSuccessfulUpdate != nil {
+		lastUpdate = *machine.LastSuccessfulUpdate
+	}
 	log.Trace().
 		Caller().
 		Str("machine", machine.Name).
-		Time("last_successful_update", *machine.LastSuccessfulUpdate).
-		Time("last_state_change", lastChange).
+		Time("last_successful_update", lastChange).
+		Time("last_state_change", lastUpdate).
 		Msgf("Checking if %s is missing updates", machine.Name)
 
-	return machine.LastSuccessfulUpdate.Before(lastChange)
+	return lastUpdate.Before(lastChange)
 }
 
 func (machine Machine) String() string {
@@ -478,22 +525,12 @@ func (machine Machine) toNode(
 	}
 
 	addrs := []netaddr.IPPrefix{}
-	ip, err := netaddr.ParseIPPrefix(fmt.Sprintf("%s/32", machine.IPAddress))
-	if err != nil {
-		log.Trace().
-			Caller().
-			Str("ip", machine.IPAddress).
-			Msgf("Failed to parse IP Prefix from IP: %s", machine.IPAddress)
-
-		return nil, err
+	for _, machineAddress := range machine.IPAddresses {
+		ip := netaddr.IPPrefixFrom(machineAddress, machineAddress.BitLen())
+		addrs = append(addrs, ip)
 	}
-	addrs = append(addrs, ip) // missing the ipv6 ?
 
-	allowedIPs := []netaddr.IPPrefix{}
-	allowedIPs = append(
-		allowedIPs,
-		ip,
-	) // we append the node own IP, as it is required by the clients
+	allowedIPs := append([]netaddr.IPPrefix{}, addrs...) // we append the node own IP, as it is required by the clients
 
 	if includeRoutes {
 		routesStr := []string{}
@@ -600,11 +637,11 @@ func (machine *Machine) toProto() *v1.Machine {
 		Id:         machine.ID,
 		MachineKey: machine.MachineKey,
 
-		NodeKey:   machine.NodeKey,
-		DiscoKey:  machine.DiscoKey,
-		IpAddress: machine.IPAddress,
-		Name:      machine.Name,
-		Namespace: machine.Namespace.toProto(),
+		NodeKey:     machine.NodeKey,
+		DiscoKey:    machine.DiscoKey,
+		IpAddresses: machine.IPAddresses.ToStringSlice(),
+		Name:        machine.Name,
+		Namespace:   machine.Namespace.toProto(),
 
 		Registered: machine.Registered,
 
@@ -703,7 +740,7 @@ func (h *Headscale) RegisterMachine(
 		return nil, err
 	}
 
-	ip, err := h.getAvailableIP()
+	ips, err := h.getAvailableIPs()
 	if err != nil {
 		log.Error().
 			Caller().
@@ -717,10 +754,10 @@ func (h *Headscale) RegisterMachine(
 	log.Trace().
 		Caller().
 		Str("machine", machine.Name).
-		Str("ip", ip.String()).
+		Str("ip", strings.Join(ips.ToStringSlice(), ",")).
 		Msg("Found IP for host")
 
-	machine.IPAddress = ip.String()
+	machine.IPAddresses = ips
 	machine.NamespaceID = namespace.ID
 	machine.Registered = true
 	machine.RegisterMethod = RegisterMethodCLI
@@ -730,7 +767,7 @@ func (h *Headscale) RegisterMachine(
 	log.Trace().
 		Caller().
 		Str("machine", machine.Name).
-		Str("ip", ip.String()).
+		Str("ip", strings.Join(ips.ToStringSlice(), ",")).
 		Msg("Machine registered with the database")
 
 	return machine, nil
diff --git a/machine_test.go b/machine_test.go
index eb090072..1cc4d40c 100644
--- a/machine_test.go
+++ b/machine_test.go
@@ -6,6 +6,7 @@ import (
 	"time"
 
