diff --git a/.github/workflows/test-integration-v2-TestACLAllowStarDst.yaml b/.github/workflows/test-integration-v2-TestACLAllowStarDst.yaml
new file mode 100644
index 00000000..47a1b60d
--- /dev/null
+++ b/.github/workflows/test-integration-v2-TestACLAllowStarDst.yaml
@@ -0,0 +1,57 @@
+# DO NOT EDIT, generated with cmd/gh-action-integration-generator/main.go
+# To regenerate, run "go generate" in cmd/gh-action-integration-generator/
+
+name: Integration Test v2 - TestACLAllowStarDst
+
+on: [pull_request]
+
+concurrency:
+  group: ${{ github.workflow }}-$${{ github.head_ref || github.run_id }}
+  cancel-in-progress: true
+
+jobs:
+  test:
+    runs-on: ubuntu-latest
+
+    steps:
+      - uses: actions/checkout@v3
+        with:
+          fetch-depth: 2
+
+      - name: Get changed files
+        id: changed-files
+        uses: tj-actions/changed-files@v34
+        with:
+          files: |
+            *.nix
+            go.*
+            **/*.go
+            integration_test/
+            config-example.yaml
+
+      - uses: cachix/install-nix-action@v18
+        if: ${{ env.ACT }} || steps.changed-files.outputs.any_changed == 'true'
+
+      - name: Run general integration tests
+        if: steps.changed-files.outputs.any_changed == 'true'
+        run: |
+            nix develop --command -- docker run \
+              --tty --rm \
+              --volume ~/.cache/hs-integration-go:/go \
+              --name headscale-test-suite \
+              --volume $PWD:$PWD -w $PWD/integration \
+              --volume /var/run/docker.sock:/var/run/docker.sock \
+              --volume $PWD/control_logs:/tmp/control \
+              golang:1 \
+                go test ./... \
+                  -tags ts2019 \
+                  -failfast \
+                  -timeout 120m \
+                  -parallel 1 \
+                  -run "^TestACLAllowStarDst$"
+
+      - uses: actions/upload-artifact@v3
+        if: always() && steps.changed-files.outputs.any_changed == 'true'
+        with:
+          name: logs
+          path: "control_logs/*.log"
diff --git a/.github/workflows/test-integration-v2-TestACLAllowUserDst.yaml b/.github/workflows/test-integration-v2-TestACLAllowUserDst.yaml
new file mode 100644
index 00000000..d745e871
--- /dev/null
+++ b/.github/workflows/test-integration-v2-TestACLAllowUserDst.yaml
@@ -0,0 +1,57 @@
+# DO NOT EDIT, generated with cmd/gh-action-integration-generator/main.go
+# To regenerate, run "go generate" in cmd/gh-action-integration-generator/
+
+name: Integration Test v2 - TestACLAllowUserDst
+
+on: [pull_request]
+
+concurrency:
+  group: ${{ github.workflow }}-$${{ github.head_ref || github.run_id }}
+  cancel-in-progress: true
+
+jobs:
+  test:
+    runs-on: ubuntu-latest
+
+    steps:
+      - uses: actions/checkout@v3
+        with:
+          fetch-depth: 2
+
+      - name: Get changed files
+        id: changed-files
+        uses: tj-actions/changed-files@v34
+        with:
+          files: |
+            *.nix
+            go.*
+            **/*.go
+            integration_test/
+            config-example.yaml
+
+      - uses: cachix/install-nix-action@v18
+        if: ${{ env.ACT }} || steps.changed-files.outputs.any_changed == 'true'
+
+      - name: Run general integration tests
+        if: steps.changed-files.outputs.any_changed == 'true'
+        run: |
+            nix develop --command -- docker run \
+              --tty --rm \
+              --volume ~/.cache/hs-integration-go:/go \
+              --name headscale-test-suite \
+              --volume $PWD:$PWD -w $PWD/integration \
+              --volume /var/run/docker.sock:/var/run/docker.sock \
+              --volume $PWD/control_logs:/tmp/control \
+              golang:1 \
+                go test ./... \
+                  -tags ts2019 \
+                  -failfast \
+                  -timeout 120m \
+                  -parallel 1 \
+                  -run "^TestACLAllowUserDst$"
+
+      - uses: actions/upload-artifact@v3
+        if: always() && steps.changed-files.outputs.any_changed == 'true'
+        with:
+          name: logs
+          path: "control_logs/*.log"
diff --git a/.github/workflows/test-integration-v2-TestACLDenyAllPort80.yaml b/.github/workflows/test-integration-v2-TestACLDenyAllPort80.yaml
new file mode 100644
index 00000000..767aa213
--- /dev/null
+++ b/.github/workflows/test-integration-v2-TestACLDenyAllPort80.yaml
@@ -0,0 +1,57 @@
+# DO NOT EDIT, generated with cmd/gh-action-integration-generator/main.go
+# To regenerate, run "go generate" in cmd/gh-action-integration-generator/
+
+name: Integration Test v2 - TestACLDenyAllPort80
+
+on: [pull_request]
+
+concurrency:
+  group: ${{ github.workflow }}-$${{ github.head_ref || github.run_id }}
+  cancel-in-progress: true
+
+jobs:
+  test:
+    runs-on: ubuntu-latest
+
+    steps:
+      - uses: actions/checkout@v3
+        with:
+          fetch-depth: 2
+
+      - name: Get changed files
+        id: changed-files
+        uses: tj-actions/changed-files@v34
+        with:
+          files: |
+            *.nix
+            go.*
+            **/*.go
+            integration_test/
+            config-example.yaml
+
+      - uses: cachix/install-nix-action@v18
+        if: ${{ env.ACT }} || steps.changed-files.outputs.any_changed == 'true'
+
+      - name: Run general integration tests
+        if: steps.changed-files.outputs.any_changed == 'true'
+        run: |
+            nix develop --command -- docker run \
+              --tty --rm \
+              --volume ~/.cache/hs-integration-go:/go \
+              --name headscale-test-suite \
+              --volume $PWD:$PWD -w $PWD/integration \
+              --volume /var/run/docker.sock:/var/run/docker.sock \
+              --volume $PWD/control_logs:/tmp/control \
+              golang:1 \
+                go test ./... \
+                  -tags ts2019 \
+                  -failfast \
+                  -timeout 120m \
+                  -parallel 1 \
+                  -run "^TestACLDenyAllPort80$"
+
+      - uses: actions/upload-artifact@v3
+        if: always() && steps.changed-files.outputs.any_changed == 'true'
+        with:
+          name: logs
+          path: "control_logs/*.log"
diff --git a/CHANGELOG.md b/CHANGELOG.md
index 34b36fc0..ba8b44f9 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -4,6 +4,8 @@
 
