diff --git a/libsignal-service/src/main/java/org/whispersystems/signalservice/api/username/UsernameApi.kt b/libsignal-service/src/main/java/org/whispersystems/signalservice/api/username/UsernameApi.kt
index 070a20ad14..942b3bd281 100644
--- a/libsignal-service/src/main/java/org/whispersystems/signalservice/api/username/UsernameApi.kt
+++ b/libsignal-service/src/main/java/org/whispersystems/signalservice/api/username/UsernameApi.kt
@@ -31,7 +31,7 @@ class UsernameApi(private val unauthWebSocket: SignalWebSocket.UnauthenticatedWe
    */
   fun getAciByUsername(username: Username): RequestResult<ServiceId.ACI?, Nothing> {
     return runBlocking {
-      unauthWebSocket.runWithUnauthChatConnection { chatConnection ->
+      unauthWebSocket.runCatchingWithUnauthChatConnection { chatConnection ->
         UnauthUsernamesService(chatConnection).lookUpUsernameHash(username.hash)
       }.getOrError().map { it?.let { ServiceId.ACI.fromLibSignal(it) } }
     }
diff --git a/libsignal-service/src/main/java/org/whispersystems/signalservice/api/websocket/SignalWebSocket.kt b/libsignal-service/src/main/java/org/whispersystems/signalservice/api/websocket/SignalWebSocket.kt
index 55044aa280..d88b9ce2dd 100644
--- a/libsignal-service/src/main/java/org/whispersystems/signalservice/api/websocket/SignalWebSocket.kt
+++ b/libsignal-service/src/main/java/org/whispersystems/signalservice/api/websocket/SignalWebSocket.kt
@@ -14,7 +14,10 @@ import io.reactivex.rxjava3.schedulers.Schedulers
 import io.reactivex.rxjava3.subjects.BehaviorSubject
 import org.signal.core.util.logging.Log
 import org.signal.core.util.orNull
-import org.signal.libsignal.net.ChatConnection
+import org.signal.libsignal.internal.CompletableFuture
+import org.signal.libsignal.net.BadRequestError
+import org.signal.libsignal.net.RequestResult
+import org.signal.libsignal.net.UnauthenticatedChatConnection
 import org.whispersystems.signalservice.api.crypto.SealedSenderAccess
 import org.whispersystems.signalservice.api.messages.EnvelopeResponse
 import org.whispersystems.signalservice.api.util.SleepTimer
@@ -24,6 +27,8 @@ import org.whispersystems.signalservice.internal.websocket.WebSocketRequestMessa
 import org.whispersystems.signalservice.internal.websocket.WebSocketResponseMessage
 import org.whispersystems.signalservice.internal.websocket.WebsocketResponse
 import java.io.IOException
+import java.util.concurrent.CancellationException
+import java.util.concurrent.CompletionException
 import java.util.concurrent.CopyOnWriteArraySet
 import java.util.concurrent.TimeoutException
 import kotlin.time.Duration
@@ -325,8 +330,26 @@ sealed class SignalWebSocket(
       }
     }
 
-    suspend fun <T> runWithUnauthChatConnection(callback: (org.signal.libsignal.net.UnauthenticatedChatConnection) -> T): T {
-      return getWebSocket().runWithChatConnection(callback as (ChatConnection) -> T)
+    suspend fun <Result, Error : BadRequestError> runCatchingWithUnauthChatConnection(
+      callback: (UnauthenticatedChatConnection) -> CompletableFuture<RequestResult<Result, Error>>
+    ): CompletableFuture<RequestResult<Result, Error>> {
+      val requestFuture = try {
+        getWebSocket().runWithChatConnection { chatConnection ->
+          val unauthenticatedConnection = chatConnection as? UnauthenticatedChatConnection
+            ?: throw IllegalStateException("Expected unauthenticated chat connection but got ${chatConnection::class.java.simpleName}")
+          callback(unauthenticatedConnection)
+        }
+      } catch (throwable: Throwable) {
+        return CompletableFuture.completedFuture(throwable.toNetworkRequestResult())
+      }
+
+      return requestFuture.handle { result, throwable ->
+        when {
+          throwable != null -> throwable.toNetworkRequestResult()
+          result != null -> result
+          else -> RequestResult.ApplicationError(IllegalStateException("RequestResult was null"))
+        }
+      }
     }
   }
 
@@ -447,3 +470,16 @@ sealed class SignalWebSocket(
     fun canConnect(): Boolean
   }
 }
+
+private fun <T, E : BadRequestError> Throwable.toNetworkRequestResult(): RequestResult<T, E> {
+  val cause = if (this is CompletionException && this.cause != null) {
+    this.cause!!
+  } else {
+    this
+  }
+  return when (cause) {
+    is IOException -> RequestResult.RetryableNetworkError(cause)
+    is CancellationException -> RequestResult.RetryableNetworkError(IOException("Request cancelled", cause))
+    else -> RequestResult.ApplicationError(cause)
+  }
+}