mkdocs: 0.27.1

Signed-off-by: Kristoffer Dalby <kristoffer@tailscale.com>

.github/workflows/test-integration.yaml

@@ -38,7 +38,9 @@ jobs:
           - TestOIDCAuthenticationWithPKCE
           - TestOIDCReloginSameNodeNewUser
           - TestOIDCFollowUpUrl
+          - TestOIDCMultipleOpenedLoginUrls
           - TestOIDCReloginSameNodeSameUser
+          - TestOIDCExpiryAfterRestart
           - TestAuthWebFlowAuthenticationPingAll
           - TestAuthWebFlowLogoutAndReloginSameUser
           - TestAuthWebFlowLogoutAndReloginNewUser

CHANGELOG.md

@@ -4,8 +4,37 @@
 
 ### Changes
 
+## 0.27.1 (2025-11-11)
+
+**Minimum supported Tailscale client version: v1.64.0**
+
+### Changes
+
 - Expire nodes with a custom timestamp
   [#2828](https://github.com/juanfont/headscale/pull/2828)
+- Fix issue where node expiry was reset when tailscaled restarts
+  [#2875](https://github.com/juanfont/headscale/pull/2875)
+- Fix OIDC authentication when multiple login URLs are opened
+  [#2861](https://github.com/juanfont/headscale/pull/2861)
+- Fix node re-registration failing with expired auth keys
+  [#2859](https://github.com/juanfont/headscale/pull/2859)
+- Remove old unused database tables and indices
+  [#2844](https://github.com/juanfont/headscale/pull/2844)
+  [#2872](https://github.com/juanfont/headscale/pull/2872)
+- Ignore litestream tables during database validation
+  [#2843](https://github.com/juanfont/headscale/pull/2843)
+- Fix exit node visibility to respect ACL rules
+  [#2855](https://github.com/juanfont/headscale/pull/2855)
+- Fix SSH policy becoming empty when unknown user is referenced
+  [#2874](https://github.com/juanfont/headscale/pull/2874)
+- Fix policy validation when using bypass-grpc mode
+  [#2854](https://github.com/juanfont/headscale/pull/2854)
+- Fix autogroup:self interaction with other ACL rules
+  [#2842](https://github.com/juanfont/headscale/pull/2842)
+- Fix flaky DERP map shuffle test
+  [#2848](https://github.com/juanfont/headscale/pull/2848)
+- Use current stable base images for Debian and Alpine containers
+  [#2827](https://github.com/juanfont/headscale/pull/2827)
 
 ## 0.27.0 (2025-10-27)
 
@@ -89,7 +118,8 @@ the code base over time and make it more correct and efficient.
   [#2692](https://github.com/juanfont/headscale/pull/2692)
 - Policy: Zero or empty destination port is no longer allowed
   [#2606](https://github.com/juanfont/headscale/pull/2606)
-- Stricter hostname validation [#2383](https://github.com/juanfont/headscale/pull/2383)
+- Stricter hostname validation
+  [#2383](https://github.com/juanfont/headscale/pull/2383)
   - Hostnames must be valid DNS labels (2-63 characters, alphanumeric and
     hyphens only, cannot start/end with hyphen)
   - **Client Registration (New Nodes)**: Invalid hostnames are automatically
@@ -144,7 +174,8 @@ the code base over time and make it more correct and efficient.
   [#2776](https://github.com/juanfont/headscale/pull/2776)
 - EXPERIMENTAL: Add support for `autogroup:self`
   [#2789](https://github.com/juanfont/headscale/pull/2789)
-- Add healthcheck command [#2659](https://github.com/juanfont/headscale/pull/2659)
+- Add healthcheck command
+  [#2659](https://github.com/juanfont/headscale/pull/2659)
 
 ## 0.26.1 (2025-06-06)
 

docs/ref/routes.md

@@ -216,6 +216,39 @@ nodes.
 }
 ```
 
+### Restrict access to exit nodes per user or group
+
+A user can use _any_ of the available exit nodes with `autogroup:internet`. Alternatively, the ACL snippet below assigns
+each user a specific exit node while hiding all other exit nodes. The user `alice` can only use exit node `exit1` while
+user `bob` can only use exit node `exit2`.
+
+```json title="Assign each user a dedicated exit node"
+{
+  "hosts": {
+    "exit1": "100.64.0.1/32",
+    "exit2": "100.64.0.2/32"
+  },
+  "acls": [
+    {
+      "action": "accept",
+      "src": ["alice@"],
+      "dst": ["exit1:*"]
+    },
+    {
+      "action": "accept",
+      "src": ["bob@"],
+      "dst": ["exit2:*"]
+    }
+  ]
+}
+```
+
+!!! warning
+
+    - The above implementation is Headscale specific and will likely be removed once [support for
+      `via`](https://github.com/juanfont/headscale/issues/2409) is available.
+    - Beware that a user can also connect to any port of the exit node itself.
+
 ### Automatically approve an exit node with auto approvers
 
 The initial setup of an exit node usually requires manual approval on the control server before it can be used by a node

go.mod

@@ -182,7 +182,7 @@ require (
 	github.com/ncruces/go-strftime v1.0.0 // indirect
 	github.com/opencontainers/go-digest v1.0.0 // indirect
 	github.com/opencontainers/image-spec v1.1.1 // indirect
-	github.com/opencontainers/runc v1.3.3 // indirect
+	github.com/opencontainers/runc v1.3.2 // indirect
 	github.com/pelletier/go-toml/v2 v2.2.4 // indirect
 	github.com/petermattis/goid v0.0.0-20250904145737-900bdf8bb490 // indirect
 	github.com/pkg/errors v0.9.1 // indirect

go.sum

@@ -124,6 +124,8 @@ github.com/creachadair/command v0.2.0 h1:qTA9cMMhZePAxFoNdnk6F6nn94s1qPndIg9hJbq
 github.com/creachadair/command v0.2.0/go.mod h1:j+Ar+uYnFsHpkMeV9kGj6lJ45y9u2xqtg8FYy6cm+0o=
 github.com/creachadair/flax v0.0.5 h1:zt+CRuXQASxwQ68e9GHAOnEgAU29nF0zYMHOCrL5wzE=
 github.com/creachadair/flax v0.0.5/go.mod h1:F1PML0JZLXSNDMNiRGK2yjm5f+L9QCHchyHBldFymj8=
+github.com/creachadair/mds v0.25.2 h1:xc0S0AfDq5GX9KUR5sLvi5XjA61/P6S5e0xFs1vA18Q=
+github.com/creachadair/mds v0.25.2/go.mod h1:+s4CFteFRj4eq2KcGHW8Wei3u9NyzSPzNV32EvjyK/Q=
 github.com/creachadair/mds v0.25.10 h1:9k9JB35D1xhOCFl0liBhagBBp8fWWkKZrA7UXsfoHtA=
 github.com/creachadair/mds v0.25.10/go.mod h1:4hatI3hRM+qhzuAmqPRFvaBM8mONkS7nsLxkcuTYUIs=
 github.com/creachadair/taskgroup v0.13.2 h1:3KyqakBuFsm3KkXi/9XIb0QcA8tEzLHLgaoidf0MdVc=
@@ -276,6 +278,8 @@ github.com/jmespath/go-jmespath/internal/testify v1.5.1/go.mod h1:L3OGu8Wl2/fWfC
 github.com/josharian/intern v1.0.0/go.mod h1:5DoeVV0s6jJacbCEi61lwdGj/aVlrQvzHFFd8Hwg//Y=
 github.com/jsimonetti/rtnetlink v1.4.1 h1:JfD4jthWBqZMEffc5RjgmlzpYttAVw1sdnmiNaPO3hE=
 github.com/jsimonetti/rtnetlink v1.4.1/go.mod h1:xJjT7t59UIZ62GLZbv6PLLo8VFrostJMPBAheR6OM8w=
+github.com/klauspost/compress v1.18.0 h1:c/Cqfb0r+Yi+JtIEq73FWXVkRonBlf0CRNYc8Zttxdo=
+github.com/klauspost/compress v1.18.0/go.mod h1:2Pp+KzxcywXVXMr50+X0Q/Lsb43OQHYWRCY2AiWywWQ=
 github.com/klauspost/compress v1.18.1 h1:bcSGx7UbpBqMChDtsF28Lw6v/G94LPrrbMbdC3JH2co=
 github.com/klauspost/compress v1.18.1/go.mod h1:ZQFFVG+MdnR0P+l6wpXgIL4NTtwiKIdBnrBd8Nrxr+0=
 github.com/klauspost/cpuid/v2 v2.0.9/go.mod h1:FInQzS24/EEf25PyTYn52gqo7WaD8xa0213Md/qVLRg=
@@ -350,8 +354,8 @@ github.com/opencontainers/go-digest v1.0.0 h1:apOUWs51W5PlhuyGyz9FCeeBIOUDA/6nW8
 github.com/opencontainers/go-digest v1.0.0/go.mod h1:0JzlMkj0TRzQZfJkVvzbP0HBR3IKzErnv2BNG4W4MAM=
 github.com/opencontainers/image-spec v1.1.1 h1:y0fUlFfIZhPF1W537XOLg0/fcx6zcHCJwooC2xJA040=
 github.com/opencontainers/image-spec v1.1.1/go.mod h1:qpqAh3Dmcf36wStyyWU+kCeDgrGnAve2nCC8+7h8Q0M=
-github.com/opencontainers/runc v1.3.3 h1:qlmBbbhu+yY0QM7jqfuat7M1H3/iXjju3VkP9lkFQr4=
-github.com/opencontainers/runc v1.3.3/go.mod h1:D7rL72gfWxVs9cJ2/AayxB0Hlvn9g0gaF1R7uunumSI=
+github.com/opencontainers/runc v1.3.2 h1:GUwgo0Fx9M/pl2utaSYlJfdBcXAB/CZXDxe322lvJ3Y=
