@@ -0,0 +1,16 @@
+---
+'@objectstack/cli': patch
+'@objectstack/service-settings': patch
+---
+
+fix(service-settings): when two data-key files hold different keys, the boot judges the newest stored secrets as a page, not only the newest one, and reports a database split between the two keys
+
+Clause-②: no — an internal boot heuristic and its notice text. The shapes it changes (`StoredSecretReader` now answers the page, `KeyFileChoice` gains the `mixed` reason and a `tally`, `DataKeyOpensNothingError` gains `judged`) were added by #30042, whose note is still pending, so they first ship together in this release; no released export changes.
+Metadata-protocol: none
+
+- **`@objectstack/service-settings`.** When the shared key file and the project's own key file hold different keys, the boot now trial-opens each of the newest stored `sys_secret` rows (up to ten) under both keys and reads with the key that opens more of them, on a tie the one that opens the newest. A row that opens under neither key (a corrupt or foreign row) no longer decides the boot: if an older row opens under one key, that key is used, and only a page where no row opens under either key keeps the production refusal. When each key opens some of the rows, the database holds secrets under both keys: the boot uses the key that opens more of them and prints an error naming both files, how many rows each key opened, and the fix. The boot's notices now say what was measured ("opens the 3 newest stored secrets", "opens 2 of the 3 newest stored secrets") instead of claiming the chosen file opens all of the database's stored secrets.
+- **`@objectstack/cli`.** The one-shot commands (`os migrate`, `os secret rewrap`, `os secret orphans`, `os storage orphans`) share the same trial, so they make the same choice.
+
+**The remedy for a split database.** Keep a copy of both files, then save again each secret that reads as unset: it is sealed under the key the boot uses. Once nothing reads as unset, put that key at the shared file (or set `OS_SECRET_KEY` to it).
+
+Supersedes, in the same release: the note for #30042 says the boot opens the newest stored secret under each key and quotes the refusal as "neither data key opens this database's stored secrets". After this change the boot judges the newest rows as a page, and the refusal reads "neither data key opens any of the N newest stored secrets".
@@ -29,6 +29,22 @@ Escrow the key in your secret manager the day you generate it, and treat
 key + database as one backup unit.
 </Callout>
 
+**Two key files on one host.** Without `OS_SECRET_KEY` (or `OS_DEV_CRYPTO_KEY`),
+the data key comes from a `dev-crypto-key` file: the canonical one under the
+ObjectStack home dir (`OS_HOME`, else `~/.objectstack`), which `os dev` and
+`os start` share, or a project's own `<project>/.objectstack/dev-crypto-key`,
+left by an earlier `os start`, when that is the only file holding a key. When
+both files exist and hold **different** keys, the boot trial-opens the newest
+stored secrets (up to ten rows) under each key once the database is open, uses
+the file whose key opens more of them, and prints which file it chose and how
+many rows each key opened. If each key opens some of the rows, the database
+holds secrets under both keys: the boot prints an error naming both files, and
+the secrets under the unused key read as unset until they are saved again. If
+neither key opens any of them, a production boot refuses to start and names
+both files. To converge on one key, keep a copy of both files, save again any
+secret that reads as unset, then put the key that opens them at the canonical
+path (or set `OS_SECRET_KEY` to it) and back that one key up with the database.
+
 ## Backing up the database
 
 Use the native tooling of whatever `OS_DATABASE_URL` points at — ObjectStack
 
@@ -5320,7 +5320,7 @@ export default class Serve extends Command {
           };
 
