diff --git a/bin/gstack-telemetry-log b/bin/gstack-telemetry-log
index edcbdbab..5edde6dd 100755
--- a/bin/gstack-telemetry-log
+++ b/bin/gstack-telemetry-log
@@ -32,17 +32,21 @@ OUTCOME="unknown"
 USED_BROWSE="false"
 SESSION_ID=""
 ERROR_CLASS=""
+ERROR_MESSAGE=""
+FAILED_STEP=""
 EVENT_TYPE="skill_run"
 
 while [ $# -gt 0 ]; do
   case "$1" in
-    --skill)       SKILL="$2"; shift 2 ;;
-    --duration)    DURATION="$2"; shift 2 ;;
-    --outcome)     OUTCOME="$2"; shift 2 ;;
-    --used-browse) USED_BROWSE="$2"; shift 2 ;;
-    --session-id)  SESSION_ID="$2"; shift 2 ;;
-    --error-class) ERROR_CLASS="$2"; shift 2 ;;
-    --event-type)  EVENT_TYPE="$2"; shift 2 ;;
+    --skill)         SKILL="$2"; shift 2 ;;
+    --duration)      DURATION="$2"; shift 2 ;;
+    --outcome)       OUTCOME="$2"; shift 2 ;;
+    --used-browse)   USED_BROWSE="$2"; shift 2 ;;
+    --session-id)    SESSION_ID="$2"; shift 2 ;;
+    --error-class)   ERROR_CLASS="$2"; shift 2 ;;
+    --error-message) ERROR_MESSAGE="$2"; shift 2 ;;
+    --failed-step)   FAILED_STEP="$2"; shift 2 ;;
+    --event-type)    EVENT_TYPE="$2"; shift 2 ;;
     *) shift ;;
   esac
 done
@@ -135,6 +139,12 @@ mkdir -p "$ANALYTICS_DIR"
 ERR_FIELD="null"
 [ -n "$ERROR_CLASS" ] && ERR_FIELD="\"$ERROR_CLASS\""
 
+ERR_MSG_FIELD="null"
+[ -n "$ERROR_MESSAGE" ] && ERR_MSG_FIELD="\"$(echo "$ERROR_MESSAGE" | head -c 200 | sed 's/"/\\"/g')\""
+
+STEP_FIELD="null"
+[ -n "$FAILED_STEP" ] && STEP_FIELD="\"$(echo "$FAILED_STEP" | head -c 30)\""
+
 DUR_FIELD="null"
 [ -n "$DURATION" ] && DUR_FIELD="$DURATION"
 
@@ -144,9 +154,10 @@ INSTALL_FIELD="null"
 BROWSE_BOOL="false"
 [ "$USED_BROWSE" = "true" ] && BROWSE_BOOL="true"
 
-printf '{"v":1,"ts":"%s","event_type":"%s","skill":"%s","session_id":"%s","gstack_version":"%s","os":"%s","arch":"%s","duration_s":%s,"outcome":"%s","error_class":%s,"used_browse":%s,"sessions":%s,"installation_id":%s,"_repo_slug":"%s","_branch":"%s"}\n' \
+printf '{"v":1,"ts":"%s","event_type":"%s","skill":"%s","session_id":"%s","gstack_version":"%s","os":"%s","arch":"%s","duration_s":%s,"outcome":"%s","error_class":%s,"error_message":%s,"failed_step":%s,"used_browse":%s,"sessions":%s,"installation_id":%s,"_repo_slug":"%s","_branch":"%s"}\n' \
   "$TS" "$EVENT_TYPE" "$SKILL" "$SESSION_ID" "$GSTACK_VERSION" "$OS" "$ARCH" \
-  "$DUR_FIELD" "$OUTCOME" "$ERR_FIELD" "$BROWSE_BOOL" "${SESSIONS:-1}" \
+  "$DUR_FIELD" "$OUTCOME" "$ERR_FIELD" "$ERR_MSG_FIELD" "$STEP_FIELD" \
+  "$BROWSE_BOOL" "${SESSIONS:-1}" \
   "$INSTALL_FIELD" "$REPO_SLUG" "$BRANCH" >> "$JSONL_FILE" 2>/dev/null || true
 
 # ─── Trigger sync if tier is not off ─────────────────────────
diff --git a/supabase/functions/telemetry-ingest/index.ts b/supabase/functions/telemetry-ingest/index.ts
index 07d65d36..248c7d91 100644
--- a/supabase/functions/telemetry-ingest/index.ts
+++ b/supabase/functions/telemetry-ingest/index.ts
@@ -16,6 +16,8 @@ interface TelemetryEvent {
   duration_s?: number;
   outcome: string;
   error_class?: string;
+  error_message?: string;
+  failed_step?: string;
   used_browse?: boolean;
   sessions?: number;
   installation_id?: string;
@@ -77,6 +79,8 @@ Deno.serve(async (req) => {
         duration_s: typeof event.duration_s === "number" ? event.duration_s : null,
         outcome: String(event.outcome).slice(0, 20),
         error_class: event.error_class ? String(event.error_class).slice(0, 100) : null,
+        error_message: event.error_message ? String(event.error_message).slice(0, 200) : null,
+        failed_step: event.failed_step ? String(event.failed_step).slice(0, 30) : null,
         used_browse: event.used_browse === true,
         concurrent_sessions: typeof event.sessions === "number" ? event.sessions : 1,
         installation_id: event.installation_id ? String(event.installation_id).slice(0, 64) : null,
diff --git a/supabase/migrations/002_community_tier.sql b/supabase/migrations/002_community_tier.sql
index 5bf0b789..3b46d847 100644
--- a/supabase/migrations/002_community_tier.sql
+++ b/supabase/migrations/002_community_tier.sql
@@ -1,5 +1,9 @@
 -- gstack community tier schema
--- Adds authenticated backup, benchmarks, and email to the telemetry platform.
+-- Adds authenticated backup, benchmarks, email, and richer error telemetry.
+
+-- Add error context columns to telemetry_events
+ALTER TABLE telemetry_events ADD COLUMN error_message TEXT;
+ALTER TABLE telemetry_events ADD COLUMN failed_step TEXT;
 
 -- Add columns to installations for backup + email + auth identity
 ALTER TABLE installations ADD COLUMN user_id UUID;