diff --git a/CHANGELOG.md b/CHANGELOG.md
index 87286a156b..dddf7c0b4d 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -10,6 +10,8 @@ This is the log of notable changes to EAS CLI and related packages.
 
 ### 🐛 Bug fixes
 
+- Show `eas deploy` upload error messages. ([#2771](https://github.com/expo/eas-cli/pull/2771) by [@kadikraman](https://github.com/kadikraman))
+
 ### 🧹 Chores
 
 ## [14.2.0](https://github.com/expo/eas-cli/releases/tag/v14.2.0) - 2024-12-13
diff --git a/packages/eas-cli/src/worker/upload.ts b/packages/eas-cli/src/worker/upload.ts
index 03f1177458..25e0f93312 100644
--- a/packages/eas-cli/src/worker/upload.ts
+++ b/packages/eas-cli/src/worker/upload.ts
@@ -109,20 +109,21 @@ export async function uploadAsync(params: UploadParams): Promise<UploadResult> {
         return retry(error);
       }
 
+      const body = await response.json().catch(() => null);
+      const errorMessage = body?.error ?? `Upload of "${filePath}" failed: ${response.statusText}`;
+
       if (
         response.status === 408 ||
         response.status === 409 ||
         response.status === 429 ||
         (response.status >= 500 && response.status <= 599)
       ) {
-        const message = `Upload of "${filePath}" failed: ${response.statusText}`;
-        const text = await response.text().catch(() => null);
-        return retry(new Error(text ? `${message}\n${text}` : message));
+        return retry(new Error(errorMessage));
       } else if (response.status === 413) {
         const message = `Upload of "${filePath}" failed: File size exceeded the upload limit`;
         throw new Error(message);
       } else if (!response.ok) {
-        throw new Error(`Upload of "${filePath}" failed: ${response.statusText}`);
+        throw new Error(errorMessage);
       }
 
       return {