diff --git a/app/src/main/java/org/thoughtcrime/securesms/sms/MessageSender.java b/app/src/main/java/org/thoughtcrime/securesms/sms/MessageSender.java
index 7028fb6d6..97f89ce3f 100644
--- a/app/src/main/java/org/thoughtcrime/securesms/sms/MessageSender.java
+++ b/app/src/main/java/org/thoughtcrime/securesms/sms/MessageSender.java
@@ -289,7 +289,7 @@ public class MessageSender {
                                                   final long threadId,
                                                   final SmsDatabase.InsertListener insertListener)
   {
-    Log.i(TAG, "Sending media message with pre-uploads to " + message.getRecipient().getId() + ", thread: " + threadId);
+    Log.i(TAG, "Sending media message with pre-uploads to " + message.getRecipient().getId() + ", thread: " + threadId + ", pre-uploads: " +  preUploadResults);
     Preconditions.checkArgument(message.getAttachments().isEmpty(), "If the media is pre-uploaded, there should be no attachments on the message.");
 
     try {
@@ -807,6 +807,11 @@ public class MessageSender {
       ParcelUtil.writeStringCollection(dest, jobIds);
       dest.writeParcelable(media, flags);
     }
+
+    @Override
+    public @NonNull String toString() {
+      return "{ID: " + attachmentId.getRowId() + ", URI: " + media.getUri() + ", Jobs: " + jobIds.stream().map(j -> "JOB::" + j).collect(Collectors.toList()) + "}";
+    }
   }
 
   public enum MessageSentEvent {
diff --git a/app/src/main/java/org/thoughtcrime/securesms/util/ImageCompressionUtil.java b/app/src/main/java/org/thoughtcrime/securesms/util/ImageCompressionUtil.java
index 841222d25..20e2e0f18 100644
--- a/app/src/main/java/org/thoughtcrime/securesms/util/ImageCompressionUtil.java
+++ b/app/src/main/java/org/thoughtcrime/securesms/util/ImageCompressionUtil.java
@@ -9,7 +9,9 @@ import androidx.annotation.Nullable;
 import androidx.annotation.WorkerThread;
 
 import com.bumptech.glide.load.engine.DiskCacheStrategy;
+import com.bumptech.glide.load.engine.GlideException;
 
+import org.signal.core.util.logging.Log;
 import org.thoughtcrime.securesms.mms.GlideApp;
 
 import java.io.ByteArrayOutputStream;
@@ -17,6 +19,8 @@ import java.util.concurrent.ExecutionException;
 
 public final class ImageCompressionUtil {
 
+  private static final String TAG = Log.tag(ImageCompressionUtil.class);
+
   private ImageCompressionUtil () {}
 
   /**
@@ -63,6 +67,9 @@ public final class ImageCompressionUtil {
                              .submit(maxDimension, maxDimension)
                              .get();
     } catch (ExecutionException | InterruptedException e) {
+      if (e.getCause() instanceof GlideException) {
+        ((GlideException) e.getCause()).logRootCauses(TAG);
+      }
       throw new BitmapDecodingException(e);
     }