diff --git a/api/prisma/migrate-entrypoint.sh b/api/prisma/migrate-entrypoint.sh
index e4ef3b6..7eacdcb 100755
--- a/api/prisma/migrate-entrypoint.sh
+++ b/api/prisma/migrate-entrypoint.sh
@@ -2,31 +2,42 @@
 set -e
 
 # ---------------------------------------------------------------------------
-# 1. Print current migration status for debugging.
+# Run prisma migrate deploy. On P3009 (a failed migration is blocking deploy),
+# extract the migration name from the error, resolve it as rolled-back, and
+# retry. All migration SQL in this repo is idempotent so a re-run is safe.
+# Loop handles multiple blocked migrations; max retries prevents infinite loops.
 # ---------------------------------------------------------------------------
-echo "[migrate] Checking database migration status..."
-STATUS_OUTPUT=$(bunx prisma migrate status 2>&1 || true)
-echo "$STATUS_OUTPUT"
+MAX_RETRIES=10
+ATTEMPT=0
 
-# ---------------------------------------------------------------------------
-# 2. Resolve any "Failed" migrations as rolled-back so deploy can re-apply.
-#    All migration SQL in this repo is written to be idempotent (using
-#    IF NOT EXISTS / DO $$ ... $$ guards), so a re-run after resolving will
-#    succeed even when schema drift has occurred from a prior db push.
-#
-#    Regex matches both named (20260307010000_add_foo) and unnamed (20260125205653)
-#    migration timestamps so the initial baseline migration is also covered.
-# ---------------------------------------------------------------------------
-FAILED=$(printf '%s\n' "$STATUS_OUTPUT" | grep -i "failed" | grep -oE '[0-9]{14}(_[a-zA-Z_]+)?' || true)
+while [ $ATTEMPT -lt $MAX_RETRIES ]; do
+  ATTEMPT=$((ATTEMPT + 1))
+  echo "[migrate] Running prisma migrate deploy (attempt $ATTEMPT)..."
 
-for MIGRATION in $FAILED; do
-  echo "[migrate] Resolving failed migration: $MIGRATION"
-  bunx prisma migrate resolve --rolled-back "$MIGRATION"
+  DEPLOY_OUTPUT=$(bunx prisma migrate deploy 2>&1)
+  EXIT_CODE=$?
+  echo "$DEPLOY_OUTPUT"
+
+  if [ $EXIT_CODE -eq 0 ]; then
+    echo "[migrate] All migrations applied successfully."
+    exit 0
+  fi
+
+  # P3009: a previously-failed migration is blocking deploy.
+  # The error message contains the migration name in backticks:
+  #   The `20260402000000_fix_severity_typo` migration started at ... failed
+  if echo "$DEPLOY_OUTPUT" | grep -q "P3009"; then
+    FAILED=$(echo "$DEPLOY_OUTPUT" | grep -oE '\`[0-9]{14}(_[a-zA-Z_]+)?\`' | tr -d '\`' | head -1)
+    if [ -n "$FAILED" ]; then
+      echo "[migrate] Resolving failed migration as rolled-back: $FAILED"
+      bunx prisma migrate resolve --rolled-back "$FAILED"
+      continue
+    fi
+  fi
+
+  echo "[migrate] Migration failed with a non-recoverable error."
+  exit 1
 done
 
-# ---------------------------------------------------------------------------
-# 3. Deploy all pending migrations from the migrations directory.
-# ---------------------------------------------------------------------------
-echo "[migrate] Running prisma migrate deploy..."
-bunx prisma migrate deploy
-echo "[migrate] All migrations applied successfully."
+echo "[migrate] Exceeded max retries ($MAX_RETRIES). Giving up."
+exit 1