           // Fail-closed binder over the shared dev crypto provider. If the
-          // provider can't be created, leave `secrets` undefined — the plugin
+          // binder can't be built, leave `secrets` undefined — the plugin
           // then rejects secret-bearing create/update instead of storing
           // cleartext (by design).
           let secrets: any = undefined;
@@ -5341,12 +5341,14 @@ export default class Serve extends Command {
               cryptoProvider: sharedCryptoProvider,
             });
           } catch (cryptoErr: any) {
-            // Best-effort fail-closed: leave `secrets` undefined so the plugin
-            // rejects secret-bearing create/update rather than storing
-            // cleartext. A production deployment with no stable key still
-            // aborts boot loudly at the secret-field wiring below (where
-            // LocalCryptoProvider's "Refusing to start in production" error is
-            // rethrown), so we don't duplicate that abort here.
+            // Reached only when the module or the binder fails to load: the
+            // deferred provider constructs nothing here, so a key problem
+            // never lands in this catch. Leave `secrets` undefined so the
+            // plugin rejects secret-bearing create/update rather than storing
+            // cleartext. A key problem surfaces where the provider is first
+            // built, the secret-field wiring below (`resolve()`), which
+            // rethrows a production "Refusing to start in production" error,
+            // so the boot still refuses and nothing is duplicated here.
             console.warn(
               chalk.yellow(
                 `  ⚠ datasource admin: no CryptoProvider (${cryptoErr?.message ?? cryptoErr}); secret-bearing datasource create/update will fail closed`,
 
@@ -123,7 +123,7 @@ describe('#29934 — the key file an earlier `os start` kept in the project', ()
   ] as const)('%s: the child reads its secret back with the %s key', async (_shape, sealer) => {
     const keys = { legacy: writeKey(legacyFile()), canonical: writeKey(canonicalFile()) };
     const handle = await new LocalCryptoProvider({ key: keys[sealer] }).encrypt('sk-30042', ctx);
-    const stored = async () => ({ namespace: ctx.namespace, key: ctx.key, ciphertext: handle.ciphertext });
+    const stored = async () => [{ namespace: ctx.namespace, key: ctx.key, ciphertext: handle.ciphertext }];
     for (const { child } of [await startChild(), await devChild()]) {
       const quiet = vi.spyOn(console, 'warn').mockImplementation(() => {});
       // What the child's settings service does at start(), the database open.
 
@@ -255,7 +255,7 @@ describe('[#30042] one-shot commands take the same key file, by the same resolut
     // What the boot's settings service does at start(), the database open.
     await settleKeyFileChannel({
       env,
-      readStoredSecret: async () => ({ namespace: ctx.namespace, key: ctx.key, ciphertext: handle.ciphertext }),
+      readStoredSecret: async () => [{ namespace: ctx.namespace, key: ctx.key, ciphertext: handle.ciphertext }],
     });
     expect(await key.provider!.decrypt(handle, ctx)).toBe('sk-start');
     expect(key.provider!.keySource).toBe('file');
 
@@ -59,6 +59,12 @@ export interface ExistingDataKey {
 /**
  * Resolve the data key this host already has, never minting one. A key that
  * is missing, or set but unusable, is an answer here, not a throw.
+ *
+ * ⚠ It writes the key-file channels (`KEY_FILE_CHANNEL_ENV`,
+ * `KEY_FILE_CANDIDATE_CHANNEL_ENV`) on `opts.env`, which defaults to the real
+ * `process.env`: it sets or deletes both, so this process and every child it
+ * spawns afterwards read the file this call resolved. Pass an env map of your
+ * own to keep `process.env` untouched (the tests do).
  */
 export async function resolveExistingDataKey(
   opts: { cwd?: string; env?: NodeJS.ProcessEnv } = {},
@@ -77,11 +83,11 @@ export async function resolveExistingDataKey(
   // [#30042] The SAME file a `serve` child of `os dev` / `os start` reads for
   // this project, chosen by the same resolution: the canonical file, the
   // project's legacy file when it alone holds a key, and — when the two hold
-  // different keys — whichever opens a stored secret, ruled by the settings
-  // service in this run's own boot (`settleKeyFileChannel`). This process
-  // opens the database itself, so it is its own parent: it sets both channels
-  // on its own env, exactly as `applyCryptoKeyFileChannel` sets them on a
-  // child's.
+  // different keys — whichever opens more of the newest stored secrets, ruled
+  // by the settings service in this run's own boot (`settleKeyFileChannel`).
+  // This process opens the database itself, so it is its own parent: it sets
+  // both channels on its own env, exactly as `applyCryptoKeyFileChannel` sets
+  // them on a child's.
   const startHome = resolveStartHome(undefined, {
     hasProjectConfig: existsSync(path.resolve(cwd, 'objectstack.config.ts')),
     cwd,
 
