diff --git a/apps/server/Dockerfile b/apps/server/Dockerfile
index 387be940b..fe0aef534 100644
--- a/apps/server/Dockerfile
+++ b/apps/server/Dockerfile
@@ -15,7 +15,25 @@ COPY packages/server-sdk-shared packages/server-sdk-shared
 RUN --mount=type=cache,id=pnpm-store,target=/root/.pnpm-store \
     pnpm install --frozen-lockfile --ignore-scripts
 
-RUN pnpm -F @proj-airi/server-schema run build
+# NOTICE:
+# Force a fresh build of server-schema and assert that
+# unplugin-drizzle-orm-migrations actually replaced the `virtual:drizzle-migrations.sql`
+# import. Without this guard a layer built when the rolldown plugin silently
+# no-op'd (intermittently observed on Railway with tsdown 0.21.9 + rolldown
+# 1.0.0-rc.16) ships a dist/index.mjs that re-exports the literal `virtual:`
+# specifier, which crashes at runtime under tsx with
+# ERR_UNSUPPORTED_ESM_URL_SCHEME. `rm -rf dist` keeps this RUN's command-string
+# distinct from earlier cached variants and prevents a stale dist from masking
+# a failed transform.
+RUN rm -rf packages/server-schema/dist \
+ && pnpm -F @proj-airi/server-schema run build \
+ && if grep -qE "from ['\"]virtual:" packages/server-schema/dist/index.mjs; then \
+      echo "ERROR: server-schema dist/index.mjs still references a virtual: specifier — unplugin-drizzle-orm-migrations transform did not run." >&2; \
+      cat packages/server-schema/dist/index.mjs >&2; \
+      exit 1; \
+    fi \
+ && ls packages/server-schema/dist/virtual_drizzle-migrations-*.mjs >/dev/null
+
 RUN pnpm -F @proj-airi/server-sdk-shared run build
 RUN pnpm -F @proj-airi/server run build
 
diff --git a/apps/server/production/railway/Dockerfile b/apps/server/production/railway/Dockerfile
index 5cc76d694..770c7d548 100644
--- a/apps/server/production/railway/Dockerfile
+++ b/apps/server/production/railway/Dockerfile
@@ -13,7 +13,25 @@ COPY packages/server-sdk-shared packages/server-sdk-shared
 
 RUN pnpm install --frozen-lockfile --ignore-scripts
 
-RUN pnpm -F @proj-airi/server-schema run build
+# NOTICE:
+# Force a fresh build of server-schema and assert that
+# unplugin-drizzle-orm-migrations actually replaced the `virtual:drizzle-migrations.sql`
+# import. Without this guard a layer built when the rolldown plugin silently
+# no-op'd (intermittently observed on Railway with tsdown 0.21.9 + rolldown
+# 1.0.0-rc.16) ships a dist/index.mjs that re-exports the literal `virtual:`
+# specifier, which crashes at runtime under tsx with
+# ERR_UNSUPPORTED_ESM_URL_SCHEME. `rm -rf dist` keeps this RUN's command-string
+# distinct from earlier cached variants and prevents a stale dist from masking
+# a failed transform.
+RUN rm -rf packages/server-schema/dist \
+ && pnpm -F @proj-airi/server-schema run build \
+ && if grep -qE "from ['\"]virtual:" packages/server-schema/dist/index.mjs; then \
+      echo "ERROR: server-schema dist/index.mjs still references a virtual: specifier — unplugin-drizzle-orm-migrations transform did not run." >&2; \
+      cat packages/server-schema/dist/index.mjs >&2; \
+      exit 1; \
+    fi \
+ && ls packages/server-schema/dist/virtual_drizzle-migrations-*.mjs >/dev/null
+
 RUN pnpm -F @proj-airi/server-sdk-shared run build
 RUN pnpm -F @proj-airi/server run build