diff --git a/packages/app/src/runtime/host-runtime.test.ts b/packages/app/src/runtime/host-runtime.test.ts
index 0bf60240e0..d622f7ebef 100644
--- a/packages/app/src/runtime/host-runtime.test.ts
+++ b/packages/app/src/runtime/host-runtime.test.ts
@@ -56,6 +56,7 @@ class FakeDaemonClient {
   supportsBackgroundWorkspaces(): boolean {
     return false;
   }
+  relaySecurityFloor: "legacy" | "protected" | undefined = undefined;
   private state: ConnectionState = { status: "idle" };
   private listeners = new Set<(status: ConnectionState) => void>();
   private error: string | null = null;
@@ -813,6 +814,8 @@ describe("HostRuntimeController", () => {
     });
 
     await controller.activateConnection({ connectionId: relay.id });
+    // The client negotiated protected itself; the pin it reported is already enforced.
+    createdClients[0]!.relaySecurityFloor = "protected";
     await controller.updateHost(
       makeHost({
         connections: [{ ...relay, minimumSecurityMode: "protected" }],
@@ -825,6 +828,44 @@ describe("HostRuntimeController", () => {
     expect(controller.getSnapshot().client).toBe(createdClients[0]);
   });
 
+  it("replaces the active legacy relay client when a strict offer pins its connection", async () => {
+    const relay: HostConnection = {
+      id: "relay:wss:relay.paseo.sh:443",
+      type: "relay",
+      relayEndpoint: "relay.paseo.sh:443",
+      useTls: true,
+      daemonPublicKeyB64: "pk_a",
+    };
+    const createdClients: Array<{ client: FakeDaemonClient; connection: HostConnection }> = [];
+    const controller = new HostRuntimeController({
+      host: makeHost({ connections: [relay], preferredConnectionId: relay.id }),
+      deps: {
+        createClient: ({ connection }) => {
+          const client = new FakeDaemonClient();
+          createdClients.push({ client, connection });
+          return client as unknown as DaemonClient;
+        },
+        connectToDaemon: async ({ host, connection }) => ({
+          client: makeConnectedProbeClient(5) as unknown as DaemonClient,
+          serverId: host.serverId,
+          hostname: connection.id,
+        }),
+        getClientId: async () => "cid_test_runtime",
+      },
+    });
+
+    await controller.activateConnection({ connectionId: relay.id });
+    expect(createdClients[0]?.client.relaySecurityFloor).toBeUndefined();
+    const pinned: HostConnection = { ...relay, minimumSecurityMode: "protected" };
+    await controller.updateHost(
+      makeHost({ connections: [pinned], preferredConnectionId: relay.id }),
+    );
+
+    expect(createdClients.map((entry) => entry.connection)).toEqual([relay, pinned]);
+    expect(createdClients[0]?.client.isDisposed()).toBe(true);
+    expect(controller.getSnapshot().client).toBe(createdClients[1]?.client);
+  });
+
   it("keeps known hosts in connecting when a created client reports idle during connect", async () => {
     const host = makeHost({
       connections: [
diff --git a/packages/app/src/runtime/host-runtime.ts b/packages/app/src/runtime/host-runtime.ts
index eb7af2053c..63dacb0b1e 100644
--- a/packages/app/src/runtime/host-runtime.ts
+++ b/packages/app/src/runtime/host-runtime.ts
@@ -505,14 +505,24 @@ function buildConnectionCandidates(host: HostProfile): ConnectionCandidate[] {
 }
 
