diff --git a/app/routes/machines/components/machine-row.tsx b/app/routes/machines/components/machine-row.tsx
index d6bc4e52..0d764513 100644
--- a/app/routes/machines/components/machine-row.tsx
+++ b/app/routes/machines/components/machine-row.tsx
@@ -28,6 +28,7 @@ interface Props {
   isDisabled?: boolean;
   existingTags?: string[];
   supportsNodeOwnerChange: boolean;
+  supportsDisablingKeyExpiry: boolean;
 }
 
 export default function MachineRow({
@@ -38,6 +39,7 @@ export default function MachineRow({
   isDisabled,
   existingTags,
   supportsNodeOwnerChange,
+  supportsDisablingKeyExpiry,
 }: Props) {
   const uiTags = useMemo(() => uiTagsForNode(node, isAgent), [node, isAgent]);
 
@@ -144,6 +146,7 @@ export default function MachineRow({
           node={node}
           users={users}
           supportsNodeOwnerChange={supportsNodeOwnerChange}
+          supportsDisablingKeyExpiry={supportsDisablingKeyExpiry}
         />
       </td>
     </tr>
diff --git a/app/routes/machines/components/menu.tsx b/app/routes/machines/components/menu.tsx
index a0d2eaad..ba366f6c 100644
--- a/app/routes/machines/components/menu.tsx
+++ b/app/routes/machines/components/menu.tsx
@@ -1,11 +1,12 @@
 import { Cog, Ellipsis, SquareTerminal } from "lucide-react";
 import { useState } from "react";
+import { useSubmit } from "react-router";
 
 import Button from "~/components/button";
 import { Menu, MenuContent, MenuItem, MenuSeparator, MenuTrigger } from "~/components/menu";
 import type { User } from "~/types";
 import cn from "~/utils/cn";
-import { PopulatedNode } from "~/utils/node-info";
+import { isNoExpiry, type PopulatedNode } from "~/utils/node-info";
 
 import Delete from "../dialogs/delete";
 import Expire from "../dialogs/expire";
@@ -22,6 +23,7 @@ interface MenuProps {
   isDisabled?: boolean;
   existingTags?: string[];
   supportsNodeOwnerChange: boolean;
+  supportsDisablingKeyExpiry: boolean;
 }
 
 type Modal = "rename" | "expire" | "remove" | "routes" | "move" | "tags" | null;
@@ -34,7 +36,9 @@ export default function MachineMenu({
   isDisabled,
   existingTags,
   supportsNodeOwnerChange,
+  supportsDisablingKeyExpiry,
 }: MenuProps) {
+  const submit = useSubmit();
   const [modal, setModal] = useState<Modal>(null);
   const supportsTailscaleSSH = node.hostInfo?.sshHostKeys && node.hostInfo?.sshHostKeys.length > 0;
 
@@ -156,15 +160,33 @@ export default function MachineMenu({
         </MenuTrigger>
         <MenuContent>
           <MenuItem onClick={() => setModal("rename")}>Edit machine name</MenuItem>
+          {supportsDisablingKeyExpiry && (
+            <MenuItem
+              onClick={() =>
+                submit(
+                  {
+                    action_id: "toggle_expiry",
+                    node_id: node.id,
+                    disableExpiry: !isNoExpiry(node.expiry),
+                  },
+                  { method: "post" },
+                )
+              }
+            >
+              {isNoExpiry(node.expiry) ? "Enable" : "Disable"} key expiry
+            </MenuItem>
+          )}
           <MenuItem onClick={() => setModal("routes")}>Edit route settings</MenuItem>
           <MenuItem onClick={() => setModal("tags")}>Edit ACL tags</MenuItem>
           {supportsNodeOwnerChange && (
             <MenuItem onClick={() => setModal("move")}>Change owner</MenuItem>
           )}
           <MenuSeparator />
-          <MenuItem variant="danger" disabled={node.expired} onClick={() => setModal("expire")}>
-            Expire
-          </MenuItem>
+          {!isNoExpiry(node.expiry) && (
+            <MenuItem variant="danger" disabled={node.expired} onClick={() => setModal("expire")}>
+              Expire
+            </MenuItem>
+          )}
           <MenuItem variant="danger" onClick={() => setModal("remove")}>
             Remove
           </MenuItem>
diff --git a/app/routes/machines/machine-actions.ts b/app/routes/machines/machine-actions.ts
index fbb0a855..81d26643 100644
--- a/app/routes/machines/machine-actions.ts
+++ b/app/routes/machines/machine-actions.ts
@@ -113,6 +113,13 @@ export async function machineAction({ request, context }: Route.ActionArgs) {
       return { message: "Machine expired" };
     }
 