 ### Changes
 
+- Fix longstanding bug that would prevent "\*" from working properly in ACLs (issue [#699](https://github.com/juanfont/headscale/issues/699)) [#1279](https://github.com/juanfont/headscale/pull/1279)
+
 ## 0.21.0 (2023-03-20)
 
 ### Changes
diff --git a/acls.go b/acls.go
index 70295ead..9233cb43 100644
--- a/acls.go
+++ b/acls.go
@@ -179,6 +179,8 @@ func generateACLPeerCacheMap(rules []tailcfg.FilterRule) map[string]map[string]s
 		}
 	}
 
+	log.Trace().Interface("ACL Cache Map", aclCachePeerMap).Msg("ACL Peer Cache Map generated")
+
 	return aclCachePeerMap
 }
 
diff --git a/integration/acl_test.go b/integration/acl_test.go
index ed32a642..d7043249 100644
--- a/integration/acl_test.go
+++ b/integration/acl_test.go
@@ -2,6 +2,7 @@ package integration
 
 import (
 	"fmt"
+	"strings"
 	"testing"
 
 	"github.com/juanfont/headscale"
@@ -32,7 +33,7 @@ func aclScenario(t *testing.T, policy headscale.ACLPolicy) *Scenario {
 			tsic.WithDockerWorkdir("/"),
 		},
 		hsic.WithACLPolicy(&policy),
-		hsic.WithTestName("acldenyallping"),
+		hsic.WithTestName("acl"),
 	)
 	assert.NoError(t, err)
 
