diff --git a/packages/core/src/database/migration.ts b/packages/core/src/database/migration.ts
index c9a7dd02b9d..b89a81e3eb8 100644
--- a/packages/core/src/database/migration.ts
+++ b/packages/core/src/database/migration.ts
@@ -23,6 +23,7 @@ export function applyOnly(db: Database, input: Migration[]) {
     yield* db.run(
       sql`CREATE TABLE IF NOT EXISTS ${sql.identifier("migration")} (id TEXT PRIMARY KEY, time_completed INTEGER NOT NULL)`,
     )
+    const skipMigrations = !!process.env.OPENCODE_SKIP_MIGRATIONS
     let completed = new Set(
       (yield* db.all<{ id: string }>(sql`SELECT id FROM ${sql.identifier("migration")}`)).map((row) => row.id),
     )
@@ -43,12 +44,14 @@ export function applyOnly(db: Database, input: Migration[]) {
         )
       }
     }
+    if (!skipMigrations) yield* repairKnownSchemaDrift(db, input, completed)
 
     for (const migration of input) {
       if (completed.has(migration.id)) continue
+      if (skipMigrations) continue
       yield* db.transaction((tx) =>
         Effect.gen(function* () {
-          if (!process.env.OPENCODE_SKIP_MIGRATIONS) yield* migration.up(tx)
+          yield* migration.up(tx)
           yield* tx.run(
             sql`INSERT INTO ${sql.identifier("migration")} (id, time_completed) VALUES (${migration.id}, ${Date.now()})`,
           )
@@ -57,3 +60,15 @@ export function applyOnly(db: Database, input: Migration[]) {
     }
   })
 }
+
+function repairKnownSchemaDrift(db: Database, input: Migration[], completed: Set<string>) {
+  return Effect.gen(function* () {
+    const sessionMetadata = input.find((migration) => migration.id === "20260511173437_session-metadata")
+    if (!sessionMetadata) return
+    if (!completed.has(sessionMetadata.id)) return
+    if (!(yield* db.get(sql`SELECT name FROM sqlite_master WHERE type = 'table' AND name = ${"session"}`))) return
+
+    // Older Drizzle skip-migration runs could record this id without applying its SQL.
+    yield* db.transaction((tx) => sessionMetadata.up(tx))
+  })
+}
diff --git a/packages/core/test/database-migration.test.ts b/packages/core/test/database-migration.test.ts
index 52c1e920ad4..85e9d8907a3 100644
--- a/packages/core/test/database-migration.test.ts
+++ b/packages/core/test/database-migration.test.ts
@@ -426,6 +426,88 @@ describe("DatabaseMigration", () => {
     )
   })
 
+  test("runs session metadata migration after importing older drizzle state", async () => {
+    await run(
+      Effect.gen(function* () {
+        const db = yield* makeDb
+        yield* db.run(sql`CREATE TABLE session (id text PRIMARY KEY)`)
+        yield* db.run(
+          sql`CREATE TABLE __drizzle_migrations (id INTEGER PRIMARY KEY, hash text NOT NULL, created_at numeric, name text, applied_at TEXT)`,
+        )
+        yield* db.run(sql`
+          INSERT INTO __drizzle_migrations (hash, created_at, name, applied_at)
+          VALUES ('hash', 1, '20260511000411_data_migration_state', ${new Date().toISOString()})
+        `)
+
+        yield* DatabaseMigration.applyOnly(db, [sessionMetadataMigration])
+
+        expect(
+          (yield* db.all<{ name: string }>(sql`PRAGMA table_info(session)`)).map((column) => column.name),
+        ).toContain("metadata")
+        expect(yield* db.all(sql`SELECT id FROM migration ORDER BY id`)).toEqual([
+          { id: "20260511000411_data_migration_state" },
+          { id: "20260511173437_session-metadata" },
+        ])
+      }),
+    )
+  })
+
+  test("repairs imported session metadata migration state when the column is missing", async () => {
+    await run(
+      Effect.gen(function* () {
+        const db = yield* makeDb
+        yield* db.run(sql`CREATE TABLE session (id text PRIMARY KEY)`)
+        yield* db.run(
+          sql`CREATE TABLE __drizzle_migrations (id INTEGER PRIMARY KEY, hash text NOT NULL, created_at numeric, name text, applied_at TEXT)`,
+        )
+        yield* db.run(sql`
+          INSERT INTO __drizzle_migrations (hash, created_at, name, applied_at)
+          VALUES ('hash', 1, '20260511173437_session-metadata', ${new Date().toISOString()})
+        `)
+
+        yield* DatabaseMigration.applyOnly(db, [sessionMetadataMigration])
+
+        expect(
+          (yield* db.all<{ name: string }>(sql`PRAGMA table_info(session)`)).map((column) => column.name),
+        ).toContain("metadata")
+        expect(yield* db.all(sql`SELECT id FROM migration ORDER BY id`)).toEqual([
+          { id: "20260511173437_session-metadata" },
+        ])
+      }),
+    )
+  })
+
+  test("does not record migrations as complete when migrations are skipped", async () => {
+    const previous = process.env.OPENCODE_SKIP_MIGRATIONS
+    try {
+      await run(
+        Effect.gen(function* () {
+          const db = yield* makeDb
+          yield* db.run(sql`CREATE TABLE session (id text PRIMARY KEY)`)
+
+          process.env.OPENCODE_SKIP_MIGRATIONS = "true"
+          yield* DatabaseMigration.applyOnly(db, [sessionMetadataMigration])
+
+          expect(yield* db.all(sql`SELECT id FROM migration`)).toEqual([])
+          expect(
+            (yield* db.all<{ name: string }>(sql`PRAGMA table_info(session)`)).map((column) => column.name),
+          ).not.toContain("metadata")
+
+          delete process.env.OPENCODE_SKIP_MIGRATIONS
+          yield* DatabaseMigration.applyOnly(db, [sessionMetadataMigration])
+
+          expect(yield* db.all(sql`SELECT id FROM migration`)).toEqual([{ id: "20260511173437_session-metadata" }])
+          expect(
+            (yield* db.all<{ name: string }>(sql`PRAGMA table_info(session)`)).map((column) => column.name),
+          ).toContain("metadata")
+        }),
+      )
+    } finally {
+      if (previous === undefined) delete process.env.OPENCODE_SKIP_MIGRATIONS
+      else process.env.OPENCODE_SKIP_MIGRATIONS = previous
+    }
+  })
+
   test("does not replay a migrated session metadata column", async () => {
     await run(
       Effect.gen(function* () {