+github.com/opencontainers/runc v1.3.2/go.mod h1:F7UQQEsxcjUNnFpT1qPLHZBKYP7yWwk6hq8suLy9cl0=
 github.com/orisano/pixelmatch v0.0.0-20220722002657-fb0b55479cde/go.mod h1:nZgzbfBr3hhjoZnS66nKrHmduYNpc34ny7RK4z5/HM0=
 github.com/ory/dockertest/v3 v3.12.0 h1:3oV9d0sDzlSQfHtIaB5k6ghUCVMVLpAY8hwrqoCyRCw=
 github.com/ory/dockertest/v3 v3.12.0/go.mod h1:aKNDTva3cp8dwOWwb9cWuX84aH5akkxXRvO7KCwWVjE=
@@ -459,6 +463,8 @@ github.com/tailscale/peercred v0.0.0-20250107143737-35a0c7bd7edc h1:24heQPtnFR+y
 github.com/tailscale/peercred v0.0.0-20250107143737-35a0c7bd7edc/go.mod h1:f93CXfllFsO9ZQVq+Zocb1Gp4G5Fz0b0rXHLOzt/Djc=
 github.com/tailscale/setec v0.0.0-20250305161714-445cadbbca3d h1:mnqtPWYyvNiPU9l9tzO2YbHXU/xV664XthZYA26lOiE=
 github.com/tailscale/setec v0.0.0-20250305161714-445cadbbca3d/go.mod h1:9BzmlFc3OLqLzLTF/5AY+BMs+clxMqyhSGzgXIm8mNI=
+github.com/tailscale/squibble v0.0.0-20250108170732-a4ca58afa694 h1:95eIP97c88cqAFU/8nURjgI9xxPbD+Ci6mY/a79BI/w=
+github.com/tailscale/squibble v0.0.0-20250108170732-a4ca58afa694/go.mod h1:veguaG8tVg1H/JG5RfpoUW41I+O8ClPElo/fTYr8mMk=
 github.com/tailscale/squibble v0.0.0-20251030164342-4d5df9caa993 h1:FyiiAvDAxpB0DrW2GW3KOVfi3YFOtsQUEeFWbf55JJU=
 github.com/tailscale/squibble v0.0.0-20251030164342-4d5df9caa993/go.mod h1:xJkMmR3t+thnUQhA3Q4m2VSlS5pcOq+CIjmU/xfKKx4=
 github.com/tailscale/tailsql v0.0.0-20250421235516-02f85f087b97 h1:JJkDnrAhHvOCttk8z9xeZzcDlzzkRA7+Duxj9cwOyxk=

hscontrol/auth.go

@@ -71,6 +71,13 @@ func (h *Headscale) handleRegister(
 		// We do not look up nodes by [key.MachinePublic] as it might belong to multiple
 		// nodes, separated by users and this path is handling expiring/logout paths.
 		if node, ok := h.state.GetNodeByNodeKey(req.NodeKey); ok {
+			// When tailscaled restarts, it sends RegisterRequest with Auth=nil and Expiry=zero.
+			// Return the current node state without modification.
+			// See: https://github.com/juanfont/headscale/issues/2862
+			if req.Expiry.IsZero() && node.Expiry().Valid() && !node.IsExpired() {
+				return nodeToRegisterResponse(node), nil
+			}
+
 			resp, err := h.handleLogout(node, req, machineKey)
 			if err != nil {
 				return nil, fmt.Errorf("handling existing node: %w", err)
@@ -173,6 +180,7 @@ func (h *Headscale) handleLogout(
 	}
 
 	// If the request expiry is in the past, we consider it a logout.
+	// Zero expiry is handled in handleRegister() before calling this function.
 	if req.Expiry.Before(time.Now()) {
 		log.Debug().
 			Uint64("node.id", node.ID().Uint64()).

hscontrol/auth_test.go

@@ -3004,3 +3004,296 @@ func createTestApp(t *testing.T) *Headscale {
 
 	return app
 }
+
+// TestGitHubIssue2830_NodeRestartWithUsedPreAuthKey tests the scenario reported in
+// https://github.com/juanfont/headscale/issues/2830
+//
+// Scenario:
+// 1. Node registers successfully with a single-use pre-auth key
+// 2. Node is running fine
+// 3. Node restarts (e.g., after headscale upgrade or tailscale container restart)
+// 4. Node sends RegisterRequest with the same pre-auth key
+// 5. BUG: Headscale rejects the request with "authkey expired" or "authkey already used"
+//
+// Expected behavior:
+// When an existing node (identified by matching NodeKey + MachineKey) re-registers
+// with a pre-auth key that it previously used, the registration should succeed.
+// The node is not creating a new registration - it's re-authenticating the same device.
+func TestGitHubIssue2830_NodeRestartWithUsedPreAuthKey(t *testing.T) {
+	t.Parallel()
+
+	app := createTestApp(t)
+
+	// Create user and single-use pre-auth key
+	user := app.state.CreateUserForTest("test-user")
+	pak, err := app.state.CreatePreAuthKey(types.UserID(user.ID), false, false, nil, nil) // reusable=false
+	require.NoError(t, err)
+	require.False(t, pak.Reusable, "key should be single-use for this test")
+
+	machineKey := key.NewMachine()
+	nodeKey := key.NewNode()
+
+	// STEP 1: Initial registration with pre-auth key (simulates fresh node joining)
+	initialReq := tailcfg.RegisterRequest{
+		Auth: &tailcfg.RegisterResponseAuth{
+			AuthKey: pak.Key,
+		},
+		NodeKey: nodeKey.Public(),
+		Hostinfo: &tailcfg.Hostinfo{
+			Hostname: "test-node",
+		},
+		Expiry: time.Now().Add(24 * time.Hour),
+	}
+
+	t.Log("Step 1: Initial registration with pre-auth key")
+	initialResp, err := app.handleRegister(context.Background(), initialReq, machineKey.Public())
+	require.NoError(t, err, "initial registration should succeed")
+	require.NotNil(t, initialResp)
+	assert.True(t, initialResp.MachineAuthorized, "node should be authorized")
+	assert.False(t, initialResp.NodeKeyExpired, "node key should not be expired")
+
+	// Verify node was created in database
+	node, found := app.state.GetNodeByNodeKey(nodeKey.Public())
+	require.True(t, found, "node should exist after initial registration")
+	assert.Equal(t, "test-node", node.Hostname())
+	assert.Equal(t, nodeKey.Public(), node.NodeKey())
+	assert.Equal(t, machineKey.Public(), node.MachineKey())
+
+	// Verify pre-auth key is now marked as used
+	usedPak, err := app.state.GetPreAuthKey(pak.Key)
+	require.NoError(t, err)
+	assert.True(t, usedPak.Used, "pre-auth key should be marked as used after initial registration")
+
+	// STEP 2: Simulate node restart - node sends RegisterRequest again with same pre-auth key
+	// This happens when:
+	// - Tailscale container restarts
+	// - Tailscaled service restarts
+	// - System reboots
+	// The Tailscale client persists the pre-auth key in its state and sends it on every registration
+	t.Log("Step 2: Node restart - re-registration with same (now used) pre-auth key")
+	restartReq := tailcfg.RegisterRequest{
+		Auth: &tailcfg.RegisterResponseAuth{
+			AuthKey: pak.Key, // Same key, now marked as Used=true
+		},
+		NodeKey: nodeKey.Public(), // Same node key
+		Hostinfo: &tailcfg.Hostinfo{
+			Hostname: "test-node",
+		},
+		Expiry: time.Now().Add(24 * time.Hour),
+	}
+
+	// BUG: This fails with "authkey already used" or "authkey expired"
+	// EXPECTED: Should succeed because it's the same node re-registering
+	restartResp, err := app.handleRegister(context.Background(), restartReq, machineKey.Public())
+
+	// This is the assertion that currently FAILS in v0.27.0
+	assert.NoError(t, err, "BUG: existing node re-registration with its own used pre-auth key should succeed")
+	if err != nil {
+		t.Logf("Error received (this is the bug): %v", err)
+		t.Logf("Expected behavior: Node should be able to re-register with the same pre-auth key it used initially")
+		return // Stop here to show the bug clearly
+	}
+
+	require.NotNil(t, restartResp)
+	assert.True(t, restartResp.MachineAuthorized, "node should remain authorized after restart")
+	assert.False(t, restartResp.NodeKeyExpired, "node key should not be expired after restart")
+
+	// Verify it's the same node (not a duplicate)
+	nodeAfterRestart, found := app.state.GetNodeByNodeKey(nodeKey.Public())
+	require.True(t, found, "node should still exist after restart")
+	assert.Equal(t, node.ID(), nodeAfterRestart.ID(), "should be the same node, not a new one")
+	assert.Equal(t, "test-node", nodeAfterRestart.Hostname())
+}
+
+// TestNodeReregistrationWithReusablePreAuthKey tests that reusable keys work correctly
+// for node re-registration.