@@ -278,3 +279,163 @@ func TestACLAllowUser80Dst(t *testing.T) {
 	err = scenario.Shutdown()
 	assert.NoError(t, err)
 }
+
+func TestACLDenyAllPort80(t *testing.T) {
+	IntegrationSkip(t)
+
+	scenario := aclScenario(t,
+		headscale.ACLPolicy{
+			Groups: map[string][]string{
+				"group:integration-acl-test": {"user1", "user2"},
+			},
+			ACLs: []headscale.ACL{
+				{
+					Action:       "accept",
+					Sources:      []string{"group:integration-acl-test"},
+					Destinations: []string{"*:22"},
+				},
+			},
+		},
+	)
+
+	allClients, err := scenario.ListTailscaleClients()
+	assert.NoError(t, err)
+
+	allHostnames, err := scenario.ListTailscaleClientsFQDNs()
+	assert.NoError(t, err)
+
+	for _, client := range allClients {
+		for _, hostname := range allHostnames {
+			// We will always be allowed to check _self_ so shortcircuit
+			// the test here.
+			if strings.Contains(hostname, client.Hostname()) {
+				continue
+			}
+
+			url := fmt.Sprintf("http://%s/etc/hostname", hostname)
+			t.Logf("url from %s to %s", client.Hostname(), url)
+
+			result, err := client.Curl(url)
+			assert.Empty(t, result)
+			assert.Error(t, err)
+		}
+	}
+
+	err = scenario.Shutdown()
+	assert.NoError(t, err)
+}
+
+// Test to confirm that we can use user:* from one user.
+// This ACL will not allow user1 access its own machines.
+// Reported: https://github.com/juanfont/headscale/issues/699
+func TestACLAllowUserDst(t *testing.T) {
+	IntegrationSkip(t)
+
+	scenario := aclScenario(t,
+		headscale.ACLPolicy{
+			ACLs: []headscale.ACL{
+				{
+					Action:       "accept",
+					Sources:      []string{"user1"},
+					Destinations: []string{"user2:*"},
+				},
+			},
+		},
+	)
+
+	user1Clients, err := scenario.ListTailscaleClients("user1")
+	assert.NoError(t, err)
+
+	user2Clients, err := scenario.ListTailscaleClients("user2")
+	assert.NoError(t, err)
+
+	// Test that user1 can visit all user2
+	for _, client := range user1Clients {
+		for _, peer := range user2Clients {
+			fqdn, err := peer.FQDN()
+			assert.NoError(t, err)
+
+			url := fmt.Sprintf("http://%s/etc/hostname", fqdn)
+			t.Logf("url from %s to %s", client.Hostname(), url)
+
+			result, err := client.Curl(url)
+			assert.Len(t, result, 13)
+			assert.NoError(t, err)
+		}
+	}
+
+	// Test that user2 _cannot_ visit user1
+	for _, client := range user2Clients {
+		for _, peer := range user1Clients {
+			fqdn, err := peer.FQDN()
+			assert.NoError(t, err)
+
+			url := fmt.Sprintf("http://%s/etc/hostname", fqdn)
+			t.Logf("url from %s to %s", client.Hostname(), url)
+
+			result, err := client.Curl(url)
+			assert.Empty(t, result)
+			assert.Error(t, err)
+		}
+	}
+
+	err = scenario.Shutdown()
+	assert.NoError(t, err)
+}
+
+// Test to confirm that we can use *:* from one user
+// Reported: https://github.com/juanfont/headscale/issues/699
+func TestACLAllowStarDst(t *testing.T) {
+	IntegrationSkip(t)
+
+	scenario := aclScenario(t,
+		headscale.ACLPolicy{
+			ACLs: []headscale.ACL{
+				{
+					Action:       "accept",
+					Sources:      []string{"user1"},
+					Destinations: []string{"*:*"},
+				},
+			},
+		},
+	)
+
+	user1Clients, err := scenario.ListTailscaleClients("user1")
+	assert.NoError(t, err)
+
+	user2Clients, err := scenario.ListTailscaleClients("user2")
+	assert.NoError(t, err)
+
+	// Test that user1 can visit all user2
+	for _, client := range user1Clients {
+		for _, peer := range user2Clients {
+			fqdn, err := peer.FQDN()
+			assert.NoError(t, err)
+
+			url := fmt.Sprintf("http://%s/etc/hostname", fqdn)
+			t.Logf("url from %s to %s", client.Hostname(), url)
+
+			result, err := client.Curl(url)
+			assert.Len(t, result, 13)
+			assert.NoError(t, err)
+		}
+	}
+
+	// Test that user2 _cannot_ visit user1
+	for _, client := range user2Clients {
+		for _, peer := range user1Clients {
+			fqdn, err := peer.FQDN()
+			assert.NoError(t, err)
+
+			url := fmt.Sprintf("http://%s/etc/hostname", fqdn)
+			t.Logf("url from %s to %s", client.Hostname(), url)
+
+			result, err := client.Curl(url)
+			assert.Empty(t, result)
+			assert.Error(t, err)
+		}
+	}
+
+	err = scenario.Shutdown()
+	assert.NoError(t, err)
+}
diff --git a/machine.go b/machine.go
index fd6e2ede..146bfcf7 100644
--- a/machine.go
+++ b/machine.go
@@ -243,6 +243,12 @@ func filterMachinesByACL(
 
 		for _, peerIP := range peerIPs {
 			if dstMap, ok := aclPeerCacheMap[peerIP]; ok {
+				// match source and all destination
+				if _, dstOk := dstMap["*"]; dstOk {
+					peers[peer.ID] = peer
+
+					continue
+				}
 				// match return path
 				for _, machineIP := range machineIPs {
 					if _, dstOk := dstMap[machineIP]; dstOk {
diff --git a/machine_test.go b/machine_test.go
index 86eb1913..c25f32da 100644
--- a/machine_test.go
+++ b/machine_test.go
@@ -282,10 +282,10 @@ func (s *Suite) TestGetACLFilteredPeers(c *check.C) {
 	peersOfAdminMachine := app.filterMachinesByACL(adminMachine, machines)
 