 	"gopkg.in/check.v1"
+	"inet.af/netaddr"
 )
 
 func (s *Suite) TestGetMachine(c *check.C) {
@@ -199,3 +200,24 @@ func (s *Suite) TestExpireMachine(c *check.C) {
 
 	c.Assert(machineFromDB.isExpired(), check.Equals, true)
 }
+
+func (s *Suite) TestSerdeAddressStrignSlice(c *check.C) {
+	input := MachineAddresses([]netaddr.IP{
+		netaddr.MustParseIP("192.0.2.1"),
+		netaddr.MustParseIP("2001:db8::1"),
+	})
+	serialized, err := input.Value()
+	c.Assert(err, check.IsNil)
+	if serial, ok := serialized.(string); ok {
+		c.Assert(serial, check.Equals, "192.0.2.1,2001:db8::1")
+	}
+
+	var deserialized MachineAddresses
+	err = deserialized.Scan(serialized)
+	c.Assert(err, check.IsNil)
+
+	c.Assert(len(deserialized), check.Equals, len(input))
+	for i := range deserialized {
+		c.Assert(deserialized[i], check.Equals, input[i])
+	}
+}
diff --git a/namespaces_test.go b/namespaces_test.go
index 9793e608..d07deb96 100644
--- a/namespaces_test.go
+++ b/namespaces_test.go
@@ -4,6 +4,7 @@ import (
 	"github.com/rs/zerolog/log"
 	"gopkg.in/check.v1"
 	"gorm.io/gorm"
+	"inet.af/netaddr"
 )
 
 func (s *Suite) TestCreateAndDestroyNamespace(c *check.C) {
@@ -146,7 +147,7 @@ func (s *Suite) TestGetMapResponseUserProfiles(c *check.C) {
 		Namespace:      *namespaceShared1,
 		Registered:     true,
 		RegisterMethod: RegisterMethodAuthKey,
-		IPAddress:      "100.64.0.1",
+		IPAddresses:    []netaddr.IP{netaddr.MustParseIP("100.64.0.1")},
 		AuthKeyID:      uint(preAuthKeyShared1.ID),
 	}
 	app.db.Save(machineInShared1)
@@ -164,7 +165,7 @@ func (s *Suite) TestGetMapResponseUserProfiles(c *check.C) {
 		Namespace:      *namespaceShared2,
 		Registered:     true,
 		RegisterMethod: RegisterMethodAuthKey,
-		IPAddress:      "100.64.0.2",
+		IPAddresses:    []netaddr.IP{netaddr.MustParseIP("100.64.0.2")},
 		AuthKeyID:      uint(preAuthKeyShared2.ID),
 	}
 	app.db.Save(machineInShared2)
@@ -182,7 +183,7 @@ func (s *Suite) TestGetMapResponseUserProfiles(c *check.C) {
 		Namespace:      *namespaceShared3,
 		Registered:     true,
 		RegisterMethod: RegisterMethodAuthKey,
-		IPAddress:      "100.64.0.3",
+		IPAddresses:    []netaddr.IP{netaddr.MustParseIP("100.64.0.3")},
 		AuthKeyID:      uint(preAuthKeyShared3.ID),
 	}
 	app.db.Save(machineInShared3)
@@ -200,7 +201,7 @@ func (s *Suite) TestGetMapResponseUserProfiles(c *check.C) {
 		Namespace:      *namespaceShared1,
 		Registered:     true,
 		RegisterMethod: RegisterMethodAuthKey,
-		IPAddress:      "100.64.0.4",
+		IPAddresses:    []netaddr.IP{netaddr.MustParseIP("100.64.0.4")},
 		AuthKeyID:      uint(preAuthKey2Shared1.ID),
 	}
 	app.db.Save(machine2InShared1)
diff --git a/oidc.go b/oidc.go
index 120a4cff..a47863ff 100644
--- a/oidc.go
+++ b/oidc.go
@@ -126,6 +126,7 @@ var oidcCallbackTemplate = template.Must(
 	</html>`),
 )
 
+// TODO: Why is the entire machine registration logic duplicated here?
 // OIDCCallback handles the callback from the OIDC endpoint
 // Retrieves the mkey from the state cache and adds the machine to the users email namespace
 // TODO: A confirmation page for new machines should be added to avoid phishing vulnerabilities
@@ -316,7 +317,7 @@ func (h *Headscale) OIDCCallback(ctx *gin.Context) {
 				return
 			}
 