+func TestNodeReregistrationWithReusablePreAuthKey(t *testing.T) {
+	t.Parallel()
+
+	app := createTestApp(t)
+
+	user := app.state.CreateUserForTest("test-user")
+	pak, err := app.state.CreatePreAuthKey(types.UserID(user.ID), true, false, nil, nil) // reusable=true
+	require.NoError(t, err)
+	require.True(t, pak.Reusable)
+
+	machineKey := key.NewMachine()
+	nodeKey := key.NewNode()
+
+	// Initial registration
+	initialReq := tailcfg.RegisterRequest{
+		Auth: &tailcfg.RegisterResponseAuth{
+			AuthKey: pak.Key,
+		},
+		NodeKey: nodeKey.Public(),
+		Hostinfo: &tailcfg.Hostinfo{
+			Hostname: "reusable-test-node",
+		},
+		Expiry: time.Now().Add(24 * time.Hour),
+	}
+
+	initialResp, err := app.handleRegister(context.Background(), initialReq, machineKey.Public())
+	require.NoError(t, err)
+	require.NotNil(t, initialResp)
+	assert.True(t, initialResp.MachineAuthorized)
+
+	// Node restart - re-registration with reusable key
+	restartReq := tailcfg.RegisterRequest{
+		Auth: &tailcfg.RegisterResponseAuth{
+			AuthKey: pak.Key, // Reusable key
+		},
+		NodeKey: nodeKey.Public(),
+		Hostinfo: &tailcfg.Hostinfo{
+			Hostname: "reusable-test-node",
+		},
+		Expiry: time.Now().Add(24 * time.Hour),
+	}
+
+	restartResp, err := app.handleRegister(context.Background(), restartReq, machineKey.Public())
+	require.NoError(t, err, "reusable key should allow re-registration")
+	require.NotNil(t, restartResp)
+	assert.True(t, restartResp.MachineAuthorized)
+	assert.False(t, restartResp.NodeKeyExpired)
+}
+
+// TestNodeReregistrationWithExpiredPreAuthKey tests that truly expired keys
+// are still rejected even for existing nodes.
+func TestNodeReregistrationWithExpiredPreAuthKey(t *testing.T) {
+	t.Parallel()
+
+	app := createTestApp(t)
+
+	user := app.state.CreateUserForTest("test-user")
+	expiry := time.Now().Add(-1 * time.Hour) // Already expired
+	pak, err := app.state.CreatePreAuthKey(types.UserID(user.ID), true, false, &expiry, nil)
+	require.NoError(t, err)
+
+	machineKey := key.NewMachine()
+	nodeKey := key.NewNode()
+
+	// Try to register with expired key
+	req := tailcfg.RegisterRequest{
+		Auth: &tailcfg.RegisterResponseAuth{
+			AuthKey: pak.Key,
+		},
+		NodeKey: nodeKey.Public(),
+		Hostinfo: &tailcfg.Hostinfo{
+			Hostname: "expired-key-node",
+		},
+		Expiry: time.Now().Add(24 * time.Hour),
+	}
+
+	_, err = app.handleRegister(context.Background(), req, machineKey.Public())
+	assert.Error(t, err, "expired pre-auth key should be rejected")
+	assert.Contains(t, err.Error(), "authkey expired", "error should mention key expiration")
+}
+// TestGitHubIssue2830_ExistingNodeCanReregisterWithUsedPreAuthKey tests that an existing node
+// can re-register using a pre-auth key that's already marked as Used=true, as long as:
+// 1. The node is re-registering with the same MachineKey it originally used
+// 2. The node is using the same pre-auth key it was originally registered with (AuthKeyID matches)
+//
+// This is the fix for GitHub issue #2830: https://github.com/juanfont/headscale/issues/2830
+//
+// Background: When Docker/Kubernetes containers restart, they keep their persistent state
+// (including the MachineKey), but container entrypoints unconditionally run:
+//   tailscale up --authkey=$TS_AUTHKEY
+//
+// This caused nodes to be rejected after restart because the pre-auth key was already
+// marked as Used=true from the initial registration. The fix allows re-registration of
+// existing nodes with their own used keys.
+func TestGitHubIssue2830_ExistingNodeCanReregisterWithUsedPreAuthKey(t *testing.T) {
+	app := createTestApp(t)
+
+	// Create a user
+	user := app.state.CreateUserForTest("testuser")
+
+	// Create a SINGLE-USE pre-auth key (reusable=false)
+	// This is the type of key that triggers the bug in issue #2830
+	preAuthKey, err := app.state.CreatePreAuthKey(types.UserID(user.ID), false, false, nil, nil)
+	require.NoError(t, err)
+	require.False(t, preAuthKey.Reusable, "Pre-auth key must be single-use to test issue #2830")
+	require.False(t, preAuthKey.Used, "Pre-auth key should not be used yet")
+
+	// Generate node keys for the client
+	machineKey := key.NewMachine()
+	nodeKey := key.NewNode()
+
+	// Step 1: Initial registration with the pre-auth key
+	// This simulates the first time the container starts and runs 'tailscale up --authkey=...'
+	initialReq := tailcfg.RegisterRequest{
+		Auth: &tailcfg.RegisterResponseAuth{
+			AuthKey: preAuthKey.Key,
+		},
+		NodeKey: nodeKey.Public(),
+		Hostinfo: &tailcfg.Hostinfo{
+			Hostname: "issue-2830-test-node",
+		},
+		Expiry: time.Now().Add(24 * time.Hour),
+	}
+
+	initialResp, err := app.handleRegisterWithAuthKey(initialReq, machineKey.Public())
+	require.NoError(t, err, "Initial registration should succeed")
+	require.True(t, initialResp.MachineAuthorized, "Node should be authorized after initial registration")
+	require.NotNil(t, initialResp.User, "User should be set in response")
+	require.Equal(t, "testuser", initialResp.User.DisplayName, "User should match the pre-auth key's user")
+
+	// Verify the pre-auth key is now marked as Used
+	updatedKey, err := app.state.GetPreAuthKey(preAuthKey.Key)
+	require.NoError(t, err)
+	require.True(t, updatedKey.Used, "Pre-auth key should be marked as Used after initial registration")
+
+	// Step 2: Container restart scenario
+	// The container keeps its MachineKey (persistent state), but the entrypoint script
+	// unconditionally runs 'tailscale up --authkey=$TS_AUTHKEY' again
+	//
+	// WITHOUT THE FIX: This would fail with "authkey already used" error
+	// WITH THE FIX: This succeeds because it's the same node re-registering with its own key
+
+	// Simulate sending the same RegisterRequest again (same MachineKey, same AuthKey)
+	// This is exactly what happens when a container restarts
+	reregisterReq := tailcfg.RegisterRequest{
+		Auth: &tailcfg.RegisterResponseAuth{
+			AuthKey: preAuthKey.Key, // Same key, now marked as Used=true
+		},
+		NodeKey: nodeKey.Public(), // Same NodeKey
+		Hostinfo: &tailcfg.Hostinfo{
+			Hostname: "issue-2830-test-node",
+		},
+		Expiry: time.Now().Add(24 * time.Hour),
+	}
+
+	reregisterResp, err := app.handleRegisterWithAuthKey(reregisterReq, machineKey.Public()) // Same MachineKey
+	require.NoError(t, err, "Re-registration with same MachineKey and used pre-auth key should succeed (fixes #2830)")
+	require.True(t, reregisterResp.MachineAuthorized, "Node should remain authorized after re-registration")
+	require.NotNil(t, reregisterResp.User, "User should be set in re-registration response")
+	require.Equal(t, "testuser", reregisterResp.User.DisplayName, "User should remain the same")
+
+	// Verify that only ONE node was created (not a duplicate)
+	nodes := app.state.ListNodesByUser(types.UserID(user.ID))
+	require.Equal(t, 1, nodes.Len(), "Should have exactly one node (no duplicates created)")
+	require.Equal(t, "issue-2830-test-node", nodes.At(0).Hostname(), "Node hostname should match")
+
+	// Step 3: Verify that a DIFFERENT machine cannot use the same used key
+	// This ensures we didn't break the security model - only the original node can re-register
+	differentMachineKey := key.NewMachine()
+	differentNodeKey := key.NewNode()
+
+	attackReq := tailcfg.RegisterRequest{
+		Auth: &tailcfg.RegisterResponseAuth{
+			AuthKey: preAuthKey.Key, // Try to use the same key
+		},
+		NodeKey: differentNodeKey.Public(),
+		Hostinfo: &tailcfg.Hostinfo{
+			Hostname: "attacker-node",
+		},
+		Expiry: time.Now().Add(24 * time.Hour),
+	}
+
+	_, err = app.handleRegisterWithAuthKey(attackReq, differentMachineKey.Public())
+	require.Error(t, err, "Different machine should NOT be able to use the same used pre-auth key")
+	require.Contains(t, err.Error(), "already used", "Error should indicate key is already used")
+
+	// Verify still only one node (the original one)
+	nodesAfterAttack := app.state.ListNodesByUser(types.UserID(user.ID))
+	require.Equal(t, 1, nodesAfterAttack.Len(), "Should still have exactly one node (attack prevented)")
+}

hscontrol/db/db.go

@@ -952,6 +952,41 @@ AND auth_key_id NOT IN (
 					return nil
 				},
 			},
+			{
+				// Drop all indices that are no longer in use and has existed.
