diff --git a/backend/src/routes/coaching.js b/backend/src/routes/coaching.js
index b331aee..276df21 100644
--- a/backend/src/routes/coaching.js
+++ b/backend/src/routes/coaching.js
@@ -122,7 +122,10 @@ async function transcribeAudioFile(audioFile) {
   }
 
   if (!response.ok) {
-    throw new Error(`Transcription request failed with ${response.status}: ${JSON.stringify(payload)}`);
+    return {
+      status: response.status,
+      body: payload,
+    };
   }
 
   const text = payload.text || payload.transcript || payload.output_text;
diff --git a/frontend/src/pages/session-memory.tsx b/frontend/src/pages/session-memory.tsx
index 1b72160..560761d 100644
--- a/frontend/src/pages/session-memory.tsx
+++ b/frontend/src/pages/session-memory.tsx
@@ -102,6 +102,28 @@ function StatusPill({ status }: { status?: string }) {
   );
 }
 
+function requestErrorMessage(error: unknown, fallback: string) {
+  if (!axios.isAxiosError(error)) {
+    return fallback;
+  }
+
+  const data = error.response?.data;
+
+  if (typeof data?.message === 'string') {
+    return data.message;
+  }
+
+  if (typeof data?.error === 'string') {
+    return data.error;
+  }
+
+  if (typeof data?.error?.message === 'string') {
+    return data.error.message;
+  }
+
+  return fallback;
+}
+
 const emptyDraft: MemoryDraft = {
   title: '',
   ai_summary: '',
@@ -171,15 +193,7 @@ const SessionMemory = () => {
       });
       setNotice('Draft generated. Review and edit before saving.');
     } catch (error) {
-      if (axios.isAxiosError(error)) {
-        setNotice(
-          error.response?.data?.message ||
-            error.response?.data?.error ||
-            'Memory generation failed.',
-        );
-      } else {
-        setNotice('Memory generation failed.');
-      }
+      setNotice(requestErrorMessage(error, 'Memory generation failed.'));
     } finally {
       setIsGenerating(false);
     }
@@ -206,15 +220,7 @@ const SessionMemory = () => {
       setTranscript(response.data.text || '');
       setNotice('Audio transcribed. Review the transcript before generating memory.');
     } catch (error) {
-      if (axios.isAxiosError(error)) {
-        setNotice(
-          error.response?.data?.message ||
-            error.response?.data?.error ||
-            'Audio transcription failed.',
-        );
-      } else {
-        setNotice('Audio transcription failed.');
-      }
+      setNotice(requestErrorMessage(error, 'Audio transcription failed.'));
     } finally {
       setIsTranscribing(false);
     }