-			ip, err := h.getAvailableIP()
+			ips, err := h.getAvailableIPs()
 			if err != nil {
 				log.Error().
 					Caller().
@@ -330,7 +331,7 @@ func (h *Headscale) OIDCCallback(ctx *gin.Context) {
 				return
 			}
 
-			machine.IPAddress = ip.String()
+			machine.IPAddresses = ips
 			machine.NamespaceID = namespace.ID
 			machine.Registered = true
 			machine.RegisterMethod = RegisterMethodOIDC
diff --git a/poll.go b/poll.go
index d7aa12e9..bcd6c33f 100644
--- a/poll.go
+++ b/poll.go
@@ -1,8 +1,10 @@
 package headscale
 
 import (
+	"context"
 	"encoding/json"
 	"errors"
+	"fmt"
 	"io"
 	"net/http"
 	"time"
@@ -154,14 +156,33 @@ func (h *Headscale) PollNetMapHandler(ctx *gin.Context) {
 		Str("id", ctx.Param("id")).
 		Str("machine", machine.Name).
 		Msg("Loading or creating update channel")
-	updateChan := make(chan struct{})
 
-	pollDataChan := make(chan []byte)
+	// TODO: could probably remove all that duplication once generics land.
+	closeChanWithLog := func(channel interface{}, name string) {
+		log.Trace().
+			Str("handler", "PollNetMap").
+			Str("machine", machine.Name).
+			Str("channel", "Done").
+			Msg(fmt.Sprintf("Closing %s channel", name))
+
+		switch c := channel.(type) {
+		case (chan struct{}):
+			close(c)
+
+		case (chan []byte):
+			close(c)
+		}
+	}
+
+	const chanSize = 8
+	updateChan := make(chan struct{}, chanSize)
+	defer closeChanWithLog(updateChan, "updateChan")
+
+	pollDataChan := make(chan []byte, chanSize)
+	defer closeChanWithLog(pollDataChan, "pollDataChan")
 
 	keepAliveChan := make(chan []byte)
-
-	cancelKeepAlive := make(chan struct{})
-	defer close(cancelKeepAlive)
+	defer closeChanWithLog(keepAliveChan, "keepAliveChan")
 
 	if req.OmitPeers && !req.Stream {
 		log.Info().
@@ -174,7 +195,7 @@ func (h *Headscale) PollNetMapHandler(ctx *gin.Context) {
 		// even tho the comments in the tailscale code dont explicitly say so.
 		updateRequestsFromNode.WithLabelValues(machine.Name, machine.Namespace.Name, "endpoint-update").
 			Inc()
-		go func() { updateChan <- struct{}{} }()
+		updateChan <- struct{}{}
 
 		return
 	} else if req.OmitPeers && req.Stream {
@@ -195,7 +216,7 @@ func (h *Headscale) PollNetMapHandler(ctx *gin.Context) {
 		Str("handler", "PollNetMap").
 		Str("machine", machine.Name).
 		Msg("Sending initial map")
-	go func() { pollDataChan <- data }()
+	pollDataChan <- data
 
 	log.Info().
 		Str("handler", "PollNetMap").
@@ -203,7 +224,7 @@ func (h *Headscale) PollNetMapHandler(ctx *gin.Context) {
 		Msg("Notifying peers")
 	updateRequestsFromNode.WithLabelValues(machine.Name, machine.Namespace.Name, "full-update").
 		Inc()
-	go func() { updateChan <- struct{}{} }()
+	updateChan <- struct{}{}
 
 	h.PollNetMapStream(
 		ctx,
@@ -213,7 +234,6 @@ func (h *Headscale) PollNetMapHandler(ctx *gin.Context) {
 		pollDataChan,
 		keepAliveChan,
 		updateChan,
-		cancelKeepAlive,
 	)
 	log.Trace().
 		Str("handler", "PollNetMap").
@@ -233,16 +253,20 @@ func (h *Headscale) PollNetMapStream(
 	pollDataChan chan []byte,
 	keepAliveChan chan []byte,
 	updateChan chan struct{},
-	cancelKeepAlive chan struct{},
 ) {
-	go h.scheduledPollWorker(
-		cancelKeepAlive,
-		updateChan,
-		keepAliveChan,
-		machineKey,
-		mapRequest,
-		machine,
-	)
+	{
+		ctx, cancel := context.WithCancel(ctx.Request.Context())
+		defer cancel()
+
+		go h.scheduledPollWorker(
+			ctx,
+			updateChan,
+			keepAliveChan,
+			machineKey,
+			mapRequest,
+			machine,
+		)
+	}
 