+				// They potentially still present from broken migrations in the past.
+				// They should all be cleaned up by the db engine, but we are a bit
+				// conservative to ensure all our previous mess is cleaned up.
+				ID: "202511101554-drop-old-idx",
+				Migrate: func(tx *gorm.DB) error {
+					for _, oldIdx := range []struct{ name, table string }{
+						{"idx_namespaces_deleted_at", "namespaces"},
+						{"idx_routes_deleted_at", "routes"},
+						{"idx_shared_machines_deleted_at", "shared_machines"},
+					} {
+						err := tx.Migrator().DropIndex(oldIdx.table, oldIdx.name)
+						if err != nil {
+							log.Trace().
+								Str("index", oldIdx.name).
+								Str("table", oldIdx.table).
+								Err(err).
+								Msg("Error dropping old index, continuing...")
+						}
+					}
+
+					return nil
+				},
+				Rollback: func(tx *gorm.DB) error {
+					return nil
+				},
+			},
+
+			// Migrations **above** this points will be REMOVED in version **0.29.0**
+			// This is to clean up a lot of old migrations that is seldom used
+			// and carries a lot of technical debt.
+			// Any new migrations should be added after the comment below and follow
+			// the rules it sets out.
+
 			// From this point, the following rules must be followed:
 			// - NEVER use gorm.AutoMigrate, write the exact migration steps needed
 			// - AutoMigrate depends on the struct staying exactly the same, which it won't over time.

hscontrol/db/ip.go

@@ -325,7 +325,11 @@ func (db *HSDatabase) BackfillNodeIPs(i *IPAllocator) ([]string, error) {
 			}
 
 			if changed {
-				err := tx.Save(node).Error
+				// Use Updates() with Select() to only update IP fields, avoiding overwriting
+				// other fields like Expiry. We need Select() because Updates() alone skips
+				// zero values, but we DO want to update IPv4/IPv6 to nil when removing them.
+				// See issue #2862.
+				err := tx.Model(node).Select("ipv4", "ipv6").Updates(node).Error
 				if err != nil {
 					return fmt.Errorf("saving node(%d) after adding IPs: %w", node.ID, err)
 				}

hscontrol/db/node.go

@@ -452,13 +452,6 @@ func NodeSetMachineKey(
 	}).Error
 }
 
-// NodeSave saves a node object to the database, prefer to use a specific save method rather
-// than this. It is intended to be used when we are changing or.
-// TODO(kradalby): Remove this func, just use Save.
-func NodeSave(tx *gorm.DB, node *types.Node) error {
-	return tx.Save(node).Error
-}
-
 func generateGivenName(suppliedName string, randomSuffix bool) (string, error) {
 	// Strip invalid DNS characters for givenName
 	suppliedName = strings.ToLower(suppliedName)

hscontrol/db/preauth_keys.go

@@ -145,11 +145,12 @@ func (hsdb *HSDatabase) ExpirePreAuthKey(k *types.PreAuthKey) error {
 
 // UsePreAuthKey marks a PreAuthKey as used.
 func UsePreAuthKey(tx *gorm.DB, k *types.PreAuthKey) error {
-	k.Used = true
-	if err := tx.Save(k).Error; err != nil {
+	err := tx.Model(k).Update("used", true).Error
+	if err != nil {
 		return fmt.Errorf("failed to update key used status in the database: %w", err)
 	}
 
+	k.Used = true
 	return nil
 }
 

hscontrol/db/testdata/sqlite/headscale_0.26.1_dump_schema-to-0.27.0-old-table-cleanup.sql

@@ -31,10 +31,15 @@ CREATE UNIQUE INDEX idx_name_provider_identifier ON users (name,provider_identif
 CREATE UNIQUE INDEX idx_name_no_provider_identifier ON users (name) WHERE provider_identifier IS NULL;
 
 -- Create all the old tables we have had and ensure they are clean up.
-CREATE TABLE `namespaces` (`id` text,PRIMARY KEY (`id`));
+CREATE TABLE `namespaces` (`id` text,`deleted_at` datetime,PRIMARY KEY (`id`));
 CREATE TABLE `machines` (`id` text,PRIMARY KEY (`id`));
 CREATE TABLE `kvs` (`id` text,PRIMARY KEY (`id`));
-CREATE TABLE `shared_machines` (`id` text,PRIMARY KEY (`id`));
+CREATE TABLE `shared_machines` (`id` text,`deleted_at` datetime,PRIMARY KEY (`id`));
 CREATE TABLE `pre_auth_key_acl_tags` (`id` text,PRIMARY KEY (`id`));
-CREATE TABLE `routes` (`id` text,PRIMARY KEY (`id`));
+CREATE TABLE `routes` (`id` text,`deleted_at` datetime,PRIMARY KEY (`id`));
+
+CREATE INDEX `idx_routes_deleted_at` ON `routes`(`deleted_at`);
+CREATE INDEX `idx_namespaces_deleted_at` ON `namespaces`(`deleted_at`);
+CREATE INDEX `idx_shared_machines_deleted_at` ON `shared_machines`(`deleted_at`);
+
 COMMIT;

hscontrol/db/user_update_test.go

@@ -0,0 +1,134 @@
+package db
+
+import (
+	"database/sql"
+	"testing"
+
+	"github.com/juanfont/headscale/hscontrol/types"
+	"github.com/stretchr/testify/assert"
+	"github.com/stretchr/testify/require"
+	"gorm.io/gorm"
+)
+
+// TestUserUpdatePreservesUnchangedFields verifies that updating a user
+// preserves fields that aren't modified. This test validates the fix
+// for using Updates() instead of Save() in UpdateUser-like operations.
