diff --git a/.changeset/gentle-cloud-runtimes.md b/.changeset/gentle-cloud-runtimes.md
new file mode 100644
index 0000000000..417c6b0737
--- /dev/null
+++ b/.changeset/gentle-cloud-runtimes.md
@@ -0,0 +1,5 @@
+---
+"@electric-ax/agents-desktop": patch
+---
+
+Show a clear sign-in prompt when connecting an Electric Cloud server while signed out instead of surfacing pull-wake runner registration errors.
diff --git a/packages/agents-desktop/src/cloud/cloud-agent-servers.ts b/packages/agents-desktop/src/cloud/cloud-agent-servers.ts
index 4a98c9cf76..ead7741175 100644
--- a/packages/agents-desktop/src/cloud/cloud-agent-servers.ts
+++ b/packages/agents-desktop/src/cloud/cloud-agent-servers.ts
@@ -263,6 +263,9 @@ export class CloudAgentServers {
     if (!token) {
       throw new Error(`Not signed in to Electric Cloud`)
     }
+
+    const cached = this.getAgentsToken(tenantId)
+    if (cached) return { url, tenantId }
     const agentsToken = await this.fetchAgentsToken(tenantId, token)
     this.agentsTokens.set(tenantId, agentsToken)
     await this.secretStore.set(`${TOKEN_REF_PREFIX}${tenantId}`, agentsToken)
diff --git a/packages/agents-desktop/src/ipc/cloud.ts b/packages/agents-desktop/src/ipc/cloud.ts
index d91e313534..e54e4a915d 100644
--- a/packages/agents-desktop/src/ipc/cloud.ts
+++ b/packages/agents-desktop/src/ipc/cloud.ts
@@ -1,10 +1,15 @@
 import { BrowserWindow, ipcMain } from 'electron'
 import type { CloudAgentServers } from '../cloud/cloud-agent-servers'
 import type { CloudAuth, CloudAuthProvider } from '../cloud/cloud-auth'
+import type { ServerConfig } from '../shared/types'
 
 export type CloudIpcDeps = {
+  settings: {
+    servers: Array<ServerConfig>
+  }
   getCloudAuth: () => CloudAuth
   getCloudAgentServers: () => CloudAgentServers
+  forgetServer: (serverId: string) => Promise<void>
 }
 
 export function registerCloudIpcHandlers(deps: CloudIpcDeps): void {
@@ -20,6 +25,12 @@ export function registerCloudIpcHandlers(deps: CloudIpcDeps): void {
   )
   ipcMain.handle(`desktop:cloud-auth-sign-out`, async () => {
     await deps.getCloudAuth().signOut()
+    const cloudServerIds = deps.settings.servers
+      .filter((server) => server.source === `electric-cloud`)
+      .map((server) => server.id)
+    for (const serverId of cloudServerIds) {
+      await deps.forgetServer(serverId)
+    }
   })
   ipcMain.handle(`desktop:cloud-auth-open-dashboard`, () => {
     deps.getCloudAuth().openDashboard()
diff --git a/packages/agents-desktop/src/runtime/lifecycle.ts b/packages/agents-desktop/src/runtime/lifecycle.ts
index fdefba0c47..c3453af354 100644
--- a/packages/agents-desktop/src/runtime/lifecycle.ts
+++ b/packages/agents-desktop/src/runtime/lifecycle.ts
@@ -205,6 +205,15 @@ export async function startRuntime(
       deps.refreshDesktopState()
       return
     }
+
+    const cloudAuthState = deps.getCloudAuthState()
+    if (cloudAuthState?.status !== `signed-in`) {
+      entry.status = `error`
+      entry.lastError = `Sign in to Electric Cloud before connecting to ${activeServer.name}.`
+      deps.refreshDesktopState()
+      return
+    }
+
     try {
       const prepared = await deps
         .getCloudAgentServers()
@@ -214,18 +223,12 @@ export async function startRuntime(
         await deps.saveSettings()
       }
     } catch (err) {
-      const cachedToken = deps
-        .getCloudAgentServers()
-        .getAgentsToken(activeServer.tenantId)
-      if (!cachedToken) {
-        entry.status = `error`
-        entry.lastError = `Could not prepare cloud agents token for ${activeServer.name}: ${
-          err instanceof Error ? err.message : String(err)
-        }`
-        deps.refreshDesktopState()
-        return
-      }
-      console.warn(`[agents-desktop] cloud agents token refresh failed:`, err)
+      entry.status = `error`
+      entry.lastError = `Could not prepare cloud agents token for ${activeServer.name}: ${
+        err instanceof Error ? err.message : String(err)
+      }`
+      deps.refreshDesktopState()
+      return
     }
   }