 	ctx.Stream(func(writer io.Writer) bool {
 		log.Trace().
@@ -392,10 +416,14 @@ func (h *Headscale) PollNetMapStream(
 			updateRequestsReceivedOnChannel.WithLabelValues(machine.Name, machine.Namespace.Name).
 				Inc()
 			if h.isOutdated(machine) {
+				var lastUpdate time.Time
+				if machine.LastSuccessfulUpdate != nil {
+					lastUpdate = *machine.LastSuccessfulUpdate
+				}
 				log.Debug().
 					Str("handler", "PollNetMapStream").
 					Str("machine", machine.Name).
-					Time("last_successful_update", *machine.LastSuccessfulUpdate).
+					Time("last_successful_update", lastUpdate).
 					Time("last_state_change", h.getLastStateChange(machine.Namespace.Name)).
 					Msgf("There has been updates since the last successful update to %s", machine.Name)
 				data, err := h.getMapResponse(machineKey, mapRequest, machine)
@@ -464,10 +492,14 @@ func (h *Headscale) PollNetMapStream(
 						Msg("Cannot update machine LastSuccessfulUpdate")
 				}
 			} else {
+				var lastUpdate time.Time
+				if machine.LastSuccessfulUpdate != nil {
+					lastUpdate = *machine.LastSuccessfulUpdate
+				}
 				log.Trace().
 					Str("handler", "PollNetMapStream").
 					Str("machine", machine.Name).
-					Time("last_successful_update", *machine.LastSuccessfulUpdate).
+					Time("last_successful_update", lastUpdate).
 					Time("last_state_change", h.getLastStateChange(machine.Namespace.Name)).
 					Msgf("%s is up to date", machine.Name)
 			}
@@ -507,42 +539,13 @@ func (h *Headscale) PollNetMapStream(
 					Msg("Cannot update machine LastSeen")
 			}
 
-			log.Trace().
-				Str("handler", "PollNetMapStream").
-				Str("machine", machine.Name).
-				Str("channel", "Done").
-				Msg("Cancelling keepAlive channel")
-			cancelKeepAlive <- struct{}{}
-
-			log.Trace().
-				Str("handler", "PollNetMapStream").
-				Str("machine", machine.Name).
-				Str("channel", "Done").
-				Msg("Closing update channel")
-			// h.closeUpdateChannel(m)
-			close(updateChan)
-
-			log.Trace().
-				Str("handler", "PollNetMapStream").
-				Str("machine", machine.Name).
-				Str("channel", "Done").
-				Msg("Closing pollData channel")
-			close(pollDataChan)
-
-			log.Trace().
-				Str("handler", "PollNetMapStream").
-				Str("machine", machine.Name).
-				Str("channel", "Done").
-				Msg("Closing keepAliveChan channel")
-			close(keepAliveChan)
-
 			return false
 		}
 	})
 }
 
 func (h *Headscale) scheduledPollWorker(
-	cancelChan <-chan struct{},
+	ctx context.Context,
 	updateChan chan<- struct{},
 	keepAliveChan chan<- []byte,
 	machineKey key.MachinePublic,
@@ -554,7 +557,7 @@ func (h *Headscale) scheduledPollWorker(
 
 	for {
 		select {
-		case <-cancelChan:
+		case <-ctx.Done():
 			return
 
 		case <-keepAliveTicker.C:
diff --git a/proto/headscale/v1/machine.proto b/proto/headscale/v1/machine.proto
index ed99f002..9b032122 100644
--- a/proto/headscale/v1/machine.proto
+++ b/proto/headscale/v1/machine.proto
@@ -18,7 +18,7 @@ message Machine {
     string machine_key  = 2;
     string node_key     = 3;
     string disco_key    = 4;
-    string ip_address   = 5;
+    repeated string ip_addresses   = 5;
     string name         = 6;
     Namespace namespace = 7;
 