+    case "toggle_expiry": {
+      const disableExpiry = String(formData.get("disableExpiry")) === "true";
+      await api.nodes.toggleExpiry(nodeId, disableExpiry);
+      await headscaleLiveStore.refresh(nodesResource, api);
+      return { message: "Machine expired" };
+    }
+
     case "update_tags": {
       const tags = formData.get("tags")?.toString().split(",") ?? [];
       if (tags.length === 0) {
diff --git a/app/routes/machines/machine.tsx b/app/routes/machines/machine.tsx
index cca5412b..ffece95b 100644
--- a/app/routes/machines/machine.tsx
+++ b/app/routes/machines/machine.tsx
@@ -66,6 +66,7 @@ export async function loader({ request, params, context }: Route.LoaderArgs) {
   const [enhancedNode] = mapNodes([node], stats);
   const tags = [...node.tags].toSorted();
   const supportsNodeOwnerChange = !headscale.capabilities.nodeOwnerIsImmutable;
+  const supportsDisablingKeyExpiry = headscale.capabilities.keyExpiryCanBeDisabled;
   const agentSync = agents?.lastSync();
   const policy = policyResult.status === "fulfilled" ? policyResult.value.policy : undefined;
 
@@ -82,6 +83,7 @@ export async function loader({ request, params, context }: Route.LoaderArgs) {
     node: enhancedNode,
     stats: stats?.[enhancedNode.nodeKey],
     supportsNodeOwnerChange: supportsNodeOwnerChange,
+    supportsDisablingKeyExpiry: supportsDisablingKeyExpiry,
     tags,
     users,
   };
@@ -90,7 +92,17 @@ export async function loader({ request, params, context }: Route.LoaderArgs) {
 export const action = machineAction;
 
 export default function Page({
-  loaderData: { node, tags, users, magic, agent, stats, existingTags, supportsNodeOwnerChange },
+  loaderData: {
+    node,
+    tags,
+    users,
+    magic,
+    agent,
+    stats,
+    existingTags,
+    supportsNodeOwnerChange,
+    supportsDisablingKeyExpiry,
+  },
 }: Route.ComponentProps) {
   const [showRouting, setShowRouting] = useState(false);
 
@@ -125,6 +137,7 @@ export default function Page({
           node={node}
           users={users}
           supportsNodeOwnerChange={supportsNodeOwnerChange}
+          supportsDisablingKeyExpiry={supportsDisablingKeyExpiry}
         />
       </div>
       <div className="mb-4 flex gap-1">
diff --git a/app/routes/machines/overview.tsx b/app/routes/machines/overview.tsx
index 18d529b3..b082aa51 100644
--- a/app/routes/machines/overview.tsx
+++ b/app/routes/machines/overview.tsx
@@ -67,6 +67,7 @@ export async function loader({ request, context }: Route.LoaderArgs) {
   const policy = policyResult.status === "fulfilled" ? policyResult.value.policy : undefined;
   const populatedNodes = mapNodes(nodes, stats);
   const supportsNodeOwnerChange = !headscale.capabilities.nodeOwnerIsImmutable;
+  const supportsDisablingKeyExpiry = headscale.capabilities.keyExpiryCanBeDisabled;
   const agentSync = agents?.lastSync();
 
   return {
@@ -86,6 +87,7 @@ export async function loader({ request, context }: Route.LoaderArgs) {
     publicServer: config.headscale.public_url,
     server: config.headscale.url,
     supportsNodeOwnerChange: supportsNodeOwnerChange,
+    supportsDisablingKeyExpiry: supportsDisablingKeyExpiry,
     users,
     writable: writablePermission,
   };
@@ -458,6 +460,7 @@ export default function Page({ loaderData }: Route.ComponentProps) {
                   node={node}
                   users={loaderData.users}
                   supportsNodeOwnerChange={loaderData.supportsNodeOwnerChange}
+                  supportsDisablingKeyExpiry={loaderData.supportsDisablingKeyExpiry}
                 />
               ))
             )}
diff --git a/app/server/headscale/api/capabilities.ts b/app/server/headscale/api/capabilities.ts
index b3e98465..61c1e4a1 100644
--- a/app/server/headscale/api/capabilities.ts
+++ b/app/server/headscale/api/capabilities.ts
@@ -44,6 +44,11 @@ export interface Capabilities {
    * the `hskey-authreq-` prefix. Introduced in 0.29.0.
    */
   readonly registerKeyIncludesAuthReqPrefix: boolean;
+
+  /**
+   * Disabling of key expiry was introduced in 0.29.0.
+   */
+  readonly keyExpiryCanBeDisabled: boolean;
 }
 