 /**
- * A security pin is learned from the client that is already connected in
- * protected mode, so tightening it never requires a new client.
+ * A pin learned from the active client is already enforced by that client, so
+ * it keeps running. A pin that arrived from elsewhere (a strict offer) while
+ * the active client is still legacy needs a client that enforces it.
  */
-function connectionNeedsNewClient(previous: HostConnection, next: HostConnection): boolean {
+function connectionNeedsNewClient(
+  previous: HostConnection,
+  next: HostConnection,
+  activeClient: DaemonClient | null,
+): boolean {
   if (previous.type === "relay" && next.type === "relay") {
-    const { minimumSecurityMode: _previousPin, ...previousRest } = previous;
-    const { minimumSecurityMode: _nextPin, ...nextRest } = next;
-    return !equal(previousRest, nextRest);
+    const { minimumSecurityMode: previousPin, ...previousRest } = previous;
+    const { minimumSecurityMode: nextPin, ...nextRest } = next;
+    if (!equal(previousRest, nextRest)) return true;
+    return (
+      nextPin === "protected" &&
+      previousPin !== "protected" &&
+      activeClient?.relaySecurityFloor !== "protected"
+    );
   }
   return !equal(previous, next);
 }
@@ -835,7 +845,12 @@ export class HostRuntimeController {
       activeConnectionId &&
       previousActiveConnection &&
       nextActiveConnection &&
-      (connectionNeedsNewClient(previousActiveConnection, nextActiveConnection) || passwordChanged)
+      (connectionNeedsNewClient(
+        previousActiveConnection,
+        nextActiveConnection,
+        this.activeClient,
+      ) ||
+        passwordChanged)
     ) {
       this.connectionLastProbedAt.delete(activeConnectionId);
       await this.switchToConnection({ connectionId: activeConnectionId });
diff --git a/packages/app/src/types/host-connection.test.ts b/packages/app/src/types/host-connection.test.ts
index 3e33f62f1a..8d7fb87b35 100644
--- a/packages/app/src/types/host-connection.test.ts
+++ b/packages/app/src/types/host-connection.test.ts
@@ -361,6 +361,38 @@ describe("relay endpoint security pin", () => {
     expect(profiles[0].connections).toEqual([pinned]);
   });
 
+  it("is persisted when a strict offer re-imports an unpinned route", () => {
+    const profiles = [
+      { ...makeHost("srv"), connections: [unpinned], preferredConnectionId: unpinned.id },
+    ];
+    const next = upsertHostConnectionInProfiles({
+      profiles,
+      serverId: "srv",
+      connection: pinned,
+    });
+    expect(next).not.toBe(profiles);
+    expect(next[0].connections).toEqual([pinned]);
+  });
+
+  it("tightens every route to the same daemon identity when a strict offer arrives through another relay", () => {
+    const strictElsewhere: HostConnection = {
+      id: "relay:wss:other.example.com:443",
+      type: "relay",
+      relayEndpoint: "other.example.com:443",
+      useTls: true,
+      daemonPublicKeyB64: "pk_a",
+      minimumSecurityMode: "protected",
+    };
+    const profiles = upsertHostConnectionInProfiles({
+      profiles: [
+        { ...makeHost("srv"), connections: [unpinned], preferredConnectionId: unpinned.id },
+      ],
+      serverId: "srv",
+      connection: strictElsewhere,
+    });
+    expect(profiles[0].connections).toEqual([pinned, strictElsewhere]);
+  });
+
   it("follows the daemon identity to a relay at another address", () => {
     const elsewhere: HostConnection = {
       id: "relay:wss:other.example.com:443",
diff --git a/packages/app/src/types/host-connection.ts b/packages/app/src/types/host-connection.ts
index 8b2bcea3fe..e7449b9a67 100644
--- a/packages/app/src/types/host-connection.ts
+++ b/packages/app/src/types/host-connection.ts
@@ -185,7 +185,6 @@ function upsertHostConnectionById(
   connections: HostConnection[],
   connection: HostConnection,
 ): HostConnection[] {
-  const incoming = keepRelaySecurityPin(connections, connection);
   const next: HostConnection[] = [];
   let replaced = false;
   for (const existing of connections) {
@@ -195,29 +194,42 @@ function upsertHostConnectionById(
     }
 
     if (replaced) continue;
-    next.push(incoming);
+    next.push(connection);
     replaced = true;
   }
-  if (!replaced) next.push(incoming);
-  return next;
+  if (!replaced) next.push(connection);
+  // A pin is never lost: the replaced record counts as much as the incoming one.
+  return shareRelaySecurityPin(next, [...connections, connection]);
 }
 