diff --git a/sharing_test.go b/sharing_test.go
index fd7634da..b7fef4e2 100644
--- a/sharing_test.go
+++ b/sharing_test.go
@@ -2,6 +2,7 @@ package headscale
 
 import (
 	"gopkg.in/check.v1"
+	"inet.af/netaddr"
 )
 
 func CreateNodeNamespace(
@@ -26,7 +27,7 @@ func CreateNodeNamespace(
 		NamespaceID:    namespace.ID,
 		Registered:     true,
 		RegisterMethod: RegisterMethodAuthKey,
-		IPAddress:      ip,
+		IPAddresses:    []netaddr.IP{netaddr.MustParseIP("100.64.0.1")},
 		AuthKeyID:      uint(pak1.ID),
 	}
 	app.db.Save(machine)
@@ -214,7 +215,7 @@ func (s *Suite) TestComplexSharingAcrossNamespaces(c *check.C) {
 		NamespaceID:    namespace1.ID,
 		Registered:     true,
 		RegisterMethod: RegisterMethodAuthKey,
-		IPAddress:      "100.64.0.4",
+		IPAddresses:    []netaddr.IP{netaddr.MustParseIP("100.64.0.4")},
 		AuthKeyID:      uint(pak4.ID),
 	}
 	app.db.Save(machine4)
@@ -294,7 +295,7 @@ func (s *Suite) TestDeleteSharedMachine(c *check.C) {
 		NamespaceID:    namespace1.ID,
 		Registered:     true,
 		RegisterMethod: RegisterMethodAuthKey,
-		IPAddress:      "100.64.0.4",
+		IPAddresses:    []netaddr.IP{netaddr.MustParseIP("100.64.0.4")},
 		AuthKeyID:      uint(pak4n1.ID),
 	}
 	app.db.Save(machine4)
diff --git a/utils.go b/utils.go
index 7011e63d..9e85599f 100644
--- a/utils.go
+++ b/utils.go
@@ -133,61 +133,78 @@ func encode(
 	return privKey.SealTo(*pubKey, b), nil
 }
 
-func (h *Headscale) getAvailableIP() (*netaddr.IP, error) {
-	ipPrefix := h.cfg.IPPrefix
+func (h *Headscale) getAvailableIPs() (ips MachineAddresses, err error) {
+	ipPrefixes := h.cfg.IPPrefixes
+	for _, ipPrefix := range ipPrefixes {
+		var ip *netaddr.IP
+		ip, err = h.getAvailableIP(ipPrefix)
+		if err != nil {
+			return
+		}
+		ips = append(ips, *ip)
+	}
 
+	return
+}
+
+func GetIPPrefixEndpoints(na netaddr.IPPrefix) (network, broadcast netaddr.IP) {
+	ipRange := na.Range()
+	network = ipRange.From()
+	broadcast = ipRange.To()
+
+	return
+}
+
+// TODO: Is this concurrency safe?
+// What would happen if multiple hosts were to register at the same time?
+// Would we attempt to assign the same addresses to multiple nodes?
+func (h *Headscale) getAvailableIP(ipPrefix netaddr.IPPrefix) (*netaddr.IP, error) {
 	usedIps, err := h.getUsedIPs()
 	if err != nil {
 		return nil, err
 	}
 
+	ipPrefixNetworkAddress, ipPrefixBroadcastAddress := GetIPPrefixEndpoints(ipPrefix)
+
 	// Get the first IP in our prefix
-	ip := ipPrefix.IP()
+	ip := ipPrefixNetworkAddress.Next()
 
 	for {
 		if !ipPrefix.Contains(ip) {
 			return nil, errCouldNotAllocateIP
 		}
 
-		// Some OS (including Linux) does not like when IPs ends with 0 or 255, which
-		// is typically called network or broadcast. Lets avoid them and continue
-		// to look when we get one of those traditionally reserved IPs.
-		ipRaw := ip.As4()
-		if ipRaw[3] == 0 || ipRaw[3] == 255 {
+		switch {
+		case ip.Compare(ipPrefixBroadcastAddress) == 0:
+			fallthrough
+		case containsIPs(usedIps, ip):
+			fallthrough
+		case ip.IsZero() || ip.IsLoopback():
 			ip = ip.Next()
 
