@tyvm/knowhow 0.0.151 → 0.0.153

package/package.json

@@ -1,6 +1,6 @@
 {
   "name": "@tyvm/knowhow",
-  "version": "0.0.151",
+  "version": "0.0.153",
   "description": "ai cli with plugins and agents",
   "main": "ts_build/src/index.js",
   "bin": {

package/src/auth/keyManager.ts

@@ -6,6 +6,13 @@ import path from "path";
 const ED25519_KEY_TYPE = "ssh-ed25519";
 const ED25519_RAW_KEY_LENGTH = 32;
 const ED25519_SPKI_PREFIX = Buffer.from("302a300506032b6570032100", "hex");
+const ED25519_PKCS8_PREFIX = Buffer.from("302e020100300506032b657004220420", "hex");
+
+interface OpenSshMetadata {
+  encrypted: boolean;
+  algorithm?: string;
+  seed?: Buffer;
+}
 
 export interface KeyPair {
   privateKeyPath: string;
@@ -90,6 +97,14 @@ export function getOrCreatePublicKey(privateKeyPath?: string): KeyPair {
     : generateKeyPair(privateKeyPath);
 }
 
+export function ensureIdentityKeyPair(privateKeyPath?: string): {
+  keyPair: KeyPair;
+  created: boolean;
+} {
+  if (keyPairExists(privateKeyPath)) return { keyPair: loadKeyPair(privateKeyPath), created: false };
+  return { keyPair: generateKeyPair(privateKeyPath), created: true };
+}
+
 export function signMessage(message: string, privateKeyPath?: string): string {
   const privatePath = privateKeyPath ?? getDefaultPrivateKeyPath();
   if (!fs.existsSync(privatePath)) throw new Error(`Private key not found at: ${privatePath}`);
@@ -98,14 +113,50 @@ export function signMessage(message: string, privateKeyPath?: string): string {
 
 function readEd25519PrivateKey(privatePath: string): crypto.KeyObject {
   let key: crypto.KeyObject;
+  const privateKeyContents = fs.readFileSync(privatePath, "utf8");
+  const openSshMetadata = parseOpenSshMetadata(privateKeyContents);
+
+  if (openSshMetadata?.encrypted) {
+    throw new Error(
+      `Identity at ${privatePath} is an encrypted OpenSSH key. Use an unencrypted Ed25519 key for CLI auth (example: ssh-keygen -t ed25519 -N '' -f ${privatePath})`
+    );
+  }
+
   try {
-    key = crypto.createPrivateKey(fs.readFileSync(privatePath));
+    key = crypto.createPrivateKey({ key: privateKeyContents, format: "pem" });
   } catch {
-    throw new Error(`Identity at ${privatePath} is not a supported PEM Ed25519 private key`);
+    if (openSshMetadata) {
+      if (openSshMetadata.algorithm && openSshMetadata.algorithm !== ED25519_KEY_TYPE) {
+        throw new Error(
+          `Identity at ${privatePath} must be an OpenSSH Ed25519 key (found ${openSshMetadata.algorithm})`
+        );
+      }
+
+      if (openSshMetadata.seed) {
+        key = createEd25519PrivateKeyFromSeed(openSshMetadata.seed, privatePath);
+      } else {
+        throw new Error(
+          `Identity at ${privatePath} must be a PKCS#8 Ed25519 private key or an unencrypted OpenSSH Ed25519 private key`
+        );
+      }
+      return key;
+    }
+
+    throw new Error(`Identity at ${privatePath} must be a PKCS#8 Ed25519 private key or an unencrypted OpenSSH Ed25519 private key`);
   }
+
+  const detectedAlgorithm = key.asymmetricKeyType === "ed25519" ? openSshMetadata?.algorithm ?? "ed25519" : key.asymmetricKeyType;
+
   if (key.asymmetricKeyType !== "ed25519") {
-    throw new Error(`Identity at ${privatePath} must be an Ed25519 private key`);
+    throw new Error(
+      `Identity at ${privatePath} must be an Ed25519 private key (found ${detectedAlgorithm ?? "unknown"})`
+    );
+  }
+
+  if (openSshMetadata?.algorithm && openSshMetadata.algorithm !== ED25519_KEY_TYPE) {
+    throw new Error(`Identity at ${privatePath} must be an OpenSSH Ed25519 key (found ${openSshMetadata.algorithm})`);
   }
+
   return key;
 }
 