 /**
- * The security pin belongs to the daemon identity, not to one relay address:
- * a re-import of a pinned key keeps the pin, through any relay.
+ * The security pin belongs to the daemon identity, not to one relay address.
+ * Once any relay route to a key is pinned, by a strict offer or a learned
+ * handshake, every route to that key is pinned.
  */
-function keepRelaySecurityPin(
+function shareRelaySecurityPin(
   connections: HostConnection[],
-  incoming: HostConnection,
-): HostConnection {
-  if (incoming.type !== "relay" || incoming.minimumSecurityMode === "protected") return incoming;
-  const pinned = connections.some(
-    (connection) =>
-      connection.type === "relay" &&
-      connection.minimumSecurityMode === "protected" &&
-      connection.daemonPublicKeyB64 === incoming.daemonPublicKeyB64,
+  pinSources: HostConnection[],
+): HostConnection[] {
+  const pinnedKeys = new Set<string>();
+  for (const connection of pinSources) {
+    if (connection.type === "relay" && connection.minimumSecurityMode === "protected") {
+      pinnedKeys.add(connection.daemonPublicKeyB64);
+    }
+  }
+  return connections.map((connection) =>
+    connection.type === "relay" &&
+    connection.minimumSecurityMode !== "protected" &&
+    pinnedKeys.has(connection.daemonPublicKeyB64)
+      ? { ...connection, minimumSecurityMode: "protected" as const }
+      : connection,
   );
-  return pinned ? { ...incoming, minimumSecurityMode: "protected" } : incoming;
+}
+
+function relaySecurityPinEquals(left: HostConnection, right: HostConnection): boolean {
+  const pinOf = (connection: HostConnection) =>
+    connection.type === "relay" ? connection.minimumSecurityMode : undefined;
+  return pinOf(left) === pinOf(right);
 }
 
 /**
@@ -274,7 +286,10 @@ function hasProfileChanged(input: {
     connections.length !== previous.connections.length ||
     connections.some((candidate, index) => {
       const old = previous.connections[index];
-      return !old || !hostConnectionEquals(candidate, old);
+      // Identity equality decides profile matching; the pin is policy on top of it.
+      return (
+        !old || !hostConnectionEquals(candidate, old) || !relaySecurityPinEquals(candidate, old)
+      );
     })
   );
 }
diff --git a/packages/client/src/daemon-client.ts b/packages/client/src/daemon-client.ts
index ca8fc2476a..3b0e0718a2 100644
--- a/packages/client/src/daemon-client.ts
+++ b/packages/client/src/daemon-client.ts
@@ -1345,7 +1345,7 @@ export class DaemonClient {
    * Starts at the configured minimum and rises to "protected" once a daemon
    * negotiates it, so a later reconnect cannot be downgraded to legacy.
    */
-  private relaySecurityFloor: RelaySecurityMode | undefined;
+  private relaySecurityFloorValue: RelaySecurityMode | undefined;
   private readonly logConnectionPath: "direct" | "relay";
   private readonly logServerId: string | null;
   private readonly logClientIdHash: string;
@@ -1361,7 +1361,7 @@ export class DaemonClient {
 
   constructor(private config: DaemonClientConfig) {
     this.logger = config.logger ?? consoleLogger;
-    this.relaySecurityFloor = config.e2ee?.minimumMode;
+    this.relaySecurityFloorValue = config.e2ee?.minimumMode;
     this.logConnectionPath = isRelayClientWebSocketUrl(this.config.url) ? "relay" : "direct";
     let parsedUrlForLog: URL | null = null;
     try {
@@ -1479,9 +1479,9 @@ export class DaemonClient {
           baseFactory: transportFactory,
           daemonPublicKeyB64,
           logger: this.logger,
-          ...(this.relaySecurityFloor ? { minimumMode: this.relaySecurityFloor } : {}),
+          ...(this.relaySecurityFloorValue ? { minimumMode: this.relaySecurityFloorValue } : {}),
           onSecurityMode: (mode) => {
-            if (mode === "protected") this.relaySecurityFloor = "protected";
+            if (mode === "protected") this.relaySecurityFloorValue = "protected";
             this.config.e2ee?.onSecurityMode?.(mode);
           },
         });
@@ -1848,6 +1848,11 @@ export class DaemonClient {
     return this.connectionState.status === "connecting";
   }
 
+  /** The relay endpoint security this client requires on its next attempt. */
+  get relaySecurityFloor(): RelaySecurityMode | undefined {
+    return this.relaySecurityFloorValue;
+  }
+
   get lastError(): string | null {
     return this.lastErrorValue;
   }