diff --git a/web/input/input-state-container.react.js b/web/input/input-state-container.react.js
--- a/web/input/input-state-container.react.js
+++ b/web/input/input-state-container.react.js
@@ -616,7 +616,7 @@
           localID: getNextLocalUploadID(),
           serverID: null,
           messageID: null,
-          failed: null,
+          failed: false,
           file: fixedFile,
           mediaType,
           dimensions,
@@ -855,7 +855,6 @@
         // The upload has been cancelled or completed before it failed
         return {};
       }
-      const failed = e instanceof Error && e.message ? e.message : 'failed';
       return {
         pendingUploads: {
           ...prevState.pendingUploads,
@@ -863,7 +862,9 @@
             ...uploads,
             [localUploadID]: {
               ...upload,
-              failed,
+              failed: true,
+              failureMessage:
+                e instanceof Error && e.message ? e.message : 'failed',
               progressPercent: 0,
               abort: null,
             },
@@ -1173,7 +1174,7 @@
         if (uploadIDsToRetry.has(localID) && !pendingUpload.serverID) {
           newPendingUploads[localID] = {
             ...pendingUpload,
-            failed: null,
+            failed: false,
             progressPercent: 0,
             abort: null,
           };
diff --git a/web/input/input-state.js b/web/input/input-state.js
--- a/web/input/input-state.js
+++ b/web/input/input-state.js
@@ -16,8 +16,9 @@
   serverID: ?string,
   // Pending uploads are assigned a messageID once they are sent
   messageID: ?string,
-  // This is set to truthy if the upload fails for whatever reason
-  failed: ?string,
+  // This is set to true if the upload fails for whatever reason
+  failed: boolean,
+  failureMessage?: string,
   file: File,
   mediaType: MediaType,
   dimensions: ?Dimensions,