@@ -164,3 +215,117 @@ function keyPairMetadata(privatePath: string, rawPublicKey: Buffer): KeyPair {
     fingerprint: `SHA256:${hash}`,
   };
 }
+
+function createEd25519PrivateKeyFromSeed(seed: Buffer, privatePath: string): crypto.KeyObject {
+  if (seed.length !== ED25519_RAW_KEY_LENGTH) {
+    throw new Error(`Identity at ${privatePath} has an invalid OpenSSH Ed25519 private key payload`);
+  }
+
+  try {
+    const der = Buffer.concat([ED25519_PKCS8_PREFIX, seed]);
+    return crypto.createPrivateKey({ key: der, format: "der", type: "pkcs8" });
+  } catch {
+    throw new Error(
+      `Identity at ${privatePath} must be a PKCS#8 Ed25519 private key or an unencrypted OpenSSH Ed25519 private key`
+    );
+  }
+}
+
+function parseOpenSshMetadata(privateKeyContents: string): OpenSshMetadata | undefined {
+  const trimmed = privateKeyContents.trim();
+  if (!trimmed.startsWith("-----BEGIN OPENSSH PRIVATE KEY-----")) {
+    return undefined;
+  }
+
+  const body = trimmed
+    .replace("-----BEGIN OPENSSH PRIVATE KEY-----", "")
+    .replace("-----END OPENSSH PRIVATE KEY-----", "")
+    .replace(/\s+/g, "");
+
+  let buffer: Buffer;
+  try {
+    buffer = Buffer.from(body, "base64");
+  } catch {
+    return undefined;
+  }
+
+  let offset = 0;
+
+  const magic = Buffer.from("openssh-key-v1\0", "utf8");
+  if (buffer.length < magic.length || !buffer.subarray(0, magic.length).equals(magic)) {
+    return undefined;
+  }
+  offset += magic.length;
+
+  const readString = (): string | undefined => {
+    if (offset + 4 > buffer.length) return undefined;
+    const length = buffer.readUInt32BE(offset);
+    offset += 4;
+    if (offset + length > buffer.length) return undefined;
+    const value = buffer.subarray(offset, offset + length).toString("utf8");
+    offset += length;
+    return value;
+  };
+
+  const readBuffer = (): Buffer | undefined => {
+    if (offset + 4 > buffer.length) return undefined;
+    const length = buffer.readUInt32BE(offset);
+    offset += 4;
+    if (offset + length > buffer.length) return undefined;
+    const value = buffer.subarray(offset, offset + length);
+    offset += length;
+    return value;
+  };
+
+  const ciphername = readString();
+  const kdfname = readString();
+  const kdfoptions = readBuffer();
+  if (!ciphername || !kdfname || !kdfoptions) {
+    return undefined;
+  }
+
+  if (offset + 4 > buffer.length) return { encrypted: ciphername !== "none" || kdfname !== "none" };
+  const keyCount = buffer.readUInt32BE(offset);
+  offset += 4;
+
+  for (let i = 0; i < keyCount; i++) {
+    const skippedPublic = readBuffer();
+    if (!skippedPublic) return { encrypted: ciphername !== "none" || kdfname !== "none" };
+  }
+
+  const privateBlock = readBuffer();
+  if (!privateBlock) return { encrypted: ciphername !== "none" || kdfname !== "none" };
+
+  let privateOffset = 0;
+  const readPrivateString = (): string | undefined => {
+    if (privateOffset + 4 > privateBlock.length) return undefined;
+    const length = privateBlock.readUInt32BE(privateOffset);
+    privateOffset += 4;
+    if (privateOffset + length > privateBlock.length) return undefined;
+    const value = privateBlock.subarray(privateOffset, privateOffset + length).toString("utf8");
+    privateOffset += length;
+    return value;
+  };
+
+  const readPrivateBuffer = (): Buffer | undefined => {
+    if (privateOffset + 4 > privateBlock.length) return undefined;
+    const length = privateBlock.readUInt32BE(privateOffset);
+    privateOffset += 4;
+    if (privateOffset + length > privateBlock.length) return undefined;
+    const value = privateBlock.subarray(privateOffset, privateOffset + length);
+    privateOffset += length;
+    return value;
+  };
+
+  privateOffset += 8; // checkints
+
+  const algorithm = readPrivateString();
+  let seed: Buffer | undefined;
+  if (algorithm === ED25519_KEY_TYPE) {
+    readPrivateBuffer(); // public key (32 bytes)
+    const privateConcat = readPrivateBuffer(); // private seed (32) + public key (32)
+    seed = privateConcat?.subarray(0, ED25519_RAW_KEY_LENGTH);
+  }
+
+  return { encrypted: ciphername !== "none" || kdfname !== "none", algorithm, seed };
+}

package/src/auth/registerIdentity.ts

@@ -28,7 +28,7 @@ export function decodeJwtPayload(jwt: string): Record<string, unknown> {
 
 export function extractOrgIdFromJwt(jwt: string): string {
   const payload = decodeJwtPayload(jwt);
-  const orgId = payload["org"] ?? payload["orgId"] ?? payload["org_id"] ?? payload["organizationId"];
+  const orgId = payload.org ?? payload.orgId ?? payload.org_id ?? payload.organizationId;
   if (typeof orgId !== "string" || !orgId) {
     throw new Error("JWT does not contain an organization claim (expected org, orgId, org_id, or organizationId)");
   }

package/src/commands/misc.ts

@@ -7,6 +7,7 @@ import { generate, buildWaves, normalizeInputPattern, GenerateOptions } from "..
 import { init } from "../config";
 import { login } from "../login";
 import { registerIdentity } from "../auth/registerIdentity";
+import { ensureIdentityKeyPair } from "../auth/keyManager";
 import { KnowhowSimpleClient } from "../services/KnowhowClient";
 import { startChat } from "../chat";
 