+func TestUserUpdatePreservesUnchangedFields(t *testing.T) {
+	database := dbForTest(t)
+
+	// Create a user with all fields set
+	initialUser := types.User{
+		Name:        "testuser",
+		DisplayName: "Test User Display",
+		Email:       "test@example.com",
+		ProviderIdentifier: sql.NullString{
+			String: "provider-123",
+			Valid:  true,
+		},
+	}
+
+	createdUser, err := database.CreateUser(initialUser)
+	require.NoError(t, err)
+	require.NotNil(t, createdUser)
+
+	// Verify initial state
+	assert.Equal(t, "testuser", createdUser.Name)
+	assert.Equal(t, "Test User Display", createdUser.DisplayName)
+	assert.Equal(t, "test@example.com", createdUser.Email)
+	assert.True(t, createdUser.ProviderIdentifier.Valid)
+	assert.Equal(t, "provider-123", createdUser.ProviderIdentifier.String)
+
+	// Simulate what UpdateUser does: load user, modify one field, save
+	_, err = Write(database.DB, func(tx *gorm.DB) (*types.User, error) {
+		user, err := GetUserByID(tx, types.UserID(createdUser.ID))
+		if err != nil {
+			return nil, err
+		}
+
+		// Modify ONLY DisplayName
+		user.DisplayName = "Updated Display Name"
+
+		// This is the line being tested - currently uses Save() which writes ALL fields, potentially overwriting unchanged ones
+		err = tx.Save(user).Error
+		if err != nil {
+			return nil, err
+		}
+
+		return user, nil
+	})
+	require.NoError(t, err)
+
+	// Read user back from database
+	updatedUser, err := Read(database.DB, func(rx *gorm.DB) (*types.User, error) {
+		return GetUserByID(rx, types.UserID(createdUser.ID))
+	})
+	require.NoError(t, err)
+
+	// Verify that DisplayName was updated
+	assert.Equal(t, "Updated Display Name", updatedUser.DisplayName)
+
+	// CRITICAL: Verify that other fields were NOT overwritten
+	// With Save(), these assertions should pass because the user object
+	// was loaded from DB and has all fields populated.
+	// But if Updates() is used, these will also pass (and it's safer).
+	assert.Equal(t, "testuser", updatedUser.Name, "Name should be preserved")
+	assert.Equal(t, "test@example.com", updatedUser.Email, "Email should be preserved")
+	assert.True(t, updatedUser.ProviderIdentifier.Valid, "ProviderIdentifier should be preserved")
+	assert.Equal(t, "provider-123", updatedUser.ProviderIdentifier.String, "ProviderIdentifier value should be preserved")
+}
+
+// TestUserUpdateWithUpdatesMethod tests that using Updates() instead of Save()
+// works correctly and only updates modified fields.
+func TestUserUpdateWithUpdatesMethod(t *testing.T) {
+	database := dbForTest(t)
+
+	// Create a user
+	initialUser := types.User{
+		Name:        "testuser",
+		DisplayName: "Original Display",
+		Email:       "original@example.com",
+		ProviderIdentifier: sql.NullString{
+			String: "provider-abc",
+			Valid:  true,
+		},
+	}
+
+	createdUser, err := database.CreateUser(initialUser)
+	require.NoError(t, err)
+
+	// Update using Updates() method
+	_, err = Write(database.DB, func(tx *gorm.DB) (*types.User, error) {
+		user, err := GetUserByID(tx, types.UserID(createdUser.ID))
+		if err != nil {
+			return nil, err
+		}
+
+		// Modify multiple fields
+		user.DisplayName = "New Display"
+		user.Email = "new@example.com"
+
+		// Use Updates() instead of Save()
+		err = tx.Updates(user).Error
+		if err != nil {
+			return nil, err
+		}
+
+		return user, nil
+	})
+	require.NoError(t, err)
+
+	// Verify changes
+	updatedUser, err := Read(database.DB, func(rx *gorm.DB) (*types.User, error) {
+		return GetUserByID(rx, types.UserID(createdUser.ID))
+	})
+	require.NoError(t, err)
+
+	// Verify updated fields
+	assert.Equal(t, "New Display", updatedUser.DisplayName)
+	assert.Equal(t, "new@example.com", updatedUser.Email)
+
+	// Verify preserved fields
+	assert.Equal(t, "testuser", updatedUser.Name)
+	assert.True(t, updatedUser.ProviderIdentifier.Valid)
+	assert.Equal(t, "provider-abc", updatedUser.ProviderIdentifier.String)
+}

hscontrol/db/users.go

@@ -102,7 +102,8 @@ func RenameUser(tx *gorm.DB, uid types.UserID, newName string) error {
 
 	oldUser.Name = newName
 
-	if err := tx.Save(&oldUser).Error; err != nil {
+	err = tx.Updates(&oldUser).Error
+	if err != nil {
 		return err
 	}
 

hscontrol/oidc.go

@@ -213,7 +213,8 @@ func (a *AuthProviderOIDC) OIDCCallbackHandler(
 		return
 	}
 
-	cookieState, err := req.Cookie("state")
+	stateCookieName := getCookieName("state", state)
+	cookieState, err := req.Cookie(stateCookieName)
 	if err != nil {
 		httpError(writer, NewHTTPError(http.StatusBadRequest, "state not found", err))
 		return
@@ -235,8 +236,13 @@ func (a *AuthProviderOIDC) OIDCCallbackHandler(
 		httpError(writer, err)
 		return
 	}
+	if idToken.Nonce == "" {
+		httpError(writer, NewHTTPError(http.StatusBadRequest, "nonce not found in IDToken", err))
+		return
+	}
 
-	nonce, err := req.Cookie("nonce")
+	nonceCookieName := getCookieName("nonce", idToken.Nonce)
+	nonce, err := req.Cookie(nonceCookieName)
 	if err != nil {
 		httpError(writer, NewHTTPError(http.StatusBadRequest, "nonce not found", err))
 		return
@@ -584,6 +590,11 @@ func renderOIDCCallbackTemplate(
 	return &content, nil
 }
 
+// getCookieName generates a unique cookie name based on a cookie value.
+func getCookieName(baseName, value string) string {
+	return fmt.Sprintf("%s_%s", baseName, value[:6])
+}
+
 func setCSRFCookie(w http.ResponseWriter, r *http.Request, name string) (string, error) {
 	val, err := util.GenerateRandomStringURLSafe(64)
 	if err != nil {
@@ -592,7 +603,7 @@ func setCSRFCookie(w http.ResponseWriter, r *http.Request, name string) (string,
 
 	c := &http.Cookie{
 		Path:     "/oidc/callback",
-		Name:     name,
+		Name:     getCookieName(name, val),
 		Value:    val,
 		MaxAge:   int(time.Hour.Seconds()),
 		Secure:   r.TLS != nil,

hscontrol/policy/policy_test.go

@@ -1353,6 +1353,55 @@ func TestSSHPolicyRules(t *testing.T) {
 				},
 			}},
 		},
+		{
+			name:       "2863-allow-predefined-missing-users",
+			targetNode: taggedClient,
+			peers:      types.Nodes{&nodeUser2},
+			policy: `{
+  "groups": {
+   "group:example-infra": [
+      "user2@",
+      "not-created-yet@",
+    ],
+  },
+  "tagOwners": {
+    "tag:client": [
+      "user2@"
+    ],
+  },
+  "ssh": [
+    // Allow infra to ssh to tag:example-infra server as debian
+    {
+      "action": "accept",
+      "src": [
+        "group:example-infra"
+      ],
+      "dst": [
+        "tag:client",
+      ],
+      "users": [
+        "debian",
+      ],
+    },
+  ],
+}`,
+			wantSSH: &tailcfg.SSHPolicy{Rules: []*tailcfg.SSHRule{
+				{
+					Principals: []*tailcfg.SSHPrincipal{
+						{NodeIP: "100.64.0.2"},
+					},
+					SSHUsers: map[string]string{
+						"debian": "debian",
+					},
+					Action: &tailcfg.SSHAction{
+						Accept:                    true,
+						AllowAgentForwarding:      true,
+						AllowLocalPortForwarding:  true,
+						AllowRemotePortForwarding: true,
+					},
+				},
+			}},
+		},
 	}
 
 	for _, tt := range tests {

hscontrol/policy/v2/filter.go

@@ -316,7 +316,6 @@ func (pol *Policy) compileSSHPolicy(
 		srcIPs, err := rule.Sources.Resolve(pol, users, nodes)
 		if err != nil {
 			log.Trace().Caller().Err(err).Msgf("SSH policy compilation failed resolving source ips for rule %+v", rule)
-			continue // Skip this rule if we can't resolve sources
 		}
 
 		if srcIPs == nil || len(srcIPs.Prefixes()) == 0 {

hscontrol/state/state.go

@@ -300,7 +300,9 @@ func (s *State) UpdateUser(userID types.UserID, updateFn func(*types.User) error
 			return nil, err
 		}
 
-		if err := tx.Save(user).Error; err != nil {
+		// Use Updates() to only update modified fields, preserving unchanged values.
+		err = tx.Updates(user).Error
+		if err != nil {
 			return nil, fmt.Errorf("updating user: %w", err)
 		}
 
@@ -386,7 +388,11 @@ func (s *State) persistNodeToDB(node types.NodeView) (types.NodeView, change.Cha
 
 	nodePtr := node.AsStruct()
 
-	if err := s.db.DB.Save(nodePtr).Error; err != nil {
+	// Use Omit("expiry") to prevent overwriting expiry during MapRequest updates.
+	// Expiry should only be updated through explicit SetNodeExpiry calls or re-registration.
