diff --git a/app/src/main/java/org/thoughtcrime/securesms/database/AttachmentTable.kt b/app/src/main/java/org/thoughtcrime/securesms/database/AttachmentTable.kt
index 29e4dfe418..50db514432 100644
--- a/app/src/main/java/org/thoughtcrime/securesms/database/AttachmentTable.kt
+++ b/app/src/main/java/org/thoughtcrime/securesms/database/AttachmentTable.kt
@@ -1044,6 +1044,7 @@ class AttachmentTable(
 
   @Throws(MmsException::class)
   fun insertAttachmentForPreUpload(attachment: Attachment): DatabaseAttachment {
+    Log.d(TAG, "Inserting attachment $attachment for pre-upload.")
     val result = insertAttachmentsForMessage(PREUPLOAD_MESSAGE_ID, listOf(attachment), emptyList())
 
     if (result.values.isEmpty()) {
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 07cf66e5bb..9a94086a42 100644
--- a/app/src/main/java/org/thoughtcrime/securesms/jobs/PushSendJob.java
+++ b/app/src/main/java/org/thoughtcrime/securesms/jobs/PushSendJob.java
@@ -26,6 +26,7 @@ import org.signal.libsignal.zkgroup.InvalidInputException;
 import org.signal.libsignal.zkgroup.receipts.ReceiptCredentialPresentation;
 import org.thoughtcrime.securesms.TextSecureExpiredException;
 import org.thoughtcrime.securesms.attachments.Attachment;
+import org.thoughtcrime.securesms.attachments.AttachmentId;
 import org.thoughtcrime.securesms.attachments.DatabaseAttachment;
 import org.thoughtcrime.securesms.blurhash.BlurHash;
 import org.thoughtcrime.securesms.contactshare.Contact;
@@ -248,15 +249,17 @@ public abstract class PushSendJob extends SendJob {
                              .toList());
 
     return new HashSet<>(Stream.of(attachments).map(a -> {
-                                                 AttachmentUploadJob attachmentUploadJob = new AttachmentUploadJob(((DatabaseAttachment) a).attachmentId);
+                                 final AttachmentId attachmentId = ((DatabaseAttachment) a).attachmentId;
+                                 Log.d(TAG, "Enqueueing job chain to upload " + attachmentId);
+                                 AttachmentUploadJob attachmentUploadJob = new AttachmentUploadJob(attachmentId);
 
-                                                 jobManager.startChain(AttachmentCompressionJob.fromAttachment((DatabaseAttachment) a, false, -1))
-                                                           .then(attachmentUploadJob)
-                                                           .enqueue();
+                                 jobManager.startChain(AttachmentCompressionJob.fromAttachment((DatabaseAttachment) a, false, -1))
+                                           .then(attachmentUploadJob)
+                                           .enqueue();
 
-                                                 return attachmentUploadJob.getId();
-                                               })
-                                               .toList());
+                                 return attachmentUploadJob.getId();
+                               })
+                               .toList());
   }
 
   protected @NonNull List<SignalServiceAttachment> getAttachmentPointersFor(List<Attachment> attachments) {
diff --git a/app/src/main/java/org/thoughtcrime/securesms/mediasend/MediaUploadRepository.java b/app/src/main/java/org/thoughtcrime/securesms/mediasend/MediaUploadRepository.java
index 52b6737562..56af8c3229 100644
--- a/app/src/main/java/org/thoughtcrime/securesms/mediasend/MediaUploadRepository.java
+++ b/app/src/main/java/org/thoughtcrime/securesms/mediasend/MediaUploadRepository.java
@@ -67,7 +67,9 @@ public class MediaUploadRepository {
   public void startUpload(@NonNull Collection<Media> mediaItems, @Nullable Recipient recipient) {
     executor.execute(() -> {
       for (Media media : mediaItems) {
+        Log.d(TAG, "Canceling existing preuploads.");
         cancelUploadInternal(media);
+        Log.d(TAG, "Re-uploading media with recipient.");
         uploadMediaInternal(media, recipient);
       }
     });
@@ -85,7 +87,9 @@ public class MediaUploadRepository {
         boolean same     = oldMedia.equals(newMedia) && hasSameTransformProperties(oldMedia, newMedia);
 
