diff --git a/apps/desktop/src/plugins/hermes-bots/relay.test.ts b/apps/desktop/src/plugins/hermes-bots/relay.test.ts
index ae14216422..9c98c2d509 100644
--- a/apps/desktop/src/plugins/hermes-bots/relay.test.ts
+++ b/apps/desktop/src/plugins/hermes-bots/relay.test.ts
@@ -740,4 +740,33 @@ describe('the roster loop forgets a machine that left', () => {
 
     stopBotRelay()
   })
+
+  it('clears the roster of a sole connection that replaced the previous sole one', async () => {
+    const calls = respondWith(call => {
+      if (call.method === 'profiles.list') {
+        return { profiles: [{ name: call.connectionId === 'a' ? 'default' : 'ops' }] }
+      }
+
+      return {}
+    })
+
+    const { startBotRelay, stopBotRelay } = await loadRelay()
+
+    startBotRelay()
+    await vi.advanceTimersByTimeAsync(0)
+    hostMock.profileRoutes = vi.fn(async () => [route('a')])
+    await vi.advanceTimersByTimeAsync(60_000)
+    calls.length = 0
+
+    // a is swapped for c between ticks — still one connection, but c's
+    // gateway has never been told the roster is empty.
+    hostMock.profileRoutes = vi.fn(async () => [route('c')])
+    await vi.advanceTimersByTimeAsync(60_000)
+
+    expect(calls.filter(call => call.method === 'bot_relay.roster.sync').map(call => call.connectionId)).toEqual([
+      'c'
+    ])
+
+    stopBotRelay()
+  })
 })
diff --git a/apps/desktop/src/plugins/hermes-bots/relay.ts b/apps/desktop/src/plugins/hermes-bots/relay.ts
index 046d450b47..75b34c4590 100644
--- a/apps/desktop/src/plugins/hermes-bots/relay.ts
+++ b/apps/desktop/src/plugins/hermes-bots/relay.ts
@@ -80,8 +80,8 @@ interface RelayLifecycle {
   pushDebounceTimer: null | ReturnType<typeof setTimeout>
   pushUnsub: (() => void) | null
   rosterBusy: boolean
-  /** The below-two-connections roster clear went out; stays set until the peer set relays again. */
-  rosterCleared: boolean
+  /** Id of the sole connection whose roster clear went out; null once the peer set relays again. */
+  rosterClearedFor: null | string
   rosterTimer: null | ReturnType<typeof setInterval>
 }
 
@@ -93,7 +93,7 @@ const relay: RelayLifecycle = {
   pushDebounceTimer: null,
   pushUnsub: null,
   rosterBusy: false,
-  rosterCleared: false,
+  rosterClearedFor: null,
   rosterTimer: null
 }
 
@@ -264,10 +264,11 @@ async function syncRelayRosters() {
       // Nothing to relay — but the gateways that remain still hold the last
       // pushed roster, so a departed machine's agents would stay in every
       // bot's prompt (and as message_agent targets) until a second connection
-      // reappears. Push the now-empty roster once so they forget it. An empty
-      // route list (registry not loaded yet) must not spend the one clear.
-      if (connections.length === 1 && !relay.rosterCleared) {
-        relay.rosterCleared = true
+      // reappears. Push the now-empty roster once per sole connection so it
+      // forgets it — a replacement sole connection has never been told. An
+      // empty route list (registry not loaded yet) must not spend the clear.
+      if (connections.length === 1 && connections[0].id !== relay.rosterClearedFor) {
+        relay.rosterClearedFor = connections[0].id
         await Promise.all(
           connections.map(async connection => {
             try {
@@ -282,7 +283,7 @@ async function syncRelayRosters() {
       return
     }
 
-    relay.rosterCleared = false
+    relay.rosterClearedFor = null
 
     const agentsByConnection = new Map<string, RelayAgentRow[]>()
     await Promise.all(
@@ -486,7 +487,7 @@ function scheduleRelayPushDrain() {
 
 export function startBotRelay() {
   relay.disposed = false
-  relay.rosterCleared = false
+  relay.rosterClearedFor = null
 
   // Source-shape test harnesses evaluate plugin.js without DOM timers —
   // the relay only runs where a real event loop exists.