 export function capabilitiesFor(version: ServerVersion): Capabilities {
@@ -52,5 +57,6 @@ export function capabilitiesFor(version: ServerVersion): Capabilities {
     nodeTagsAreFlat: gte(version, "0.28.0"),
     nodeOwnerIsImmutable: gte(version, "0.28.0"),
     registerKeyIncludesAuthReqPrefix: gte(version, "0.29.0"),
+    keyExpiryCanBeDisabled: gte(version, "0.29.0"),
   };
 }
diff --git a/app/server/headscale/api/resources/nodes.ts b/app/server/headscale/api/resources/nodes.ts
index 6fef30a8..d18b492c 100644
--- a/app/server/headscale/api/resources/nodes.ts
+++ b/app/server/headscale/api/resources/nodes.ts
@@ -19,6 +19,7 @@ export interface NodeApi {
   expire(id: string): Promise<void>;
   rename(id: string, newName: string): Promise<void>;
   setTags(id: string, tags: string[]): Promise<void>;
+  toggleExpiry(nodeId: string, disableExpiry: boolean): Promise<void>;
   /**
    * Reassign a node to a different user. Only present when
    * `capabilities.nodeOwnerIsImmutable` is false (Headscale < 0.28).
@@ -104,6 +105,13 @@ export function makeNodeApi(
         body: { tags },
       });
     },
+    toggleExpiry: async (nodeId, disableExpiry) => {
+      await transport.request({
+        method: "POST",
+        path: `v1/node/${nodeId}/expire?disableExpiry=${disableExpiry}`,
+        apiKey,
+      });
+    },
   };
 
   if (!capabilities.nodeOwnerIsImmutable) {
diff --git a/tests/integration/api/nodes.test.ts b/tests/integration/api/nodes.test.ts
index 27b4a3e8..57bfb353 100644
--- a/tests/integration/api/nodes.test.ts
+++ b/tests/integration/api/nodes.test.ts
@@ -111,6 +111,27 @@ describe.sequential.for(HS_VERSIONS)("Headscale %s: Users", (version) => {
     expect(expiredNode.expiry).toBeDefined();
   });
 
+  test("key expiry of nodes can be toggled", async (context) => {
+    const bootstrap = await getBootstrapClient(version);
+    // Key expiry was introduced in 0.29.0
+    if (!bootstrap.capabilities.keyExpiryCanBeDisabled) {
+      context.skip();
+    }
+
+    const client = await getRuntimeClient(version);
+    await client.nodes.toggleExpiry(workingNodeId, true);
+
+    const permanentNode = await client.nodes.get(workingNodeId);
+    expect(permanentNode).toBeDefined();
+    expect(permanentNode.expiry).toBeNull();
+
+    await client.nodes.toggleExpiry(workingNodeId, false);
+
+    const node = await client.nodes.get(workingNodeId);
+    expect(node).toBeDefined();
+    expect(node.expiry).not.toBeNull();
+  });
+
   test("nodes can be deleted", async () => {
     const client = await getRuntimeClient(version);
     await client.nodes.delete(workingNodeId);
diff --git a/tests/unit/headscale/server-version.test.ts b/tests/unit/headscale/server-version.test.ts
index 9aa5c760..a4c7289d 100644
--- a/tests/unit/headscale/server-version.test.ts
+++ b/tests/unit/headscale/server-version.test.ts
@@ -98,6 +98,7 @@ describe("capabilitiesFor", () => {
       nodeTagsAreFlat: true,
       nodeOwnerIsImmutable: true,
       registerKeyIncludesAuthReqPrefix: false,
+      keyExpiryCanBeDisabled: false,
     });
   });