diff --git a/desktop/flipper-server-core/src/FlipperServerImpl.tsx b/desktop/flipper-server-core/src/FlipperServerImpl.tsx
index 43eccbcd8..616098144 100644
--- a/desktop/flipper-server-core/src/FlipperServerImpl.tsx
+++ b/desktop/flipper-server-core/src/FlipperServerImpl.tsx
@@ -8,7 +8,7 @@
  */
 
 import EventEmitter from 'events';
-import ServerController from './comms/ServerController';
+import {ServerController} from './comms/ServerController';
 import {CertificateExchangeMedium} from './utils/CertificateProvider';
 import {AndroidDeviceManager} from './devices/android/androidDeviceManager';
 import {IOSDeviceManager} from './devices/ios/iOSDeviceManager';
diff --git a/desktop/flipper-server-core/src/comms/ServerAdapter.tsx b/desktop/flipper-server-core/src/comms/ServerAdapter.tsx
index 57892896e..2192d5a75 100644
--- a/desktop/flipper-server-core/src/comms/ServerAdapter.tsx
+++ b/desktop/flipper-server-core/src/comms/ServerAdapter.tsx
@@ -105,6 +105,8 @@ export interface ServerEventsListener {
    * // TODO: payload should become JSON
    */
   onClientMessage(clientId: string, payload: string): void;
+
+  onClientSetupError(clientQuery: ClientQuery, error: any): void;
 }
 
 /**
@@ -178,12 +180,7 @@ abstract class ServerAdapter {
         });
         return response;
       } catch (e) {
-        console.warn(
-          `[conn] Failed to exchange certificate with ${clientQuery.app} on ${
-            clientQuery.device || clientQuery.device_id
-          }`,
-          e,
-        );
+        this.listener.onClientSetupError(clientQuery, e);
       }
     }
 
diff --git a/desktop/flipper-server-core/src/comms/ServerController.tsx b/desktop/flipper-server-core/src/comms/ServerController.tsx
index 7db2a9cfe..3368b9ec6 100644
--- a/desktop/flipper-server-core/src/comms/ServerController.tsx
+++ b/desktop/flipper-server-core/src/comms/ServerController.tsx
@@ -64,10 +64,6 @@ type ClientCsrQuery = {
   csr_path?: string | undefined;
 };
 
-interface ServerController {
-  on(event: 'error', callback: (err: Error) => void): this;
-}
-
 /**
  * Responsible of creating and managing the actual underlying servers:
  * - Insecure (used for certificate exchange)
@@ -76,7 +72,10 @@ interface ServerController {
  *
  * Additionally, it manages client connections.
  */
-class ServerController extends EventEmitter implements ServerEventsListener {
+export class ServerController
+  extends EventEmitter
+  implements ServerEventsListener
+{
   connections: Map<string, ClientInfo> = new Map();
   timestamps: Map<string, ClientTimestampTracker> = new Map();
 
@@ -168,7 +167,7 @@ class ServerController extends EventEmitter implements ServerEventsListener {
   onConnectionCreated(
     clientQuery: SecureClientQuery,
     clientConnection: ClientConnection,
-    downgrade: boolean,
+    downgrade?: boolean,
   ): Promise<ClientDescription> {
     const {app, os, device, device_id, sdk_version, csr, csr_path, medium} =
       clientQuery;
@@ -361,6 +360,26 @@ class ServerController extends EventEmitter implements ServerEventsListener {
     return null;
   }
 
+  onClientSetupError(clientQuery: ClientQuery, e: any) {
+    console.warn(
+      `[conn] Failed to exchange certificate with ${clientQuery.app} on ${
+        clientQuery.device || clientQuery.device_id
+      }`,
+      e,
+    );
+    const client: UninitializedClient = {
+      os: clientQuery.os,
+      deviceName: clientQuery.device,
+      appName: appNameWithUpdateHint(clientQuery),
+    };
+    this.emit('client-setup-error', {
+      client,
+      error: `[conn] Failed to exchange certificate with ${
+        clientQuery.app
+      } on ${clientQuery.device || clientQuery.device_id}: ${e}`,
+    });
+  }
+
   /**
    * Creates a Client and sets the underlying connection.
    * @param connection A client connection to communicate between server and client.
@@ -527,8 +546,6 @@ class ConnectionTracker {
   }
 }
 