@@ -52,9 +52,18 @@ The default is `LocalCryptoProvider` — AES-256-GCM keyed off a single
    across every restart and every node, or previously-encrypted secrets
    become undecryptable.
 2. `OS_DEV_CRYPTO_KEY` — dev convenience key (same format).
-3. A persisted file at `~/.objectstack/dev-crypto-key` (mode 0600). In
+3. A persisted file, `dev-crypto-key` (mode 0600) under `OS_HOME` (legacy
+   `OBJECTSTACK_HOME`, a leading `~` expanded), else `~/.objectstack`. In
    development this is auto-created so single-host dev loops survive
-   restarts; in production it is only *read*, never minted.
+   restarts; in production it is only *read*, never minted. Under the CLI
+   (`os dev`, `os start`, the one-shot commands) a project whose own
+   `.objectstack/dev-crypto-key` (left by an earlier `os start`) is the only
+   file holding a key reads that one instead. When both files hold
+   *different* keys, the boot trial-opens the newest stored `sys_secret`
+   rows (up to ten) under each key once the database is open, and reads the
+   file whose key opens more of them; a split between the two keys is a boot
+   error naming both files, and a production boot where neither key opens any
+   of them refuses to start (`DataKeyOpensNothingError`).
 
 **Fail-loud in production.** When `NODE_ENV=production` and no stable key
 source (env var or pre-existing file) is available, the provider refuses
 
@@ -38,7 +38,7 @@ export {
   type PersistedKeyFile,
   KEY_FILE_CHANNEL_ENV,
   // When those two files hold different keys, the process that opens the
-  // database rules between them by trial-opening a stored secret, or refuses.
+  // database rules between them by trial-opening its newest stored secrets, or refuses.
   KEY_FILE_CANDIDATE_CHANNEL_ENV,
   chooseKeyFileByTrialOpen,
   settleKeyFileChannel,
 
@@ -271,7 +271,8 @@ describe('#30042 — two key files: the boot takes the one that opens a stored s
     const h = await new LocalCryptoProvider({ key }).encrypt('sk-30042', { scope, namespace: 'ai', key: 'openai_api_key' });
     return { namespace: 'ai', key: 'openai_api_key', ciphertext: h.ciphertext };
   };
-  const reader = (sample: StoredSecretSample | undefined) => async () => sample;
+  /** A reader returning this page of stored rows, newest first. */
+  const reader = (...page: StoredSecretSample[]) => async () => page;
 
   it('the case-1 shape: a start-sealed database with a foreign home key reads with the legacy key', async () => {
     writeKey(canonical()); // `os dev` in another project minted this one
@@ -343,7 +344,7 @@ describe('#30042 — two key files: the boot takes the one that opens a stored s
   it('no stored secret: nothing to judge, the canonical file stands', async () => {
     writeKey(canonical());
     writeKey(legacy());
-    const choice = await chooseKeyFileByTrialOpen({ answer: bothDiffer(), readStoredSecret: reader(undefined), mode: 'production' });
+    const choice = await chooseKeyFileByTrialOpen({ answer: bothDiffer(), readStoredSecret: reader(), mode: 'production' });
     expect(choice).toMatchObject({ path: canonical(), reason: 'no-stored-secret' });
   });
 
@@ -362,8 +363,101 @@ describe('#30042 — two key files: the boot takes the one that opens a stored s
     expect(choice.notice?.message).toContain('connection reset');
   });
 