+	// See: https://github.com/juanfont/headscale/issues/2862
+	err := s.db.DB.Omit("expiry").Updates(nodePtr).Error
+	if err != nil {
 		return types.NodeView{}, change.EmptySet, fmt.Errorf("saving node: %w", err)
 	}
 
@@ -1187,9 +1193,10 @@ func (s *State) HandleNodeFromAuthPath(
 			return types.NodeView{}, change.EmptySet, fmt.Errorf("node not found in NodeStore: %d", existingNodeSameUser.ID())
 		}
 
-		// Use the node from UpdateNode to save to database
 		_, err = hsdb.Write(s.db.DB, func(tx *gorm.DB) (*types.Node, error) {
-			if err := tx.Save(updatedNodeView.AsStruct()).Error; err != nil {
+			// Use Updates() to preserve fields not modified by UpdateNode.
+			err := tx.Updates(updatedNodeView.AsStruct()).Error
+			if err != nil {
 				return nil, fmt.Errorf("failed to save node: %w", err)
 			}
 			return nil, nil
@@ -1294,9 +1301,46 @@ func (s *State) HandleNodeFromPreAuthKey(
 		return types.NodeView{}, change.EmptySet, err
 	}
 
-	err = pak.Validate()
-	if err != nil {
-		return types.NodeView{}, change.EmptySet, err
+	// Check if node exists with same machine key before validating the key.
+	// For #2830: container restarts send the same pre-auth key which may be used/expired.
+	// Skip validation for existing nodes re-registering with the same NodeKey, as the
+	// key was only needed for initial authentication. NodeKey rotation requires validation.
+	existingNodeSameUser, existsSameUser := s.nodeStore.GetNodeByMachineKey(machineKey, types.UserID(pak.User.ID))
+
+	// Skip validation only if both the AuthKeyID and NodeKey match (not a rotation).
+	isExistingNodeReregistering := existsSameUser && existingNodeSameUser.Valid() &&
+		existingNodeSameUser.AuthKey().Valid() &&
+		existingNodeSameUser.AuthKeyID().Valid() &&
+		existingNodeSameUser.AuthKeyID().Get() == pak.ID
+
+	// Check if this is a NodeKey rotation (different NodeKey)
+	isNodeKeyRotation := existsSameUser && existingNodeSameUser.Valid() &&
+		existingNodeSameUser.NodeKey() != regReq.NodeKey
+
+	if isExistingNodeReregistering && !isNodeKeyRotation {
+		// Existing node re-registering with same NodeKey: skip validation.
+		// Pre-auth keys are only needed for initial authentication. Critical for
+		// containers that run "tailscale up --authkey=KEY" on every restart.
+		log.Debug().
+			Caller().
+			Uint64("node.id", existingNodeSameUser.ID().Uint64()).
+			Str("node.name", existingNodeSameUser.Hostname()).
+			Str("machine.key", machineKey.ShortString()).
+			Str("node.key.existing", existingNodeSameUser.NodeKey().ShortString()).
+			Str("node.key.request", regReq.NodeKey.ShortString()).
+			Uint64("authkey.id", pak.ID).
+			Bool("authkey.used", pak.Used).
+			Bool("authkey.expired", pak.Expiration != nil && pak.Expiration.Before(time.Now())).
+			Bool("authkey.reusable", pak.Reusable).
+			Bool("nodekey.rotation", isNodeKeyRotation).
+			Msg("Existing node re-registering with same NodeKey and auth key, skipping validation")
+
+	} else {
+		// New node or NodeKey rotation: require valid auth key.
+		err = pak.Validate()
+		if err != nil {
+			return types.NodeView{}, change.EmptySet, err
+		}
 	}
 
 	// Ensure we have a valid hostname - handle nil/empty cases
@@ -1328,9 +1372,6 @@ func (s *State) HandleNodeFromPreAuthKey(
 
 	var finalNode types.NodeView
 
-	// Check if node already exists with same machine key for this user
-	existingNodeSameUser, existsSameUser := s.nodeStore.GetNodeByMachineKey(machineKey, types.UserID(pak.User.ID))
-
 	// If this node exists for this user, update the node in place.
 	if existsSameUser && existingNodeSameUser.Valid() {
 		log.Trace().
@@ -1372,9 +1413,10 @@ func (s *State) HandleNodeFromPreAuthKey(
 			return types.NodeView{}, change.EmptySet, fmt.Errorf("node not found in NodeStore: %d", existingNodeSameUser.ID())
 		}
 
-		// Use the node from UpdateNode to save to database
 		_, err = hsdb.Write(s.db.DB, func(tx *gorm.DB) (*types.Node, error) {
-			if err := tx.Save(updatedNodeView.AsStruct()).Error; err != nil {
+			// Use Updates() to preserve fields not modified by UpdateNode.
+			err := tx.Updates(updatedNodeView.AsStruct()).Error
+			if err != nil {
 				return nil, fmt.Errorf("failed to save node: %w", err)
 			}
 

integration/auth_key_test.go

@@ -223,6 +223,7 @@ func TestAuthKeyLogoutAndReloginNewUser(t *testing.T) {
 
 	scenario, err := NewScenario(spec)
 	require.NoError(t, err)
+
 	defer scenario.ShutdownAssertNoPanics(t)
 
 	err = scenario.CreateHeadscaleEnv([]tsic.Option{},
@@ -454,3 +455,4 @@ func TestAuthKeyLogoutAndReloginSameUserExpiredKey(t *testing.T) {
 		})
 	}
 }
+

integration/auth_oidc_test.go

@@ -953,6 +953,119 @@ func TestOIDCFollowUpUrl(t *testing.T) {
 	}, 10*time.Second, 200*time.Millisecond, "Waiting for expected node list after OIDC login")
 }
 
+// TestOIDCMultipleOpenedLoginUrls tests the scenario:
+// - client (mostly Windows) opens multiple browser tabs with different login URLs
+// - client performs auth on the first opened browser tab
+//
+// This test makes sure that cookies are still valid for the first browser tab.
+func TestOIDCMultipleOpenedLoginUrls(t *testing.T) {
+	IntegrationSkip(t)
+
+	scenario, err := NewScenario(
+		ScenarioSpec{
+			OIDCUsers: []mockoidc.MockUser{
+				oidcMockUser("user1", true),
+			},
+		},
+	)
+
+	require.NoError(t, err)
+	defer scenario.ShutdownAssertNoPanics(t)
+
+	oidcMap := map[string]string{
+		"HEADSCALE_OIDC_ISSUER":             scenario.mockOIDC.Issuer(),
+		"HEADSCALE_OIDC_CLIENT_ID":          scenario.mockOIDC.ClientID(),
+		"CREDENTIALS_DIRECTORY_TEST":        "/tmp",
+		"HEADSCALE_OIDC_CLIENT_SECRET_PATH": "${CREDENTIALS_DIRECTORY_TEST}/hs_client_oidc_secret",
+	}
+
+	err = scenario.CreateHeadscaleEnvWithLoginURL(
+		nil,
+		hsic.WithTestName("oidcauthrelog"),
+		hsic.WithConfigEnv(oidcMap),
+		hsic.WithTLS(),
+		hsic.WithFileInContainer("/tmp/hs_client_oidc_secret", []byte(scenario.mockOIDC.ClientSecret())),
+		hsic.WithEmbeddedDERPServerOnly(),
+	)
+	require.NoError(t, err)
+
+	headscale, err := scenario.Headscale()
+	require.NoError(t, err)
+
+	listUsers, err := headscale.ListUsers()
+	require.NoError(t, err)
+	assert.Empty(t, listUsers)
+
+	ts, err := scenario.CreateTailscaleNode(
+		"unstable",
+		tsic.WithNetwork(scenario.networks[scenario.testDefaultNetwork]),
+	)
+	require.NoError(t, err)
+
+	u1, err := ts.LoginWithURL(headscale.GetEndpoint())
+	require.NoError(t, err)
+
+	u2, err := ts.LoginWithURL(headscale.GetEndpoint())
+	require.NoError(t, err)
+
+	// make sure login URLs are different
+	require.NotEqual(t, u1.String(), u2.String())
+
+	loginClient, err := newLoginHTTPClient(ts.Hostname())
+	require.NoError(t, err)
+
+	// open the first login URL "in browser"
+	_, redirect1, err := doLoginURLWithClient(ts.Hostname(), u1, loginClient, false)
+	require.NoError(t, err)
+	// open the second login URL "in browser"
+	_, redirect2, err := doLoginURLWithClient(ts.Hostname(), u2, loginClient, false)
+	require.NoError(t, err)
+
+	// two valid redirects with different state/nonce params
+	require.NotEqual(t, redirect1.String(), redirect2.String())
+
+	// complete auth with the first opened "browser tab"
+	_, redirect1, err = doLoginURLWithClient(ts.Hostname(), redirect1, loginClient, true)
+	require.NoError(t, err)
+
+	listUsers, err = headscale.ListUsers()
+	require.NoError(t, err)
+	assert.Len(t, listUsers, 1)
+
+	wantUsers := []*v1.User{
+		{
+			Id:         1,
+			Name:       "user1",
+			Email:      "user1@headscale.net",
+			Provider:   "oidc",
+			ProviderId: scenario.mockOIDC.Issuer() + "/user1",
+		},
+	}
+
+	sort.Slice(
+		listUsers, func(i, j int) bool {
+			return listUsers[i].GetId() < listUsers[j].GetId()
+		},
+	)
+
+	if diff := cmp.Diff(
+		wantUsers,
+		listUsers,
+		cmpopts.IgnoreUnexported(v1.User{}),
+		cmpopts.IgnoreFields(v1.User{}, "CreatedAt"),
+	); diff != "" {
+		t.Fatalf("unexpected users: %s", diff)
+	}
+
+	assert.EventuallyWithT(
+		t, func(c *assert.CollectT) {
+			listNodes, err := headscale.ListNodes()
+			assert.NoError(c, err)
+			assert.Len(c, listNodes, 1)
+		}, 10*time.Second, 200*time.Millisecond, "Waiting for expected node list after OIDC login",
+	)
+}
+
 // TestOIDCReloginSameNodeSameUser tests the scenario where a single Tailscale client
 // authenticates using OIDC (OpenID Connect), logs out, and then logs back in as the same user.
