diff --git a/app/src/main/java/org/thoughtcrime/securesms/messages/GroupSendUtil.java b/app/src/main/java/org/thoughtcrime/securesms/messages/GroupSendUtil.java
index 7342c78ca1..63347c01f1 100644
--- a/app/src/main/java/org/thoughtcrime/securesms/messages/GroupSendUtil.java
+++ b/app/src/main/java/org/thoughtcrime/securesms/messages/GroupSendUtil.java
@@ -638,13 +638,17 @@ public final class GroupSendUtil {
         SealedSenderAccess sealedSenderAccess = sealedSenderAccesses.get(0);
         SendMessageResult  result;
 
-        if (editMessage != null) {
-          result = messageSender.sendEditMessage(targets.get(0), sealedSenderAccess, contentHint, message, SignalServiceMessageSender.IndividualSendEvents.EMPTY, urgent, editMessage.getTargetSentTimestamp());
-        } else {
-          result = messageSender.sendDataMessage(targets.get(0), sealedSenderAccess, contentHint, message, SignalServiceMessageSender.IndividualSendEvents.EMPTY, urgent, targetRecipient.getNeedsPniSignature());
+        try {
+          if (editMessage != null) {
+            result = messageSender.sendEditMessage(targets.get(0), sealedSenderAccess, contentHint, message, SignalServiceMessageSender.IndividualSendEvents.EMPTY, urgent, editMessage.getTargetSentTimestamp());
+          } else {
+            result = messageSender.sendDataMessage(targets.get(0), sealedSenderAccess, contentHint, message, SignalServiceMessageSender.IndividualSendEvents.EMPTY, urgent, targetRecipient.getNeedsPniSignature());
+          }
+        } catch (IOException e) {
+          result = SignalServiceMessageSender.mapSendErrorToSendResult(e, message.getTimestamp(), targets.get(0));
         }
 
-        if (targetRecipient.getNeedsPniSignature()) {
+        if (result.isSuccess() && targetRecipient.getNeedsPniSignature()) {
           SignalDatabase.pendingPniSignatureMessages().insertIfNecessary(targetRecipients.get(0).getId(), getSentTimestamp(), result);
         }
 
diff --git a/libsignal-service/src/main/java/org/whispersystems/signalservice/api/SignalServiceMessageSender.java b/libsignal-service/src/main/java/org/whispersystems/signalservice/api/SignalServiceMessageSender.java
index fffcfe831e..cb05d76330 100644
--- a/libsignal-service/src/main/java/org/whispersystems/signalservice/api/SignalServiceMessageSender.java
+++ b/libsignal-service/src/main/java/org/whispersystems/signalservice/api/SignalServiceMessageSender.java
@@ -6,7 +6,6 @@
 package org.whispersystems.signalservice.api;
 
 import org.signal.core.util.Base64;
-import org.signal.libsignal.metadata.certificate.SenderCertificate;
 import org.signal.libsignal.protocol.IdentityKey;
 import org.signal.libsignal.protocol.IdentityKeyPair;
 import org.signal.libsignal.protocol.InvalidKeyException;
@@ -72,7 +71,6 @@ import org.whispersystems.signalservice.api.push.ServiceId;
 import org.whispersystems.signalservice.api.push.ServiceId.PNI;
 import org.whispersystems.signalservice.api.push.SignalServiceAddress;
 import org.whispersystems.signalservice.api.push.exceptions.AuthorizationFailedException;
-import org.whispersystems.signalservice.api.push.exceptions.MalformedResponseException;
 import org.whispersystems.signalservice.api.push.exceptions.NonSuccessfulResponseCodeException;
 import org.whispersystems.signalservice.api.push.exceptions.NotFoundException;
 import org.whispersystems.signalservice.api.push.exceptions.ProofRequiredException;
@@ -95,7 +93,6 @@ import org.whispersystems.signalservice.internal.crypto.AttachmentDigest;
 import org.whispersystems.signalservice.internal.crypto.PaddingInputStream;
 import org.whispersystems.signalservice.internal.push.AttachmentPointer;
 import org.whispersystems.signalservice.internal.push.AttachmentUploadForm;
-import org.whispersystems.signalservice.internal.push.AttachmentV2UploadAttributes;
 import org.whispersystems.signalservice.internal.push.BodyRange;
 import org.whispersystems.signalservice.internal.push.CallMessage;
 import org.whispersystems.signalservice.internal.push.Content;
@@ -2258,34 +2255,48 @@ public class SignalServiceMessageSender {
 