+  describe('#30091 — the trial scores both keys over the whole page, not its newest row', () => {
+    it.each(['production', 'development'] as const)(
+      '%s: rows split between the keys is a mixed-key boot ERROR naming both paths, on the key that opens more',
+      async (mode) => {
+        const canonicalKey = writeKey(canonical());
+        const legacyKey = writeKey(legacy());
+        // Newest first: the newest row is the canonical key's, the three older ones the legacy key's.
+        const page = [await sealed(canonicalKey), await sealed(legacyKey), await sealed(legacyKey), await sealed(legacyKey)];
+        const choice = await chooseKeyFileByTrialOpen({ answer: bothDiffer(), readStoredSecret: reader(...page), mode });
+        expect(choice).toMatchObject({
+          path: legacy(),
+          reason: 'mixed',
+          other: canonical(),
+          tally: { judged: 4, chosen: 3, other: 1 },
+        });
+        expect(choice.notice?.level).toBe('error');
+        expect(choice.notice?.message).toContain(canonical());
+        expect(choice.notice?.message).toContain(legacy());
+      },
+    );
+
+    it.each([
+      ['canonical', 'legacy'],
+      ['legacy', 'canonical'],
+    ] as const)('a tie goes to the key that opens the newest row (%s newest)', async (newest, older) => {
+      const keys = { canonical: writeKey(canonical()), legacy: writeKey(legacy()) };
+      const files = { canonical: canonical(), legacy: legacy() };
+      const choice = await chooseKeyFileByTrialOpen({
+        answer: bothDiffer(),
+        readStoredSecret: reader(await sealed(keys[newest]), await sealed(keys[older])),
+        mode: 'production',
+      });
+      expect(choice).toMatchObject({ path: files[newest], reason: 'mixed', tally: { judged: 2, chosen: 1, other: 1 } });
+    });
+
+    it('a corrupt newest row no longer refuses a production boot: an older row settles the choice', async () => {
+      writeKey(canonical());
+      const startKey = writeKey(legacy());
+      const corrupt = await sealed(randomBytes(32)); // opens under neither key
+      const choice = await chooseKeyFileByTrialOpen({
+        answer: bothDiffer(),
+        readStoredSecret: reader(corrupt, await sealed(startKey), await sealed(startKey, 'object_secret_field')),
+        mode: 'production',
+      });
+      expect(choice).toMatchObject({ path: legacy(), reason: 'opens', tally: { judged: 3, chosen: 2, other: 0 } });
+      expect(choice.notice?.level).toBe('warn');
+    });
+
+    it('one key opening every judged row is `opens`, with the count it was measured on', async () => {
+      const devKey = writeKey(canonical());
+      writeKey(legacy());
+      const choice = await chooseKeyFileByTrialOpen({
+        answer: bothDiffer(),
+        readStoredSecret: reader(await sealed(devKey), await sealed(devKey, 'datasource_credential')),
+        mode: 'production',
+      });
+      expect(choice).toMatchObject({ path: canonical(), reason: 'opens', tally: { judged: 2, chosen: 2, other: 0 } });
+    });
+
+    it('a page where no row opens under either key keeps the production refusal, counting the page', async () => {
+      writeKey(canonical());
+      writeKey(legacy());
+      const refusal = await chooseKeyFileByTrialOpen({
+        answer: bothDiffer(),
+        readStoredSecret: reader(await sealed(randomBytes(32)), await sealed(randomBytes(32))),
+        mode: 'production',
+      }).catch((e: unknown) => e);
+      expect(refusal).toBeInstanceOf(DataKeyOpensNothingError);
+      expect((refusal as DataKeyOpensNothingError).judged).toBe(2);
+      expect((refusal as Error).message).toContain('Refusing to start in production');
+    });
+
+    it('settleKeyFileChannel: a mixed page settles on the majority key and says so as console.error, once', async () => {
+      const canonicalKey = writeKey(canonical());
+      const legacyKey = writeKey(legacy());
+      const error = vi.spyOn(console, 'error').mockImplementation(() => {});
+      const warn = vi.spyOn(console, 'warn').mockImplementation(() => {});
+      const env: Record<string, string | undefined> = {
+        NODE_ENV: 'production',
+        [KEY_FILE_CHANNEL_ENV]: canonical(),
+        [KEY_FILE_CANDIDATE_CHANNEL_ENV]: legacy(),
+      };
+      const page = [await sealed(legacyKey), await sealed(canonicalKey), await sealed(canonicalKey)];
+      const choice = await settleKeyFileChannel({ env, readStoredSecret: reader(...page) });
+      expect(choice).toMatchObject({ path: canonical(), reason: 'mixed' });
+      expect(env[KEY_FILE_CHANNEL_ENV]).toBe(canonical());
+      expect(env[KEY_FILE_CANDIDATE_CHANNEL_ENV]).toBeUndefined();
+      expect(error).toHaveBeenCalledTimes(1);
+      expect(String(error.mock.calls[0]?.[0])).toContain(legacy());
+      expect(warn).not.toHaveBeenCalled();
+    });
+  });
+
   it('every one-file answer passes through untried', async () => {
-    const read = vi.fn(async () => undefined);
+    const read = vi.fn(async () => [] as StoredSecretSample[]);
     for (const answer of [
       { path: canonical(), kind: 'canonical', canonical: canonical() },
       { path: legacy(), kind: 'legacy-only', canonical: canonical(), legacy: legacy() },
@@ -431,7 +525,7 @@ describe('#30042 — two key files: the boot takes the one that opens a stored s
   });
 