 //
@@ -1181,3 +1294,131 @@ func TestOIDCReloginSameNodeSameUser(t *testing.T) {
 		}
 	}, 60*time.Second, 2*time.Second, "validating user1 node is online after same-user OIDC relogin")
 }
+
+// TestOIDCExpiryAfterRestart validates that node expiry is preserved
+// when a tailscaled client restarts and reconnects to headscale.
+//
+// This test reproduces the bug reported in https://github.com/juanfont/headscale/issues/2862
+// where OIDC expiry was reset to 0001-01-01 00:00:00 after tailscaled restart.
+//
+// Test flow:
+// 1. Node logs in with OIDC (gets 72h expiry)
+// 2. Verify expiry is set correctly in headscale
+// 3. Restart tailscaled container (simulates daemon restart)
+// 4. Wait for reconnection
+// 5. Verify expiry is still set correctly (not zero).
+func TestOIDCExpiryAfterRestart(t *testing.T) {
+	IntegrationSkip(t)
+
+	scenario, err := NewScenario(ScenarioSpec{
+		OIDCUsers: []mockoidc.MockUser{
+			oidcMockUser("user1", true),
+		},
+	})
+
+	require.NoError(t, err)
+	defer scenario.ShutdownAssertNoPanics(t)
+
+	oidcMap := map[string]string{
+		"HEADSCALE_OIDC_ISSUER":             scenario.mockOIDC.Issuer(),
+		"HEADSCALE_OIDC_CLIENT_ID":          scenario.mockOIDC.ClientID(),
+		"CREDENTIALS_DIRECTORY_TEST":        "/tmp",
+		"HEADSCALE_OIDC_CLIENT_SECRET_PATH": "${CREDENTIALS_DIRECTORY_TEST}/hs_client_oidc_secret",
+		"HEADSCALE_OIDC_EXPIRY":             "72h",
+	}
+
+	err = scenario.CreateHeadscaleEnvWithLoginURL(
+		nil,
+		hsic.WithTestName("oidcexpiry"),
+		hsic.WithConfigEnv(oidcMap),
+		hsic.WithTLS(),
+		hsic.WithFileInContainer("/tmp/hs_client_oidc_secret", []byte(scenario.mockOIDC.ClientSecret())),
+		hsic.WithEmbeddedDERPServerOnly(),
+		hsic.WithDERPAsIP(),
+	)
+	requireNoErrHeadscaleEnv(t, err)
+
+	headscale, err := scenario.Headscale()
+	require.NoError(t, err)
+
+	// Create and login tailscale client
+	ts, err := scenario.CreateTailscaleNode("unstable", tsic.WithNetwork(scenario.networks[scenario.testDefaultNetwork]))
+	require.NoError(t, err)
+
+	u, err := ts.LoginWithURL(headscale.GetEndpoint())
+	require.NoError(t, err)
+
+	_, err = doLoginURL(ts.Hostname(), u)
+	require.NoError(t, err)
+
+	t.Logf("Validating initial login and expiry at %s", time.Now().Format(TimestampFormat))
+
+	// Verify initial expiry is set
+	var initialExpiry time.Time
+	assert.EventuallyWithT(t, func(ct *assert.CollectT) {
+		nodes, err := headscale.ListNodes()
+		assert.NoError(ct, err)
+		assert.Len(ct, nodes, 1)
+
+		node := nodes[0]
+		assert.NotNil(ct, node.GetExpiry(), "Expiry should be set after OIDC login")
+
+		if node.GetExpiry() != nil {
+			expiryTime := node.GetExpiry().AsTime()
+			assert.False(ct, expiryTime.IsZero(), "Expiry should not be zero time")
+
+			initialExpiry = expiryTime
+			t.Logf("Initial expiry set to: %v (expires in %v)", expiryTime, time.Until(expiryTime))
+		}
+	}, 30*time.Second, 1*time.Second, "validating initial expiry after OIDC login")
+
+	// Now restart the tailscaled container
+	t.Logf("Restarting tailscaled container at %s", time.Now().Format(TimestampFormat))
+
+	err = ts.Restart()
+	require.NoError(t, err, "Failed to restart tailscaled container")
+
+	t.Logf("Tailscaled restarted, waiting for reconnection at %s", time.Now().Format(TimestampFormat))
+
+	// Wait for the node to come back online
+	assert.EventuallyWithT(t, func(ct *assert.CollectT) {
+		status, err := ts.Status()
+		if !assert.NoError(ct, err) {
+			return
+		}
+
+		if !assert.NotNil(ct, status) {
+			return
+		}
+
+		assert.Equal(ct, "Running", status.BackendState)
+	}, 60*time.Second, 2*time.Second, "waiting for tailscale to reconnect after restart")
+
+	// THE CRITICAL TEST: Verify expiry is still set correctly after restart
+	t.Logf("Validating expiry preservation after restart at %s", time.Now().Format(TimestampFormat))
+
+	assert.EventuallyWithT(t, func(ct *assert.CollectT) {
+		nodes, err := headscale.ListNodes()
+		assert.NoError(ct, err)
+		assert.Len(ct, nodes, 1, "Should still have exactly 1 node after restart")
+
+		node := nodes[0]
+		assert.NotNil(ct, node.GetExpiry(), "Expiry should NOT be nil after restart")
+
+		if node.GetExpiry() != nil {
+			expiryTime := node.GetExpiry().AsTime()
+
+			// This is the bug check - expiry should NOT be zero time
+			assert.False(ct, expiryTime.IsZero(),
+				"BUG: Expiry was reset to zero time after tailscaled restart! This is issue #2862")
+
+			// Expiry should be exactly the same as before restart
+			assert.Equal(ct, initialExpiry, expiryTime,
+				"Expiry should be exactly the same after restart, got %v, expected %v",
+				expiryTime, initialExpiry)
+
+			t.Logf("SUCCESS: Expiry preserved after restart: %v (expires in %v)",
+				expiryTime, time.Until(expiryTime))
+		}
+	}, 30*time.Second, 1*time.Second, "validating expiry preservation after restart")
+}

integration/scenario.go

@@ -860,47 +860,183 @@ func (s *Scenario) RunTailscaleUpWithURL(userStr, loginServer string) error {
 	return fmt.Errorf("failed to up tailscale node: %w", errNoUserAvailable)
 }
 
-// doLoginURL visits the given login URL and returns the body as a
-// string.