         if (!same || !uploadResults.containsKey(newMedia)) {
+          Log.d(TAG, "Canceling existing preuploads.");
           cancelUploadInternal(oldMedia);
+          Log.d(TAG, "Applying media updates.");
           uploadMediaInternal(newMedia, recipient);
         }
       }
@@ -104,6 +108,7 @@ public class MediaUploadRepository {
   }
 
   public void cancelUpload(@NonNull Media media) {
+    Log.d(TAG, "User canceling media upload.");
     executor.execute(() -> cancelUploadInternal(media));
   }
 
diff --git a/app/src/main/java/org/thoughtcrime/securesms/mediasend/v2/MediaSelectionRepository.kt b/app/src/main/java/org/thoughtcrime/securesms/mediasend/v2/MediaSelectionRepository.kt
index 65e55afbc3..958e40841e 100644
--- a/app/src/main/java/org/thoughtcrime/securesms/mediasend/v2/MediaSelectionRepository.kt
+++ b/app/src/main/java/org/thoughtcrime/securesms/mediasend/v2/MediaSelectionRepository.kt
@@ -104,7 +104,9 @@ class MediaSelectionRepository(context: Context) {
       val updatedMedia = oldToNewMediaMap.values.toList()
 
       for (media in updatedMedia) {
-        Log.w(TAG, media.uri.toString() + " : " + media.transformProperties.map { t: TransformProperties -> "" + t.videoTrim }.orElse("null"))
+        val uri: Uri = media.uri
+        val transformProperties: Boolean? = media.transformProperties.map { it.videoTrim }.orElse(null)
+        Log.w(TAG, "$uri : trimmed=$transformProperties")
       }
 
       val singleRecipient: Recipient? = singleContact?.let { Recipient.resolved(it.recipientId) }
diff --git a/app/src/main/java/org/thoughtcrime/securesms/mediasend/v2/review/MediaReviewFragment.kt b/app/src/main/java/org/thoughtcrime/securesms/mediasend/v2/review/MediaReviewFragment.kt
index ca54cd7a47..64b42f915a 100644
--- a/app/src/main/java/org/thoughtcrime/securesms/mediasend/v2/review/MediaReviewFragment.kt
+++ b/app/src/main/java/org/thoughtcrime/securesms/mediasend/v2/review/MediaReviewFragment.kt
@@ -189,12 +189,14 @@ class MediaReviewFragment : Fragment(R.layout.v2_media_review_fragment), Schedul
 
     val multiselectLauncher = registerForActivityResult(multiselectContract) { keys ->
       if (keys.isNotEmpty()) {
+        Log.d(TAG, "Performing send from multi-select activity result.")
         performSend(keys)
       }
     }
 
     val storiesLauncher = registerForActivityResult(storiesContract) { keys ->
       if (keys.isNotEmpty()) {
+        Log.d(TAG, "Performing send from stories activity result.")
         performSend(keys)
       }
     }
@@ -243,11 +245,15 @@ class MediaReviewFragment : Fragment(R.layout.v2_media_review_fragment), Schedul
       } else if (sharedViewModel.isAddToGroupStoryFlow) {
         MaterialAlertDialogBuilder(requireContext())
           .setMessage(getString(R.string.MediaReviewFragment__add_to_the_group_story, sharedViewModel.state.value!!.recipient!!.getDisplayName(requireContext())))
-          .setPositiveButton(R.string.MediaReviewFragment__add_to_story) { _, _ -> performSend() }
+          .setPositiveButton(R.string.MediaReviewFragment__add_to_story) { _, _ ->
+            Log.d(TAG, "Performing send add to group story dialog.")
+            performSend()
+          }
           .setNegativeButton(android.R.string.cancel) { _, _ -> }
           .show()
         scheduledSendTime = null
       } else {
+        Log.d(TAG, "Performing send from send button.")
         performSend()
       }
     }