coder
diff --git a/‎coderd/database/migrations/000262_site_to_crypto_key.up.sql
-52 b/‎coderd/database/migrations/000262_site_to_crypto_key.up.sql
-52
diff --git a/‎coderd/database/migrations/000262_site_to_crypto_key.down.sql renamed to ‎coderd/database/migrations/000264_cryptokey_features.down.sql
+5-6 b/‎coderd/database/migrations/000262_site_to_crypto_key.down.sql renamed to ‎coderd/database/migrations/000264_cryptokey_features.down.sql
+5-6
diff --git a/‎coderd/database/migrations/000264_cryptokey_features.up.sql
+18 b/‎coderd/database/migrations/000264_cryptokey_features.up.sql
+18
diff --git a/‎coderd/database/migrations/testdata/fixtures/000262_site_to_crypto_key.up.sql
-15 b/‎coderd/database/migrations/testdata/fixtures/000262_site_to_crypto_key.up.sql
-15
diff --git a/‎coderd/database/migrations/testdata/fixtures/000264_cryptokey_features.up.sql
+40 b/‎coderd/database/migrations/testdata/fixtures/000264_cryptokey_features.up.sql
+40
@@ -1,19 +1,18 @@
 -- Step 1: Remove the new entries from crypto_keys table
 DELETE FROM crypto_keys
-WHERE feature IN ('workspace_apps_token', 'workspace_apps_api_key', 'tailnet_resume')
-  AND sequence = 1;
+WHERE feature IN ('workspace_apps_token', 'workspace_apps_api_key');
 
-CREATE TYPE crypto_key_feature_old AS ENUM (
+CREATE TYPE old_crypto_key_feature AS ENUM (
     'workspace_apps',
     'oidc_convert',
     'tailnet_resume'
 );
 
 ALTER TABLE crypto_keys
-    ALTER COLUMN feature TYPE crypto_key_feature_old
-    USING (feature::text::crypto_key_feature_old);
+    ALTER COLUMN feature TYPE old_crypto_key_feature
+    USING (feature::text::old_crypto_key_feature);
 
 DROP TYPE crypto_key_feature;
 
-ALTER TYPE crypto_key_feature_old RENAME TO crypto_key_feature;
+ALTER TYPE old_crypto_key_feature RENAME TO crypto_key_feature;
 
@@ -0,0 +1,18 @@
+-- Create a new enum type with the desired values
+CREATE TYPE new_crypto_key_feature AS ENUM (
+    'workspace_apps_token',
+    'workspace_apps_api_key',
+    'oidc_convert',
+    'tailnet_resume'
+);
+
+DELETE FROM crypto_keys WHERE feature = 'workspace_apps';
+
+-- Drop the old type and rename the new one
+ALTER TABLE crypto_keys
+    ALTER COLUMN feature TYPE new_crypto_key_feature
+    USING (feature::text::new_crypto_key_feature);
+
+DROP TYPE crypto_key_feature;
+
+ALTER TYPE new_crypto_key_feature RENAME TO crypto_key_feature;
@@ -0,0 +1,40 @@
+INSERT INTO crypto_keys (feature, sequence, secret, secret_key_id, starts_at, deletes_at)
+VALUES (
+  'workspace_apps_token',
+  1,
+  'abc',
+  NULL,
+  '1970-01-01 00:00:00 UTC'::timestamptz,
+  '2100-01-01 00:00:00 UTC'::timestamptz
+);
+
+INSERT INTO crypto_keys (feature, sequence, secret, secret_key_id, starts_at, deletes_at)
+VALUES (
+  'workspace_apps_api_key',
+  1,
+  'def',
+  NULL,
+  '1970-01-01 00:00:00 UTC'::timestamptz,
+  '2100-01-01 00:00:00 UTC'::timestamptz
+);
+
+INSERT INTO crypto_keys (feature, sequence, secret, secret_key_id, starts_at, deletes_at)
+VALUES (
+  'oidc_convert',
+  2,
+  'ghi',
+  NULL,
+  '1970-01-01 00:00:00 UTC'::timestamptz,
+  '2100-01-01 00:00:00 UTC'::timestamptz
+);
+
+INSERT INTO crypto_keys (feature, sequence, secret, secret_key_id, starts_at, deletes_at)
+VALUES (
+  'tailnet_resume',
+  2,
+  'jkl',
+  NULL,
+  '1970-01-01 00:00:00 UTC'::timestamptz,
+  '2100-01-01 00:00:00 UTC'::timestamptz
+);
+