       return Single.error(t);
     }).onErrorResumeNext(t -> {
-      if (t instanceof UntrustedIdentityException) {
-        Log.w(TAG, "[" + timestamp + "] Hit identity mismatch: " + recipient.getIdentifier(), t);
-        return Single.just(SendMessageResult.identityFailure(recipient, ((UntrustedIdentityException) t).getIdentityKey()));
-      } else if (t instanceof UnregisteredUserException) {
-        Log.w(TAG, "[" + timestamp + "] Hit unregistered user: " + recipient.getIdentifier());
-        return Single.just(SendMessageResult.unregisteredFailure(recipient));
-      } else if (t instanceof PushNetworkException) {
-        Log.w(TAG, "[" + timestamp + "] Hit network failure: " + recipient.getIdentifier(), t);
-        return Single.just(SendMessageResult.networkFailure(recipient));
-      } else if (t instanceof ServerRejectedException) {
-        Log.w(TAG, "[" + timestamp + "] Hit server rejection: " + recipient.getIdentifier(), t);
-        return Single.error(t);
-      } else if (t instanceof ProofRequiredException) {
-        Log.w(TAG, "[" + timestamp + "] Hit proof required: " + recipient.getIdentifier(), t);
-        return Single.just(SendMessageResult.proofRequiredFailure(recipient, (ProofRequiredException) t));
-      } else if (t instanceof RateLimitException) {
-        Log.w(TAG, "[" + timestamp + "] Hit rate limit: " + recipient.getIdentifier(), t);
-        return Single.just(SendMessageResult.rateLimitFailure(recipient, (RateLimitException) t));
-      } else if (t instanceof InvalidPreKeyException) {
-        Log.w(TAG, "[" + timestamp + "] Hit invalid prekey: " + recipient.getIdentifier(), t);
-        return Single.just(SendMessageResult.invalidPreKeyFailure(recipient));
-      } else {
-        Log.w(TAG, "[" + timestamp + "] Hit unknown exception: " + recipient.getIdentifier(), t);
-        return Single.error(new IOException(t));
+      try {
+        SendMessageResult result = mapSendErrorToSendResult(t, timestamp, recipient);
+        return Single.just(result);
+      } catch (IOException e) {
+        return Single.error(e);
       }
     });
   }
 
+  /**
+   * Converts common exceptions thrown during message sending to the appropriate {@link SendMessageResult}.
+   * <p>
+   * Exceptions that cannot be mapped will be rethrown as wrapped {@link IOException}s.
+   */
+  public static @Nonnull SendMessageResult mapSendErrorToSendResult(@Nonnull Throwable t, long timestamp, @Nonnull SignalServiceAddress recipient) throws IOException {
+    if (t instanceof UntrustedIdentityException) {
+      Log.w(TAG, "[" + timestamp + "] Hit identity mismatch: " + recipient.getIdentifier(), t);
+      return SendMessageResult.identityFailure(recipient, ((UntrustedIdentityException) t).getIdentityKey());
+    } else if (t instanceof UnregisteredUserException) {
+      Log.w(TAG, "[" + timestamp + "] Hit unregistered user: " + recipient.getIdentifier());
+      return SendMessageResult.unregisteredFailure(recipient);
+    } else if (t instanceof PushNetworkException) {
+      Log.w(TAG, "[" + timestamp + "] Hit network failure: " + recipient.getIdentifier(), t);
+      return SendMessageResult.networkFailure(recipient);
+    } else if (t instanceof ServerRejectedException) {
+      Log.w(TAG, "[" + timestamp + "] Hit server rejection: " + recipient.getIdentifier(), t);
+      throw (ServerRejectedException) t;
+    } else if (t instanceof ProofRequiredException) {
+      Log.w(TAG, "[" + timestamp + "] Hit proof required: " + recipient.getIdentifier(), t);
+      return SendMessageResult.proofRequiredFailure(recipient, (ProofRequiredException) t);
+    } else if (t instanceof RateLimitException) {
+      Log.w(TAG, "[" + timestamp + "] Hit rate limit: " + recipient.getIdentifier(), t);
+      return SendMessageResult.rateLimitFailure(recipient, (RateLimitException) t);
+    } else if (t instanceof InvalidPreKeyException) {
+      Log.w(TAG, "[" + timestamp + "] Hit invalid prekey: " + recipient.getIdentifier(), t);
+      return SendMessageResult.invalidPreKeyFailure(recipient);
+    } else {
+      Log.w(TAG, "[" + timestamp + "] Hit unknown exception: " + recipient.getIdentifier(), t);
+      throw new IOException(t);
+    }
+  }
+
   /**
    * Will send a message using sender keys to all of the specified recipients. It is assumed that
    * all of the recipients have UUIDs.