-func doLoginURL(hostname string, loginURL *url.URL) (string, error) {
-	log.Printf("%s login url: %s\n", hostname, loginURL.String())
+type debugJar struct {
+	inner *cookiejar.Jar
+	mu    sync.RWMutex
+	store map[string]map[string]map[string]*http.Cookie // domain -> path -> name -> cookie
+}
 
-	var err error
+func newDebugJar() (*debugJar, error) {
+	jar, err := cookiejar.New(nil)
+	if err != nil {
+		return nil, err
+	}
+	return &debugJar{
+		inner: jar,
+		store: make(map[string]map[string]map[string]*http.Cookie),
+	}, nil
+}
+
+func (j *debugJar) SetCookies(u *url.URL, cookies []*http.Cookie) {
+	j.inner.SetCookies(u, cookies)
+
+	j.mu.Lock()
+	defer j.mu.Unlock()
+
+	for _, c := range cookies {
+		if c == nil || c.Name == "" {
+			continue
+		}
+		domain := c.Domain
+		if domain == "" {
+			domain = u.Hostname()
+		}
+		path := c.Path
+		if path == "" {
+			path = "/"
+		}
+		if _, ok := j.store[domain]; !ok {
+			j.store[domain] = make(map[string]map[string]*http.Cookie)
+		}
+		if _, ok := j.store[domain][path]; !ok {
+			j.store[domain][path] = make(map[string]*http.Cookie)
+		}
+		j.store[domain][path][c.Name] = copyCookie(c)
+	}
+}
+
+func (j *debugJar) Cookies(u *url.URL) []*http.Cookie {
+	return j.inner.Cookies(u)
+}
+
+func (j *debugJar) Dump(w io.Writer) {
+	j.mu.RLock()
+	defer j.mu.RUnlock()
+
+	for domain, paths := range j.store {
+		fmt.Fprintf(w, "Domain: %s\n", domain)
+		for path, byName := range paths {
+			fmt.Fprintf(w, "  Path: %s\n", path)
+			for _, c := range byName {
+				fmt.Fprintf(
+					w, "    %s=%s; Expires=%v; Secure=%v; HttpOnly=%v; SameSite=%v\n",
+					c.Name, c.Value, c.Expires, c.Secure, c.HttpOnly, c.SameSite,
+				)
+			}
+		}
+	}
+}
+
+func copyCookie(c *http.Cookie) *http.Cookie {
+	cc := *c
+	return &cc
+}
+
+func newLoginHTTPClient(hostname string) (*http.Client, error) {
 	hc := &http.Client{
 		Transport: LoggingRoundTripper{Hostname: hostname},
 	}
-	hc.Jar, err = cookiejar.New(nil)
+
+	jar, err := newDebugJar()
 	if err != nil {
-		return "", fmt.Errorf("%s failed to create cookiejar	: %w", hostname, err)
+		return nil, fmt.Errorf("%s failed to create cookiejar: %w", hostname, err)
+	}
+
+	hc.Jar = jar
+
+	return hc, nil
+}
+
+// doLoginURL visits the given login URL and returns the body as a string.
+func doLoginURL(hostname string, loginURL *url.URL) (string, error) {
+	log.Printf("%s login url: %s\n", hostname, loginURL.String())
+
+	hc, err := newLoginHTTPClient(hostname)
+	if err != nil {
+		return "", err
+	}
+
+	body, _, err := doLoginURLWithClient(hostname, loginURL, hc, true)
+	if err != nil {
+		return "", err
+	}
+
+	return body, nil
+}
+
+// doLoginURLWithClient performs the login request using the provided HTTP client.
+// When followRedirects is false, it will return the first redirect without following it.
+func doLoginURLWithClient(hostname string, loginURL *url.URL, hc *http.Client, followRedirects bool) (
+	string,
+	*url.URL,
+	error,
+) {
+	if hc == nil {
+		return "", nil, fmt.Errorf("%s http client is nil", hostname)
+	}
+
+	if loginURL == nil {
+		return "", nil, fmt.Errorf("%s login url is nil", hostname)
 	}
 
 	log.Printf("%s logging in with url: %s", hostname, loginURL.String())
 	ctx := context.Background()
-	req, _ := http.NewRequestWithContext(ctx, http.MethodGet, loginURL.String(), nil)
+	req, err := http.NewRequestWithContext(ctx, http.MethodGet, loginURL.String(), nil)
+	if err != nil {
+		return "", nil, fmt.Errorf("%s failed to create http request: %w", hostname, err)
+	}
+
+	originalRedirect := hc.CheckRedirect
+	if !followRedirects {
+		hc.CheckRedirect = func(req *http.Request, via []*http.Request) error {
+			return http.ErrUseLastResponse
+		}
+	}
+	defer func() {
+		hc.CheckRedirect = originalRedirect
+	}()
+
 	resp, err := hc.Do(req)
 	if err != nil {
-		return "", fmt.Errorf("%s failed to send http request: %w", hostname, err)
+		return "", nil, fmt.Errorf("%s failed to send http request: %w", hostname, err)
 	}
-
-	log.Printf("cookies: %+v", hc.Jar.Cookies(loginURL))
-
-	if resp.StatusCode != http.StatusOK {
-		body, _ := io.ReadAll(resp.Body)
-		log.Printf("body: %s", body)
-
-		return "", fmt.Errorf("%s response code of login request was %w", hostname, err)
-	}
-
 	defer resp.Body.Close()
 
-	body, err := io.ReadAll(resp.Body)
+	bodyBytes, err := io.ReadAll(resp.Body)
 	if err != nil {
-		log.Printf("%s failed to read response body: %s", hostname, err)
+		return "", nil, fmt.Errorf("%s failed to read response body: %w", hostname, err)
+	}
+	body := string(bodyBytes)
 
-		return "", fmt.Errorf("%s failed to read response body: %w", hostname, err)
+	var redirectURL *url.URL
+	if resp.StatusCode >= http.StatusMultipleChoices && resp.StatusCode < http.StatusBadRequest {
+		redirectURL, err = resp.Location()
+		if err != nil {
+			return body, nil, fmt.Errorf("%s failed to resolve redirect location: %w", hostname, err)
+		}
 	}
 
-	return string(body), nil
+	if followRedirects && resp.StatusCode != http.StatusOK {
+		log.Printf("body: %s", body)
+
+		return body, redirectURL, fmt.Errorf("%s unexpected status code %d", hostname, resp.StatusCode)
+	}
+
+	if resp.StatusCode >= http.StatusBadRequest {
+		log.Printf("body: %s", body)
+
+		return body, redirectURL, fmt.Errorf("%s unexpected status code %d", hostname, resp.StatusCode)
+	}
+
+	if hc.Jar != nil {
+		if jar, ok := hc.Jar.(*debugJar); ok {
+			jar.Dump(os.Stdout)
+		} else {
+			log.Printf("cookies: %+v", hc.Jar.Cookies(loginURL))
+		}
+	}
+
+	return body, redirectURL, nil
 }
 
 var errParseAuthPage = errors.New("failed to parse auth page")

integration/tailscale.go

@@ -29,6 +29,7 @@ type TailscaleClient interface {
 	Login(loginServer, authKey string) error
 	LoginWithURL(loginServer string) (*url.URL, error)
 	Logout() error
+	Restart() error
 	Up() error
 	Down() error
 	IPs() ([]netip.Addr, error)

integration/tsic/tsic.go

@@ -555,6 +555,39 @@ func (t *TailscaleInContainer) Logout() error {
 	return t.waitForBackendState("NeedsLogin", integrationutil.PeerSyncTimeout())
 }
 
+// Restart restarts the Tailscale container using Docker API.
+// This simulates a container restart (e.g., docker restart or Kubernetes pod restart).
+// The container's entrypoint will re-execute, which typically includes running
+// "tailscale up" with any auth keys stored in environment variables.
+func (t *TailscaleInContainer) Restart() error {
+	if t.container == nil {
+		return fmt.Errorf("container not initialized")
+	}
+
+	// Use Docker API to restart the container
+	err := t.pool.Client.RestartContainer(t.container.Container.ID, 30)
+	if err != nil {
+		return fmt.Errorf("failed to restart container %s: %w", t.hostname, err)
+	}
+
+	// Wait for the container to be back up and tailscaled to be ready
+	// We use exponential backoff to poll until we can successfully execute a command
+	_, err = backoff.Retry(context.Background(), func() (struct{}, error) {
+		// Try to execute a simple command to verify the container is responsive
+		_, _, err := t.Execute([]string{"tailscale", "version"}, dockertestutil.ExecuteCommandTimeout(5*time.Second))
+		if err != nil {
+			return struct{}{}, fmt.Errorf("container not ready: %w", err)
+		}
+		return struct{}{}, nil
+	}, backoff.WithBackOff(backoff.NewExponentialBackOff()), backoff.WithMaxElapsedTime(30*time.Second))
+
+	if err != nil {
+		return fmt.Errorf("timeout waiting for container %s to restart and become ready: %w", t.hostname, err)
+	}
+
+	return nil
+}
+
 // Helper that runs `tailscale up` with no arguments.
 func (t *TailscaleInContainer) Up() error {
 	command := []string{

mkdocs.yml

@@ -104,7 +104,7 @@ extra:
     - icon: fontawesome/brands/discord
       link: https://discord.gg/c84AZQhmpx
   headscale:
-    version: 0.27.0
+    version: 0.27.1
 
 # Extensions
 markdown_extensions: