@de-otio/chaoskb-client 0.3.6 → 0.3.7

package/dist/cli/bootstrap.d.ts

@@ -1,5 +1,11 @@
 export declare const CHAOSKB_DIR: string;
 export declare const FILE_KEY_PATH: string;
+/** OS keychain service name for chaoskb-managed slots. */
+export declare const KEYRING_SERVICE = "chaoskb";
+/** Fallback Ed25519 identity slot names. These live alongside the
+ *  personal master in the same service namespace. */
+export declare const IDENTITY_SECRET_SLOT = "identity-secret";
+export declare const IDENTITY_PUBLIC_SLOT = "identity-public";
 export interface BootstrapOptions {
     /** Override the base directory (default: ~/.chaoskb). For testing. */
     baseDir?: string;
@@ -7,9 +13,11 @@ export interface BootstrapOptions {
 /**
  * Auto-bootstrap ChaosKB on first launch.
  *
- * Creates ~/.chaoskb/, generates a master key, stores it in the OS keyring,
- * initializes the database, and writes config.json — all with standard
- * security tier and no interactive prompts.
+ * Creates ~/.chaoskb/, generates a master key, wraps it with the user's
+ * SSH public key (via keyring's `StandardTier`), persists the wrapped
+ * blob in the OS keychain, initializes the database, and writes
+ * config.json — all with standard security tier and no interactive
+ * prompts.
  *
  * Idempotent: no-ops if config.json already exists.
  * Concurrency-safe: uses file-based locking to prevent races.

package/dist/cli/bootstrap.d.ts.map

@@ -1 +1 @@
-{"version":3,"file":"bootstrap.d.ts","sourceRoot":"","sources":["../../cli/bootstrap.ts"],"names":[],"mappings":"AAMA,eAAO,MAAM,WAAW,QAAsC,CAAC;AAC/D,eAAO,MAAM,aAAa,QAAuC,CAAC;AAElE,MAAM,WAAW,gBAAgB;IAC/B,sEAAsE;IACtE,OAAO,CAAC,EAAE,MAAM,CAAC;CAClB;AAMD;;;;;;;;;GASG;AACH,wBAAsB,SAAS,CAAC,OAAO,CAAC,EAAE,gBAAgB,GAAG,OAAO,CAAC,IAAI,CAAC,CAsGzE;AA4XD;;;GAGG;AACH,wBAAsB,qBAAqB,CAAC,UAAU,EAAE,MAAM,GAAG,OAAO,CAAC,IAAI,CAAC,CAqB7E"}
+{"version":3,"file":"bootstrap.d.ts","sourceRoot":"","sources":["../../cli/bootstrap.ts"],"names":[],"mappings":"AAoBA,eAAO,MAAM,WAAW,QAAsC,CAAC;AAC/D,eAAO,MAAM,aAAa,QAAuC,CAAC;AAElE,0DAA0D;AAC1D,eAAO,MAAM,eAAe,YAAY,CAAC;AACzC;qDACqD;AACrD,eAAO,MAAM,oBAAoB,oBAAoB,CAAC;AACtD,eAAO,MAAM,oBAAoB,oBAAoB,CAAC;AAEtD,MAAM,WAAW,gBAAgB;IAC/B,sEAAsE;IACtE,OAAO,CAAC,EAAE,MAAM,CAAC;CAClB;AAsCD;;;;;;;;;;;GAWG;AACH,wBAAsB,SAAS,CAAC,OAAO,CAAC,EAAE,gBAAgB,GAAG,OAAO,CAAC,IAAI,CAAC,CA6IzE;AA8XD;;;GAGG;AACH,wBAAsB,qBAAqB,CAAC,UAAU,EAAE,MAAM,GAAG,OAAO,CAAC,IAAI,CAAC,CAsB7E"}

package/dist/cli/bootstrap.js

@@ -1,18 +1,57 @@
 import * as fs from 'node:fs';
 import * as path from 'node:path';
 import * as os from 'node:os';
+import { randomBytes } from 'node:crypto';
+import { KeyRing, StandardTier, OsKeychainStorage, FileSystemStorage, OsKeychainUnavailable, parseSshPublicKey, } from '@de-otio/keyring';
+import { SecureBuffer, asMasterKey } from '@de-otio/crypto-envelope';
 import { acquireBootstrapLock } from './bootstrap-lock.js';
 export const CHAOSKB_DIR = path.join(os.homedir(), '.chaoskb');
 export const FILE_KEY_PATH = path.join(CHAOSKB_DIR, 'master.key');
+/** OS keychain service name for chaoskb-managed slots. */
+export const KEYRING_SERVICE = 'chaoskb';
+/** Fallback Ed25519 identity slot names. These live alongside the
+ *  personal master in the same service namespace. */
+export const IDENTITY_SECRET_SLOT = 'identity-secret';
+export const IDENTITY_PUBLIC_SLOT = 'identity-public';
 function resolveDir(baseDir) {
     return baseDir ?? CHAOSKB_DIR;
 }
+/**
+ * Build the chaoskb keyring storage. Prefers the OS keychain; falls back
+ * to a filesystem store when `CHAOSKB_KEY_STORAGE=file` is set or the OS
+ * keychain is unavailable (headless CI, unsupported platform).
+ *
+ * The filesystem fallback mirrors the previous `master.key` location but
+ * uses keyring's `FileSystemStorage` format — slot files under a 0700
+ * directory. Wire format is v1 per keyring.
+ */
+async function buildStorage(baseDir) {
+    const wantFile = process.env.CHAOSKB_KEY_STORAGE === 'file';
+    if (wantFile) {
+        const fsDir = path.join(baseDir, 'keyring');
+        fs.mkdirSync(fsDir, { recursive: true, mode: 0o700 });
+        return {
+            storage: new FileSystemStorage({ root: fsDir }),
+            kind: 'file',
+        };
+    }
+    // OS keychain is checked lazily when the first put/get/delete is made.
+    return {
+        storage: new OsKeychainStorage({
+            service: KEYRING_SERVICE,
+            acceptedTiers: ['standard'],
+        }),
+        kind: 'os-keychain',
+    };
+}
 /**
  * Auto-bootstrap ChaosKB on first launch.
  *
- * Creates ~/.chaoskb/, generates a master key, stores it in the OS keyring,
- * initializes the database, and writes config.json — all with standard
- * security tier and no interactive prompts.
+ * Creates ~/.chaoskb/, generates a master key, wraps it with the user's
+ * SSH public key (via keyring's `StandardTier`), persists the wrapped
+ * blob in the OS keychain, initializes the database, and writes
+ * config.json — all with standard security tier and no interactive
+ * prompts.
  *
  * Idempotent: no-ops if config.json already exists.
  * Concurrency-safe: uses file-based locking to prevent races.
@@ -21,7 +60,6 @@ export async function bootstrap(options) {
     const chaoskbDir = resolveDir(options?.baseDir);
     const configPath = path.join(chaoskbDir, 'config.json');
     const modelsDir = path.join(chaoskbDir, 'models');
-    const fileKeyPath = path.join(chaoskbDir, 'master.key');
     // Fast path: already configured
     if (fs.existsSync(configPath)) {
         return;
@@ -40,44 +78,78 @@ export async function bootstrap(options) {
         if (!fs.existsSync(modelsDir)) {
             fs.mkdirSync(modelsDir, { recursive: true, mode: 0o700 });
         }
-        // 2. Generate master key
-        const { EncryptionService } = await import('../crypto/encryption-service.js');
-        const encryption = new EncryptionService();
-        const masterKey = encryption.generateMasterKey();
-        // 3. Store master key
+        // 2. Detect SSH key for zero-config sync and as the keyring tier input.
+        const sshResult = await detectSSHKey(chaoskbDir);
+        // 3. Generate a random 32-byte master key (plain Uint8Array — we hand
+        //    it to keyring which owns its SecureBuffer lifecycle).
+        const masterBytes = new Uint8Array(randomBytes(32));
+        const masterSb = SecureBuffer.from(Buffer.from(masterBytes));
+        const master = asMasterKey(masterSb);
+        // Keep a copy for sync registration (pre-upload). Zeroed at the end.
+        const masterKeyCopy = Buffer.from(masterBytes);
+        masterBytes.fill(0);
+        // 4. Wrap the master with the SSH key and persist via keyring.
+        let keyringOk = false;
         try {
-            await storeKeyInKeyring(masterKey);
+            if (sshResult.publicKey) {
+                const tier = StandardTier.fromSshKey(sshResult.publicKey);
+                const { storage } = await buildStorage(chaoskbDir);
+                const ring = new KeyRing({ tier, storage });
+                await ring.setup(master);
+                keyringOk = true;
+                if (process.platform === 'darwin') {
+                    process.stderr.write('Storing encryption key in macOS Keychain.\n' +
+                        'You may see a system dialog asking to allow keychain access — this is expected.\n');
+                }
+            }
         }
         catch (keyringError) {
-            // Keyring failed — check for file-based fallback
-            if (process.env.CHAOSKB_KEY_STORAGE === 'file') {
-                process.stderr.write('\n⚠ OS keyring unavailable. Storing key in ' + fileKeyPath + ' (file-based).\n' +
+            // Master not yet disposed — fall through to file fallback.
+            if (process.env.CHAOSKB_KEY_STORAGE === 'file' || keyringError instanceof OsKeychainUnavailable) {
+                process.stderr.write('\n⚠ OS keyring unavailable. Storing key in ' +
+                    FILE_KEY_PATH +
+                    ' (file-based).\n' +
                     '  This is less secure than the OS keyring. The key file is readable by any process running as your user.\n\n');
-                fs.writeFileSync(fileKeyPath, masterKey.buffer.toString('hex'), { mode: 0o600 });
+                fs.writeFileSync(path.join(chaoskbDir, 'master.key'), masterKeyCopy.toString('hex'), {
+                    mode: 0o600,
+                });
+                keyringOk = true;
             }
             else {
-                masterKey.dispose();
+                master.dispose();
+                masterKeyCopy.fill(0);
                 throw new Error(`Failed to store master key in OS keyring: ${keyringError instanceof Error ? keyringError.message : String(keyringError)}\n\n` +
                     '  To fix this, either:\n' +
                     '  • Install/configure your OS keyring service (macOS Keychain, Linux Secret Service, Windows Credential Manager)\n' +
                     '  • Set CHAOSKB_KEY_STORAGE=file to use file-based key storage (less secure)\n');
             }
         }
-        // Copy master key bytes before disposing (needed for sync registration)
-        const masterKeyBytes = Buffer.from(masterKey.buffer);
-        masterKey.dispose();
-        // 4. Initialize database
+        if (!keyringOk && !sshResult.publicKey) {
+            // No SSH key at all AND we didn't persist yet — fall back to file
+            // storage so the bootstrap can still complete.
+            if (process.env.CHAOSKB_KEY_STORAGE === 'file') {
+                fs.writeFileSync(path.join(chaoskbDir, 'master.key'), masterKeyCopy.toString('hex'), {
+                    mode: 0o600,
+                });
+            }
+            else {
+                master.dispose();
+                masterKeyCopy.fill(0);
+                throw new Error('No SSH key found and CHAOSKB_KEY_STORAGE=file not set. ' +
+                    'Run `ssh-keygen` or set CHAOSKB_KEY_STORAGE=file to continue.');
+            }
+        }
+        master.dispose();
+        // 5. Initialize database
         const { DatabaseManager } = await import('../storage/database-manager.js');
         const dbManager = new DatabaseManager(chaoskbDir);
         const db = dbManager.getPersonalDb();
         db.close();
         dbManager.closeAll();
-        // 5. Detect SSH key for zero-config sync
-        const sshResult = await detectSSHKey();
         // 6. Register with sync server (non-blocking)
-        const syncResult = await attemptSyncRegistration(sshResult, masterKeyBytes);
+        const syncResult = await attemptSyncRegistration(sshResult, masterKeyCopy, chaoskbDir);
         // Zero the copy
-        masterKeyBytes.fill(0);
+        masterKeyCopy.fill(0);
         // 7. Write config
         const config = {
             securityTier: 'standard',
@@ -112,7 +184,7 @@ export async function bootstrap(options) {
  * Priority: ssh-agent (Ed25519 > RSA) → filesystem (id_ed25519 > id_rsa)
  * If no SSH key found, returns source: 'none'.
  */
-async function detectSSHKey() {
+async function detectSSHKey(baseDir) {
     // Respect opt-out
     if (process.env.CHAOSKB_SYNC === 'off') {
         return { publicKey: null, fingerprint: null, keyPath: null, source: 'none' };
@@ -150,8 +222,7 @@ async function detectSSHKey() {
         if (fs.existsSync(pubKeyPath)) {
             try {
                 const content = fs.readFileSync(pubKeyPath, 'utf-8').trim();
-                const { parseSSHPublicKey } = await import('../crypto/ssh-keys.js');
-                const parsed = parseSSHPublicKey(content);
+                const parsed = parseSshPublicKey(content);
                 return {
                     publicKey: content,
                     fingerprint: parsed.fingerprint,
@@ -167,7 +238,7 @@ async function detectSSHKey() {
     }
     // No SSH key found — try generating a fallback key in keyring
     try {
-        const fallback = await generateFallbackKey();
+        const fallback = await generateFallbackKey(baseDir);
         if (fallback)
             return fallback;
     }
@@ -179,19 +250,40 @@ async function detectSSHKey() {
 /**
  * Generate a fallback Ed25519 key pair and store it in the OS keyring.
  * Never written to disk. Returns null if keyring is unavailable.
+ *
+ * Uses keyring's `OsKeychainStorage` directly at dedicated slot names.
+ * Stored as a degenerate `WrappedKey` shape — the slot contract is a
+ * `WrappedKey`, so we wrap the raw identity bytes in the `envelope`
+ * field and use tier='standard' purely as a placeholder. This is a
+ * chaoskb-specific convention; the bytes are not AEAD-wrapped because
+ * the whole point is that there's no other key material to wrap them
+ * with on a new install.
  */
-async function generateFallbackKey() {
+async function generateFallbackKey(_baseDir) {
     const sodium = (await import('sodium-native')).default;
-    const { KeyringService } = await import('../crypto/keyring.js');
     const pk = Buffer.alloc(sodium.crypto_sign_PUBLICKEYBYTES);
     const sk = Buffer.alloc(sodium.crypto_sign_SECRETKEYBYTES);
     sodium.crypto_sign_keypair(pk, sk);
     try {
-        // Store secret key in keyring only (never on disk)
-        const keyring = new KeyringService();
-        const { SecureBuffer } = await import('../crypto/secure-buffer.js');
-        await keyring.store('chaoskb', 'identity-secret', SecureBuffer.from(sk));
-        await keyring.store('chaoskb', 'identity-public', SecureBuffer.from(pk));
+        const storage = new OsKeychainStorage({
+            service: KEYRING_SERVICE,
+            acceptedTiers: ['standard'],
+        });
+        const now = new Date().toISOString();
+        const skWrapped = {
+            v: 1,
+            tier: 'standard',
+            envelope: new Uint8Array(sk),
+            ts: now,
+        };
+        const pkWrapped = {
+            v: 1,
+            tier: 'standard',
+            envelope: new Uint8Array(pk),
+            ts: now,
+        };
+        await storage.put(IDENTITY_SECRET_SLOT, skWrapped);
+        await storage.put(IDENTITY_PUBLIC_SLOT, pkWrapped);
     }
     catch {
         sk.fill(0);
@@ -200,10 +292,7 @@ async function generateFallbackKey() {
     // Build the SSH public key line
     const { createHash } = await import('node:crypto');
     const typeStr = Buffer.from('ssh-ed25519');
-    const keyBlob = Buffer.concat([
-        uint32BE(typeStr.length), typeStr,
-        uint32BE(pk.length), pk,
-    ]);
+    const keyBlob = Buffer.concat([uint32BE(typeStr.length), typeStr, uint32BE(pk.length), pk]);
     const base64Blob = keyBlob.toString('base64');
     const fingerprint = 'SHA256:' + createHash('sha256').update(keyBlob).digest('base64').replace(/=+$/, '');
     sk.fill(0);
@@ -226,7 +315,7 @@ const DEFAULT_SYNC_ENDPOINT = 'https://sync.chaoskb.com';
  * Non-blocking: if the server is unreachable, returns pending=true
  * and the next launch will retry.
  */
-async function attemptSyncRegistration(ssh, masterKeyBuffer) {
+async function attemptSyncRegistration(ssh, masterKeyBuffer, baseDir) {
     if (process.env.CHAOSKB_SYNC === 'off' || !ssh.publicKey) {
         return { enabled: false, pending: false, endpoint: null };
     }
@@ -243,7 +332,7 @@ async function attemptSyncRegistration(ssh, masterKeyBuffer) {
         if (!challengeRes.ok) {
             return { enabled: false, pending: true, endpoint };
         }
-        const { challenge } = await challengeRes.json();
+        const { challenge } = (await challengeRes.json());
         // Step 2: Sign the challenge using SSHSigner (handles OpenSSH key formats + ssh-agent)
         const { SSHSigner } = await import('../sync/ssh-signer.js');
         const signer = new SSHSigner(ssh.keyPath ?? undefined);
@@ -275,15 +364,15 @@ async function attemptSyncRegistration(ssh, masterKeyBuffer) {
             // Other server errors — mark as pending for retry
             return { enabled: false, pending: true, endpoint };
         }
-        const regResult = await response.json();
-        // Existing account — download and unwrap master key (new-device restore)
+        const regResult = (await response.json());
+        // Existing account — download and store the server's wrapped master.
         if (regResult.status === 'existing') {
-            await restoreMasterKey(endpoint, ssh);
+            await restoreMasterKey(endpoint, ssh, baseDir);
             return { enabled: true, pending: false, endpoint };
         }
         // New account — wrap master key and upload
         if (masterKeyBuffer.length > 0) {
-            await uploadWrappedMasterKey(endpoint, ssh, masterKeyBuffer);
+            await uploadWrappedMasterKey(endpoint, ssh, masterKeyBuffer, baseDir);
         }
         return { enabled: true, pending: false, endpoint };
     }
@@ -306,19 +395,20 @@ async function fetchWithTimeout(url, init) {
     }
 }
 /**
- * Wrap the master key with the SSH public key and upload to the sync server.
- * The wrapped blob is signed with the SSH private key for integrity verification.
+ * Wrap the master key with the SSH public key and upload to the sync
+ * server. Uses keyring's `StandardTier.wrap` so the wire format is v1.
  */
-async function uploadWrappedMasterKey(endpoint, ssh, masterKeyBuffer) {
+async function uploadWrappedMasterKey(endpoint, ssh, masterKeyBuffer, _baseDir) {
     if (!ssh.publicKey)
         return;
-    const { parseSSHPublicKey } = await import('../crypto/ssh-keys.js');
-    const { wrapMasterKey } = await import('../crypto/tiers/standard.js');
-    const { SecureBuffer } = await import('../crypto/secure-buffer.js');
-    const keyInfo = parseSSHPublicKey(ssh.publicKey);
-    const secureMasterKey = SecureBuffer.from(masterKeyBuffer);
+    const tier = StandardTier.fromSshKey(ssh.publicKey);
+    const masterSb = SecureBuffer.from(Buffer.from(masterKeyBuffer));
+    const master = asMasterKey(masterSb);
     try {
-        const wrappedBlob = wrapMasterKey(secureMasterKey, keyInfo);
+        const wrapped = await tier.wrap(master);
+        // Wire format: raw `WrappedKey.envelope` bytes. The server stores
+        // them opaquely — only the client (which has the SSH private key) can
+        // unwrap them.
         const { createSyncHttpClientFromConfig } = await import('../sync/client-factory.js');
         const { DatabaseManager } = await import('../storage/database-manager.js');
         const db = new DatabaseManager().getPersonalDb();
@@ -326,20 +416,23 @@ async function uploadWrappedMasterKey(endpoint, ssh, masterKeyBuffer) {
             endpoint,
             sshKeyPath: ssh.keyPath ?? undefined,
         }, db.syncSequence);
-        await client.put('/v1/wrapped-key', wrappedBlob);
+        await client.put('/v1/wrapped-key', wrapped.envelope);
     }
     finally {
-        secureMasterKey.dispose();
+        master.dispose();
     }
 }
 /**
  * Restore the master key on a new device.
  *
- * Downloads the wrapped master key blob from the server,
- * verifies the signature, unwraps with the SSH private key,
- * and stores in the OS keyring.
+ * Downloads the wrapped master-key blob from the server and persists it
+ * verbatim into keyring storage at the `__personal` slot. We also attempt
+ * an `unlockWithSshKey` to verify the bytes are usable with the local SSH
+ * private key; the unwrapped master is immediately discarded — the
+ * keyring stays in its wrapped form on disk, to be unlocked on demand by
+ * `initializeDependencies`.
  */
-async function restoreMasterKey(endpoint, ssh) {
+async function restoreMasterKey(endpoint, ssh, baseDir) {
     if (!ssh.publicKey)
         return;
     const { createSyncHttpClientFromConfig } = await import('../sync/client-factory.js');
@@ -353,63 +446,34 @@ async function restoreMasterKey(endpoint, ssh) {
     if (!response.ok) {
         throw new Error(`Failed to download wrapped key: ${response.status}`);
     }
-    const wrappedBlob = new Uint8Array(await response.arrayBuffer());
-    // Unwrap with SSH private key
-    const { parseSSHPublicKey } = await import('../crypto/ssh-keys.js');
-    const keyInfo = parseSSHPublicKey(ssh.publicKey);
-    if (keyInfo.type === 'ed25519') {
-        const { unwrapMasterKeyEd25519 } = await import('../crypto/tiers/standard.js');
-        // Read the private key to get the secret key bytes for unwrapping
-        // For Ed25519 unwrap, we need the raw secret key — ssh-agent can sign
-        // but can't expose the raw key for crypto_box_seal_open.
-        // Fall back to key file for unwrapping.
-        if (ssh.keyPath) {
-            const keyData = fs.readFileSync(ssh.keyPath, 'utf-8');
-            const { createPrivateKey } = await import('node:crypto');
-            const keyObj = createPrivateKey({ key: keyData, format: 'pem' });
-            const exported = keyObj.export({ type: 'pkcs8', format: 'der' });
-            // Ed25519 PKCS8 DER: last 32 bytes are the private key, preceded by 2-byte wrapper
-            // The actual key bytes are at offset 16 (after DER headers), 32 bytes of seed + 32 bytes of public
-            const derBuf = Buffer.from(exported);
-            // Extract the 32-byte seed from the PKCS8 structure
-            // PKCS8 for Ed25519: 30 2e 02 01 00 30 05 06 03 2b 65 70 04 22 04 20 [32 bytes seed]
-            const seedOffset = derBuf.indexOf(Buffer.from([0x04, 0x20]), 12);
-            if (seedOffset === -1) {
-                throw new Error('Could not extract Ed25519 seed from private key');
-            }
-            const seed = derBuf.subarray(seedOffset + 2, seedOffset + 34);
-            // Generate the full 64-byte secret key from the seed
-            const sodium = (await import('sodium-native')).default;
-            const fullSk = Buffer.alloc(sodium.crypto_sign_SECRETKEYBYTES);
-            const fullPk = Buffer.alloc(sodium.crypto_sign_PUBLICKEYBYTES);
-            sodium.crypto_sign_seed_keypair(fullPk, fullSk, seed);
-            const masterKey = unwrapMasterKeyEd25519(wrappedBlob, fullSk, fullPk);
-            // Store in keyring
-            await storeKeyInKeyring(masterKey);
-            masterKey.dispose();
-            // Zero sensitive buffers
-            fullSk.fill(0);
-            seed.fill(0);
-        }
-        else {
-            // Key is in agent only — can't extract raw key for crypto_box_seal_open
-            // This is a known limitation: agent-only keys can sign but can't unwrap sealed boxes
-            throw new Error('Cannot restore master key: SSH key is in agent only (no key file).\n' +
-                'crypto_box_seal_open requires the raw private key. Ensure the key file is available at ~/.ssh/id_ed25519');
+    const wrappedEnvelopeBytes = new Uint8Array(await response.arrayBuffer());
+    // Persist to keyring storage as a v1 WrappedKey.
+    const wrapped = {
+        v: 1,
+        tier: 'standard',
+        envelope: wrappedEnvelopeBytes,
+        sshFingerprint: ssh.fingerprint ?? undefined,
+        ts: new Date().toISOString(),
+    };
+    const { storage } = await buildStorage(baseDir);
+    await storage.put('__personal', wrapped);
+    // Verify it's unwrappable with the local SSH key (non-fatal: if the key
+    // file is missing, the unlock below will just skip and the unwrap will
+    // happen lazily on first MCP tool use).
+    if (ssh.keyPath) {
+        try {
+            const pem = fs.readFileSync(ssh.keyPath, 'utf-8');
+            const tier = StandardTier.fromSshKey(ssh.publicKey);
+            const ring = new KeyRing({ tier, storage });
+            await ring.unlockWithSshKey(pem);
+            await ring.lock();
         }
-    }
-    else {
-        // RSA unwrap
-        const { unwrapMasterKeyRSA } = await import('../crypto/tiers/standard.js');
-        const { createPrivateKey } = await import('node:crypto');
-        if (!ssh.keyPath) {
-            throw new Error('Cannot restore master key: no RSA key file path');
+        catch (err) {
+            // Verification failed — surface a diagnostic but leave the blob
+            // in place. Unlock failure now is unusual but not catastrophic;
+            // the MCP server will retry on tool-call time.
+            process.stderr.write(`Warning: downloaded wrapped key failed verify-unlock: ${err instanceof Error ? err.message : String(err)}\n`);
         }
-        const keyData = fs.readFileSync(ssh.keyPath, 'utf-8');
-        const rsaPrivKey = createPrivateKey({ key: keyData, format: 'pem' });
-        const masterKey = unwrapMasterKeyRSA(wrappedBlob, rsaPrivKey);
-        await storeKeyInKeyring(masterKey);
-        masterKey.dispose();
     }
     process.stderr.write('Master key restored from sync server. Your knowledge base will sync shortly.\n');
 }
@@ -422,10 +486,11 @@ export async function retrySyncRegistration(configPath) {
         const configData = JSON.parse(fs.readFileSync(configPath, 'utf-8'));
         if (!configData.syncPending)
             return;
-        const sshResult = await detectSSHKey();
+        const baseDir = path.dirname(configPath);
+        const sshResult = await detectSSHKey(baseDir);
         if (!sshResult.publicKey)
             return;
-        const syncResult = await attemptSyncRegistration(sshResult, Buffer.alloc(0));
+        const syncResult = await attemptSyncRegistration(sshResult, Buffer.alloc(0), baseDir);
         if (syncResult.enabled || !syncResult.pending) {
             // Either succeeded or permanently failed — clear pending
             configData.syncEnabled = syncResult.enabled;
@@ -441,14 +506,4 @@ export async function retrySyncRegistration(configPath) {
         // Retry failed silently — will try again next launch
     }
 }
-async function storeKeyInKeyring(masterKey) {
-    // macOS: warn about potential keychain access dialog
-    if (process.platform === 'darwin') {
-        process.stderr.write('Storing encryption key in macOS Keychain.\n' +
-            'You may see a system dialog asking to allow keychain access — this is expected.\n');
-    }
-    const { KeyringService } = await import('../crypto/keyring.js');
-    const keyring = new KeyringService();
-    await keyring.store('chaoskb', 'master-key', masterKey);
-}
 //# sourceMappingURL=bootstrap.js.map

package/dist/cli/bootstrap.js.map

@@ -1 +1 @@
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package/dist/cli/commands/config.d.ts

@@ -1,13 +1,16 @@
+import { type WrappedKey } from '@de-otio/keyring';
 /**
  * Upgrade security tier.
  *
- * Standard → Maximum: re-wrap master key under Argon2id-derived key from passphrase.
- * Enhanced → Maximum: same as above, with note that mnemonic is invalidated.
+ * Standard → Maximum: unlock master via the current Standard tier,
+ * then re-wrap under a passphrase-derived KEK via keyring's `MaximumTier`.
  *
- * Note: The Enhanced tier (BIP39 mnemonic) is deprecated. New upgrades only
- * support "maximum". Existing Enhanced-tier users can still upgrade to Maximum.
+ * Note: The Enhanced tier (BIP39 mnemonic) is deprecated. New upgrades
+ * only support "maximum".
  */
 export declare function upgradeTierCommand(tier: string, options?: {
     dryRun?: boolean;
 }): Promise<void>;
+/** Parse the serialised form back into a WrappedKey. */
+export declare function parseWrappedKey(json: string): WrappedKey;
 //# sourceMappingURL=config.d.ts.map

package/dist/cli/commands/config.d.ts.map

@@ -1 +1 @@
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