diff --git a/README.md b/README.md
index d79213a0..1261a634 100644
--- a/README.md
+++ b/README.md
@@ -6,6 +6,8 @@ PRs for small fixes are more than welcome.
 
 ## Deploying a new release
 
+Ensure `.env.local` points to `https://app.revolt.chat/api`.
+
 ```bash
 cd ~/deployments/revite
 git pull
diff --git a/src/components/common/messaging/MessageBox.tsx b/src/components/common/messaging/MessageBox.tsx
index 69b425be..78c26981 100644
--- a/src/components/common/messaging/MessageBox.tsx
+++ b/src/components/common/messaging/MessageBox.tsx
@@ -324,7 +324,7 @@ export default observer(({ channel }: Props) => {
             return;
 
         const content = state.draft.get(channel._id)?.content?.trim() ?? "";
-        if (uploadState.type === "attached") return sendFile(content);
+        if (uploadState.type !== "none") return sendFile(content);
         if (content.length === 0) return;
 
         internalEmit("NewMessages", "hide");
@@ -406,7 +406,9 @@ export default observer(({ channel }: Props) => {
      * @returns
      */
     async function sendFile(content: string) {
-        if (uploadState.type !== "attached") return;
+        if (uploadState.type !== "attached" && uploadState.type !== "failed")
+            return;
+
         const attachments: string[] = [];
         setMessage;