 	c.Log(peersOfTestMachine)
-	c.Assert(len(peersOfTestMachine), check.Equals, 4)
-	c.Assert(peersOfTestMachine[0].Hostname, check.Equals, "testmachine4")
-	c.Assert(peersOfTestMachine[1].Hostname, check.Equals, "testmachine6")
-	c.Assert(peersOfTestMachine[3].Hostname, check.Equals, "testmachine10")
+	c.Assert(len(peersOfTestMachine), check.Equals, 9)
+	c.Assert(peersOfTestMachine[0].Hostname, check.Equals, "testmachine1")
+	c.Assert(peersOfTestMachine[1].Hostname, check.Equals, "testmachine3")
+	c.Assert(peersOfTestMachine[3].Hostname, check.Equals, "testmachine5")
 
 	c.Log(peersOfAdminMachine)
 	c.Assert(len(peersOfAdminMachine), check.Equals, 9)
@@ -950,6 +950,96 @@ func Test_getFilteredByACLPeers(t *testing.T) {
 			},
 			want: Machines{},
 		},
+		{
+			// Investigating 699
+			// Found some machines: [ts-head-8w6paa ts-unstable-lys2ib ts-head-upcrmb ts-unstable-rlwpvr] machine=ts-head-8w6paa
+			// ACL rules generated ACL=[{"DstPorts":[{"Bits":null,"IP":"*","Ports":{"First":0,"Last":65535}}],"SrcIPs":["fd7a:115c:a1e0::3","100.64.0.3","fd7a:115c:a1e0::4","100.64.0.4"]}]
+			// ACL Cache Map={"100.64.0.3":{"*":{}},"100.64.0.4":{"*":{}},"fd7a:115c:a1e0::3":{"*":{}},"fd7a:115c:a1e0::4":{"*":{}}}
+			name: "issue-699-broken-star",
+			args: args{
+				machines: Machines{ //
+					{
+						ID:       1,
+						Hostname: "ts-head-upcrmb",
+						IPAddresses: MachineAddresses{
+							netip.MustParseAddr("100.64.0.3"),
+							netip.MustParseAddr("fd7a:115c:a1e0::3"),
+						},
+						User: User{Name: "user1"},
+					},
+					{
+						ID:       2,
+						Hostname: "ts-unstable-rlwpvr",
+						IPAddresses: MachineAddresses{
+							netip.MustParseAddr("100.64.0.4"),
+							netip.MustParseAddr("fd7a:115c:a1e0::4"),
+						},
+						User: User{Name: "user1"},
+					},
+					{
+						ID:       3,
+						Hostname: "ts-head-8w6paa",
+						IPAddresses: MachineAddresses{
+							netip.MustParseAddr("100.64.0.1"),
+							netip.MustParseAddr("fd7a:115c:a1e0::1"),
+						},
+						User: User{Name: "user2"},
+					},
+					{
+						ID:       4,
+						Hostname: "ts-unstable-lys2ib",
+						IPAddresses: MachineAddresses{
+							netip.MustParseAddr("100.64.0.2"),
+							netip.MustParseAddr("fd7a:115c:a1e0::2"),
+						},
+						User: User{Name: "user2"},
+					},
+				},
+				rules: []tailcfg.FilterRule{ // list of all ACLRules registered
+					{
+						DstPorts: []tailcfg.NetPortRange{
+							{
+								IP:    "*",
+								Ports: tailcfg.PortRange{First: 0, Last: 65535},
+							},
+						},
+						SrcIPs: []string{
+							"fd7a:115c:a1e0::3", "100.64.0.3",
+							"fd7a:115c:a1e0::4", "100.64.0.4",
+						},
+					},
+				},
+				machine: &Machine{ // current machine
+					ID:       3,
+					Hostname: "ts-head-8w6paa",
+					IPAddresses: MachineAddresses{
+						netip.MustParseAddr("100.64.0.1"),
+						netip.MustParseAddr("fd7a:115c:a1e0::1"),
+					},
+					User: User{Name: "user2"},
+				},
+			},
+			want: Machines{
+				{
+					ID:       1,
+					Hostname: "ts-head-upcrmb",
+					IPAddresses: MachineAddresses{
+						netip.MustParseAddr("100.64.0.3"),
+						netip.MustParseAddr("fd7a:115c:a1e0::3"),
+					},
+					User: User{Name: "user1"},
+				},
+				{
+					ID:       2,
+					Hostname: "ts-unstable-rlwpvr",
+					IPAddresses: MachineAddresses{
+						netip.MustParseAddr("100.64.0.4"),
+						netip.MustParseAddr("fd7a:115c:a1e0::4"),
+					},
+					User: User{Name: "user1"},
+				},
+			},
+		},
 	}
 	var lock sync.RWMutex
 	for _, tt := range tests {