 			continue
-		}
 
-		if ip.IsZero() &&
-			ip.IsLoopback() {
-			ip = ip.Next()
-
-			continue
-		}
-
-		if !containsIPs(usedIps, ip) {
+		default:
 			return &ip, nil
 		}
-
-		ip = ip.Next()
 	}
 }
 
 func (h *Headscale) getUsedIPs() ([]netaddr.IP, error) {
-	var addresses []string
-	h.db.Model(&Machine{}).Pluck("ip_address", &addresses)
+	// FIXME: This really deserves a better data model,
+	// but this was quick to get running and it should be enough
+	// to begin experimenting with a dual stack tailnet.
+	var addressesSlices []string
+	h.db.Model(&Machine{}).Pluck("ip_addresses", &addressesSlices)
 
-	ips := make([]netaddr.IP, len(addresses))
-	for index, addr := range addresses {
-		if addr != "" {
-			ip, err := netaddr.ParseIP(addr)
-			if err != nil {
-				return nil, fmt.Errorf("failed to parse ip from database: %w", err)
-			}
-
-			ips[index] = ip
+	ips := make([]netaddr.IP, 0, len(h.cfg.IPPrefixes)*len(addressesSlices))
+	for _, slice := range addressesSlices {
+		var a MachineAddresses
+		err := a.Scan(slice)
+		if err != nil {
+			return nil, fmt.Errorf("failed to read ip from database: %w", err)
 		}
+		ips = append(ips, a...)
 	}
 
 	return ips, nil
diff --git a/utils_test.go b/utils_test.go
index 95722a83..feb44d5a 100644
--- a/utils_test.go
+++ b/utils_test.go
@@ -6,17 +6,18 @@ import (
 )
 
 func (s *Suite) TestGetAvailableIp(c *check.C) {
-	ip, err := app.getAvailableIP()
+	ips, err := app.getAvailableIPs()
 
 	c.Assert(err, check.IsNil)
 
 	expected := netaddr.MustParseIP("10.27.0.1")
 
-	c.Assert(ip.String(), check.Equals, expected.String())
+	c.Assert(len(ips), check.Equals, 1)
+	c.Assert(ips[0].String(), check.Equals, expected.String())
 }
 
 func (s *Suite) TestGetUsedIps(c *check.C) {
-	ip, err := app.getAvailableIP()
+	ips, err := app.getAvailableIPs()
 	c.Assert(err, check.IsNil)
 
 	namespace, err := app.CreateNamespace("test_ip")
@@ -38,22 +39,24 @@ func (s *Suite) TestGetUsedIps(c *check.C) {
 		Registered:     true,
 		RegisterMethod: RegisterMethodAuthKey,
 		AuthKeyID:      uint(pak.ID),
-		IPAddress:      ip.String(),
+		IPAddresses:    ips,
 	}
 	app.db.Save(&machine)
 
-	ips, err := app.getUsedIPs()
+	usedIps, err := app.getUsedIPs()
 
 	c.Assert(err, check.IsNil)
 
 	expected := netaddr.MustParseIP("10.27.0.1")
 
-	c.Assert(ips[0], check.Equals, expected)
+	c.Assert(len(usedIps), check.Equals, 1)
+	c.Assert(usedIps[0], check.Equals, expected)
 
 	machine1, err := app.GetMachineByID(0)
 	c.Assert(err, check.IsNil)
 
-	c.Assert(machine1.IPAddress, check.Equals, expected.String())
+	c.Assert(len(machine1.IPAddresses), check.Equals, 1)
+	c.Assert(machine1.IPAddresses[0], check.Equals, expected)
 }
 
 func (s *Suite) TestGetMultiIp(c *check.C) {
@@ -61,7 +64,7 @@ func (s *Suite) TestGetMultiIp(c *check.C) {
 	c.Assert(err, check.IsNil)
 
 	for index := 1; index <= 350; index++ {
-		ip, err := app.getAvailableIP()
+		ips, err := app.getAvailableIPs()
 		c.Assert(err, check.IsNil)
 
 		pak, err := app.CreatePreAuthKey(namespace.Name, false, false, nil)
@@ -80,59 +83,64 @@ func (s *Suite) TestGetMultiIp(c *check.C) {
 			Registered:     true,
 			RegisterMethod: RegisterMethodAuthKey,
 			AuthKeyID:      uint(pak.ID),
-			IPAddress:      ip.String(),
+			IPAddresses:    ips,
 		}
 		app.db.Save(&machine)
 	}
 