-export default ServerController;
-
 function clientQueryToKey(clientQuery: ClientQuery): string {
   return `${clientQuery.app}/${clientQuery.os}/${clientQuery.device}/${clientQuery.device_id}`;
 }
diff --git a/desktop/flipper-server-core/src/comms/__tests__/utils.tsx b/desktop/flipper-server-core/src/comms/__tests__/utils.tsx
index bb97b5fee..864bab419 100644
--- a/desktop/flipper-server-core/src/comms/__tests__/utils.tsx
+++ b/desktop/flipper-server-core/src/comms/__tests__/utils.tsx
@@ -62,4 +62,5 @@ export const createMockSEListener = (): ServerEventsListener => ({
   onConnectionClosed: jest.fn(),
   onError: jest.fn(),
   onClientMessage: jest.fn(),
+  onClientSetupError: jest.fn(),
 });
diff --git a/desktop/flipper-server-core/src/devices/ios/iOSContainerUtility.tsx b/desktop/flipper-server-core/src/devices/ios/iOSContainerUtility.tsx
index b77b09608..c4fd8a1c6 100644
--- a/desktop/flipper-server-core/src/devices/ios/iOSContainerUtility.tsx
+++ b/desktop/flipper-server-core/src/devices/ios/iOSContainerUtility.tsx
@@ -210,17 +210,15 @@ async function push(
 ): Promise<void> {
   await memoize(checkIdbIsInstalled)(idbPath);
 
-  return wrapWithErrorMessage(
-    reportPlatformFailures(
-      safeExec(
-        `${idbPath} file push --log ${idbLogLevel} --udid ${udid} --bundle-id ${bundleId} '${src}' '${dst}'`,
-      )
-        .then(() => {
-          return;
-        })
-        .catch((e) => handleMissingIdb(e, idbPath)),
-      `${operationPrefix}:push`,
-    ),
+  return reportPlatformFailures(
+    safeExec(
+      `${idbPath} file push --log ${idbLogLevel} --udid ${udid} --bundle-id ${bundleId} '${src}' '${dst}'`,
+    )
+      .then(() => {
+        return;
+      })
+      .catch((e) => handleMissingIdb(e, idbPath)),
+    `${operationPrefix}:push`,
   );
 }
 
@@ -233,18 +231,16 @@ async function pull(
 ): Promise<void> {
   await memoize(checkIdbIsInstalled)(idbPath);
 
-  return wrapWithErrorMessage(
-    reportPlatformFailures(
-      safeExec(
-        `${idbPath} file pull --log ${idbLogLevel} --udid ${udid} --bundle-id ${bundleId} '${src}' '${dst}'`,
-      )
-        .then(() => {
-          return;
-        })
-        .catch((e) => handleMissingIdb(e, idbPath))
-        .catch((e) => handleMissingPermissions(e)),
-      `${operationPrefix}:pull`,
-    ),
+  return reportPlatformFailures(
+    safeExec(
+      `${idbPath} file pull --log ${idbLogLevel} --udid ${udid} --bundle-id ${bundleId} '${src}' '${dst}'`,
+    )
+      .then(() => {
+        return;
+      })
+      .catch((e) => handleMissingIdb(e, idbPath))
+      .catch((e) => handleMissingPermissions(e)),
+    `${operationPrefix}:pull`,
   );
 }
 
@@ -282,23 +278,12 @@ function handleMissingPermissions(e: Error): void {
     console.warn(e);
     throw new Error(
       'Cannot connect to iOS application. idb_certificate_pull_failed' +
-        'Idb lacks permissions to exchange certificates. Did you install a source build ([FB] or enable certificate exchange)? ' +
-        e,
+        'Idb lacks permissions to exchange certificates. Did you install a source build ([FB] or enable certificate exchange)? See console logs for more details.',
     );
   }
   throw e;
 }
 
-function wrapWithErrorMessage<T>(p: Promise<T>): Promise<T> {
-  return p.catch((e: Error) => {
-    console.warn(e);
-    // Give the user instructions. Don't embed the error because it's unique per invocation so won't be deduped.
-    throw new Error(
-      "A problem with idb has ocurred. Please run `sudo rm -rf /tmp/idb*` and `sudo yum install -y fb-idb` to update it, if that doesn't fix it, post in Flipper Support.",
-    );
-  });
-}
-
 async function isXcodeDetected(): Promise<boolean> {
   return exec('xcode-select -p')
     .then(({stdout}) => {