diff --git a/app/src/main/java/org/thoughtcrime/securesms/mediasend/MediaSendActivity.java b/app/src/main/java/org/thoughtcrime/securesms/mediasend/MediaSendActivity.java
index 33e9f6993d..4026325771 100644
--- a/app/src/main/java/org/thoughtcrime/securesms/mediasend/MediaSendActivity.java
+++ b/app/src/main/java/org/thoughtcrime/securesms/mediasend/MediaSendActivity.java
@@ -718,6 +718,10 @@ public class MediaSendActivity extends PassphraseRequiredActionBarActivity imple
         case ITEM_TOO_LARGE:
           Toast.makeText(this, R.string.MediaSendActivity_an_item_was_removed_because_it_exceeded_the_size_limit, Toast.LENGTH_LONG).show();
           break;
+        case ONLY_ITEM_TOO_LARGE:
+          Toast.makeText(this, R.string.MediaSendActivity_an_item_was_removed_because_it_exceeded_the_size_limit, Toast.LENGTH_LONG).show();
+          onNoMediaAvailable();
+          break;
         case TOO_MANY_ITEMS:
           int maxSelection = viewModel.getMaxSelection();
           Toast.makeText(this, getResources().getQuantityString(R.plurals.MediaSendActivity_cant_share_more_than_n_items, maxSelection, maxSelection), Toast.LENGTH_SHORT).show();
diff --git a/app/src/main/java/org/thoughtcrime/securesms/mediasend/MediaSendViewModel.java b/app/src/main/java/org/thoughtcrime/securesms/mediasend/MediaSendViewModel.java
index 9c1ec7585c..92c8d98781 100644
--- a/app/src/main/java/org/thoughtcrime/securesms/mediasend/MediaSendViewModel.java
+++ b/app/src/main/java/org/thoughtcrime/securesms/mediasend/MediaSendViewModel.java
@@ -147,7 +147,11 @@ class MediaSendViewModel extends ViewModel {
         List<Media> filteredMedia = getFilteredMedia(context, populatedMedia, mediaConstraints);
 
         if (filteredMedia.size() != newMedia.size()) {
-          error.setValue(Error.ITEM_TOO_LARGE);
+          if (filteredMedia.isEmpty() && newMedia.size() == 1 && page == Page.UNKNOWN) {
+            error.setValue(Error.ONLY_ITEM_TOO_LARGE);
+          } else {
+            error.setValue(Error.ITEM_TOO_LARGE);
+          }
         }
 
         if (filteredMedia.size() > maxSelection) {
@@ -670,7 +674,7 @@ class MediaSendViewModel extends ViewModel {
   }
 
   enum Error {
-    ITEM_TOO_LARGE, TOO_MANY_ITEMS, NO_ITEMS
+    ITEM_TOO_LARGE, TOO_MANY_ITEMS, NO_ITEMS, ONLY_ITEM_TOO_LARGE
   }
 
   enum Event {