-	ips, err := app.getUsedIPs()
+	usedIps, err := app.getUsedIPs()
 
 	c.Assert(err, check.IsNil)
 
-	c.Assert(len(ips), check.Equals, 350)
+	c.Assert(len(usedIps), check.Equals, 350)
 
-	c.Assert(ips[0], check.Equals, netaddr.MustParseIP("10.27.0.1"))
-	c.Assert(ips[9], check.Equals, netaddr.MustParseIP("10.27.0.10"))
-	c.Assert(ips[300], check.Equals, netaddr.MustParseIP("10.27.1.47"))
+	c.Assert(usedIps[0], check.Equals, netaddr.MustParseIP("10.27.0.1"))
+	c.Assert(usedIps[9], check.Equals, netaddr.MustParseIP("10.27.0.10"))
+	c.Assert(usedIps[300], check.Equals, netaddr.MustParseIP("10.27.1.45"))
 
 	// Check that we can read back the IPs
 	machine1, err := app.GetMachineByID(1)
 	c.Assert(err, check.IsNil)
+	c.Assert(len(machine1.IPAddresses), check.Equals, 1)
 	c.Assert(
-		machine1.IPAddress,
+		machine1.IPAddresses[0],
 		check.Equals,
-		netaddr.MustParseIP("10.27.0.1").String(),
+		netaddr.MustParseIP("10.27.0.1"),
 	)
 
 	machine50, err := app.GetMachineByID(50)
 	c.Assert(err, check.IsNil)
+	c.Assert(len(machine50.IPAddresses), check.Equals, 1)
 	c.Assert(
-		machine50.IPAddress,
+		machine50.IPAddresses[0],
 		check.Equals,
-		netaddr.MustParseIP("10.27.0.50").String(),
+		netaddr.MustParseIP("10.27.0.50"),
 	)
 
-	expectedNextIP := netaddr.MustParseIP("10.27.1.97")
-	nextIP, err := app.getAvailableIP()
+	expectedNextIP := netaddr.MustParseIP("10.27.1.95")
+	nextIP, err := app.getAvailableIPs()
 	c.Assert(err, check.IsNil)
 
-	c.Assert(nextIP.String(), check.Equals, expectedNextIP.String())
+	c.Assert(len(nextIP), check.Equals, 1)
+	c.Assert(nextIP[0].String(), check.Equals, expectedNextIP.String())
 
 	// If we call get Available again, we should receive
 	// the same IP, as it has not been reserved.
-	nextIP2, err := app.getAvailableIP()
+	nextIP2, err := app.getAvailableIPs()
 	c.Assert(err, check.IsNil)
 
-	c.Assert(nextIP2.String(), check.Equals, expectedNextIP.String())
+	c.Assert(len(nextIP2), check.Equals, 1)
+	c.Assert(nextIP2[0].String(), check.Equals, expectedNextIP.String())
 }
 
 func (s *Suite) TestGetAvailableIpMachineWithoutIP(c *check.C) {
-	ip, err := app.getAvailableIP()
+	ips, err := app.getAvailableIPs()
 	c.Assert(err, check.IsNil)
 
 	expected := netaddr.MustParseIP("10.27.0.1")
 
-	c.Assert(ip.String(), check.Equals, expected.String())
+	c.Assert(len(ips), check.Equals, 1)
+	c.Assert(ips[0].String(), check.Equals, expected.String())
 
 	namespace, err := app.CreateNamespace("test_ip")
 	c.Assert(err, check.IsNil)
@@ -156,8 +164,9 @@ func (s *Suite) TestGetAvailableIpMachineWithoutIP(c *check.C) {
 	}
 	app.db.Save(&machine)
 
-	ip2, err := app.getAvailableIP()
+	ips2, err := app.getAvailableIPs()
 	c.Assert(err, check.IsNil)
 
-	c.Assert(ip2.String(), check.Equals, expected.String())
+	c.Assert(len(ips2), check.Equals, 1)
+	c.Assert(ips2[0].String(), check.Equals, expected.String())
 }