   it('nothing to settle without a candidate', async () => {
-    const read = vi.fn(reader(undefined));
+    const read = vi.fn(reader());
     expect(await settleKeyFileChannel({ env: { [KEY_FILE_CHANNEL_ENV]: canonical() }, readStoredSecret: read })).toBeUndefined();
     expect(read).not.toHaveBeenCalled();
   });
@@ -460,12 +554,17 @@ describe('#30042 — two key files: the boot takes the one that opens a stored s
 
 describe('#30042 — the reader over the engine', () => {
   const v2 = 'v2:' + randomBytes(40).toString('base64');
-  it('reads the newest rows as the system and skips a marker the provider does not know', async () => {
+  it('reads the newest page as the system, keeps its order, and skips a marker the provider does not know', async () => {
+    const older = 'v2:' + randomBytes(40).toString('base64');
     const find = vi.fn(async () => [
       { namespace: 'x', key: 'y', ciphertext: 'v9:abc' },
       { namespace: 'ai', key: 'openai_api_key', ciphertext: v2 },
+      { namespace: 'mail', key: 'smtp_password', ciphertext: older },
+    ]);
+    expect(await storedSecretReaderOverEngine({ find })()).toEqual([
+      { namespace: 'ai', key: 'openai_api_key', ciphertext: v2 },
+      { namespace: 'mail', key: 'smtp_password', ciphertext: older },
     ]);
-    expect(await storedSecretReaderOverEngine({ find })()).toEqual({ namespace: 'ai', key: 'openai_api_key', ciphertext: v2 });
     expect(find).toHaveBeenCalledWith('sys_secret', expect.objectContaining({
       orderBy: [{ field: 'created_at', order: 'desc' }],
       context: { isSystem: true },
@@ -474,7 +573,7 @@ describe('#30042 — the reader over the engine', () => {
 
   it('a table that does not exist holds no row; any other failure rejects', async () => {
     const missing = storedSecretReaderOverEngine({ find: async () => { throw new Error('no such table: sys_secret'); } });
-    expect(await missing()).toBeUndefined();
+    expect(await missing()).toEqual([]);
     const broken = storedSecretReaderOverEngine({ find: async () => { throw new Error('connection reset'); } });
     await expect(broken()).rejects.toThrow('connection reset');
   });