diff --git a/app/src/main/java/org/thoughtcrime/securesms/jobs/AttachmentUploadJob.java b/app/src/main/java/org/thoughtcrime/securesms/jobs/AttachmentUploadJob.java
index 5b3bf0b34..ade4ad6ba 100644
--- a/app/src/main/java/org/thoughtcrime/securesms/jobs/AttachmentUploadJob.java
+++ b/app/src/main/java/org/thoughtcrime/securesms/jobs/AttachmentUploadJob.java
@@ -94,15 +94,15 @@ public final class AttachmentUploadJob extends BaseJob {
 
   @Override
   public void onRun() throws Exception {
-    final ResumableUploadSpec resumableUploadSpec;
-    if (FeatureFlags.attachmentsV3()) {
-      Data inputData = requireInputData();
-      if (!inputData.hasString(ResumableUploadSpecJob.KEY_RESUME_SPEC)) {
-        throw new ResumeLocationInvalidException("V3 Attachment upload requires a ResumableUploadSpec");
-      }
+    Data inputData = getInputData();
 
+    ResumableUploadSpec resumableUploadSpec;
+
+    if (inputData != null && inputData.hasString(ResumableUploadSpecJob.KEY_RESUME_SPEC)) {
+      Log.d(TAG, "Using attachments V3");
       resumableUploadSpec = ResumableUploadSpec.deserialize(inputData.getString(ResumableUploadSpecJob.KEY_RESUME_SPEC));
     } else {
+      Log.d(TAG, "Using attachments V2");
       resumableUploadSpec = null;
     }
 
diff --git a/app/src/main/java/org/thoughtcrime/securesms/jobs/PushSendJob.java b/app/src/main/java/org/thoughtcrime/securesms/jobs/PushSendJob.java
index 745e5e94c..2ccd7812e 100644
--- a/app/src/main/java/org/thoughtcrime/securesms/jobs/PushSendJob.java
+++ b/app/src/main/java/org/thoughtcrime/securesms/jobs/PushSendJob.java
@@ -168,10 +168,16 @@ public abstract class PushSendJob extends SendJob {
     return new HashSet<>(Stream.of(attachments).map(a -> {
                                                  AttachmentUploadJob attachmentUploadJob = new AttachmentUploadJob(((DatabaseAttachment) a).getAttachmentId());
 
-                                                 jobManager.startChain(AttachmentCompressionJob.fromAttachment((DatabaseAttachment) a, false, -1))
-                                                           .then(new ResumableUploadSpecJob())
-                                                           .then(attachmentUploadJob)
-                                                           .enqueue();
+                                                 if (message.isGroup()) {
+                                                   jobManager.startChain(AttachmentCompressionJob.fromAttachment((DatabaseAttachment) a, false, -1))
+                                                             .then(attachmentUploadJob)
+                                                             .enqueue();
+                                                 } else {
+                                                   jobManager.startChain(AttachmentCompressionJob.fromAttachment((DatabaseAttachment) a, false, -1))
+                                                             .then(new ResumableUploadSpecJob())
+                                                             .then(attachmentUploadJob)
+                                                             .enqueue();
+                                                 }
 
                                                  return attachmentUploadJob.getId();
                                                })
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 90ef035e7..9b7d16fbb 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
@@ -381,7 +381,7 @@ public class SignalServiceMessageSender {
                                                                  attachment.getCancelationSignal(),
                                                                  attachment.getResumableUploadSpec().orNull());
 
-    if (attachmentsV3.get()) {
+    if (attachment.getResumableUploadSpec().isPresent()) {
       return uploadAttachmentV3(attachment, attachmentKey, attachmentData);
     } else {
       return uploadAttachmentV2(attachment, attachmentKey, attachmentData);