@@ -26,21 +27,43 @@ export function addLoginCommand(program: Command): void {
     .option("--jwt", "Use manual JWT input instead of browser login")
     .option("-i, --identity <path>", "Ed25519 private key to use for public-key login")
     .option("--register-identity", "Register an Ed25519 identity using the JWT in .knowhow/.jwt")
+    .option("--key-gen", "Generate or validate the CLI Ed25519 identity keypair and exit")
     .option("--api-url <url>", "API base URL override (falls back to KNOWHOW_API_URL env)")
     .action(async (options: {
       jwt?: boolean;
       identity?: string;
       registerIdentity?: boolean;
+      keyGen?: boolean;
       apiUrl?: string;
     }) => {
+      if (options.keyGen) {
+        if (options.jwt || options.registerIdentity) {
+          throw new Error("--key-gen cannot be used with --jwt or --register-identity");
+        }
+
+        const { keyPair, created } = ensureIdentityKeyPair(options.identity);
+        if (created) {
+          console.log(`✅ Generated CLI identity keypair: ${keyPair.fingerprint}`);
+          console.log(`Private key: ${keyPair.privateKeyPath}`);
+          console.log(`Public key: ${keyPair.publicKeyPath}`);
+        } else {
+          console.log(`✅ CLI identity keypair already exists: ${keyPair.fingerprint}`);
+          console.log(`Private key: ${keyPair.privateKeyPath}`);
+          console.log(`Public key: ${keyPair.publicKeyPath}`);
+        }
+
+        return;
+      }
+
       if (options.registerIdentity) {
         await registerIdentity({
           identityPath: options.identity,
           apiUrl: options.apiUrl,
         });
-      } else {
-        await login(options.jwt, options.identity);
+        return;
       }
+
+      await login(options.jwt, options.identity);
     });
 }
 

package/tests/unit/auth/keyManager.test.ts

@@ -3,11 +3,34 @@ import fs from "fs";
 import os from "os";
 import path from "path";
 import {
+  ensureIdentityKeyPair,
   generateKeyPair,
   loadKeyPair,
   signMessage,
 } from "../../../src/auth/keyManager";
 
+const OPENSSH_ED25519_PRIVATE_KEY = `-----BEGIN OPENSSH PRIVATE KEY-----
+b3BlbnNzaC1rZXktdjEAAAAABG5vbmUAAAAEbm9uZQAAAAAAAAABAAAAMwAAAAtzc2gtZW
+QyNTUxOQAAACD/E7YSDZcV7usL3Ej3SSvGNVuNMu1hYFOpHjQaCodvIgAAAIgKqccyCqnH
+MgAAAAtzc2gtZWQyNTUxOQAAACD/E7YSDZcV7usL3Ej3SSvGNVuNMu1hYFOpHjQaCodvIg
+AAAECC40JKj3sb9Q3KsA9wAKeLbUwazUi7cuBiDfuJHDybtf8TthINlxXu6wvcSPdJK8Y1
+W40y7WFgU6keNBoKh28iAAAABHRlc3QB
+-----END OPENSSH PRIVATE KEY-----
+`;
+
+const OPENSSH_ED25519_PUBLIC_KEY =
+  "ssh-ed25519 AAAAC3NzaC1lZDI1NTE5AAAAIP8TthINlxXu6wvcSPdJK8Y1W40y7WFgU6keNBoKh28i test\n";
+
+const OPENSSH_ENCRYPTED_ED25519_PRIVATE_KEY = `-----BEGIN OPENSSH PRIVATE KEY-----
+b3BlbnNzaC1rZXktdjEAAAAACmFlczI1Ni1jdHIAAAAGYmNyeXB0AAAAGAAAABAiFkZE2t
+9UBWLQLB8sAuG7AAAAGAAAAAEAAAAzAAAAC3NzaC1lZDI1NTE5AAAAID2OnkCi/hq0EH9E
+yBf1n4FXRDw16RYyDAL0pbbRWh1JAAAAkHNPoqbcZcef7FZY+dFTRTODyAMPL4gyzOxGLE
+JffXux9KUTPBrCy+xfScoAHq9JFKrspli5h5Z6PyJ7Dp2NNJPOzEaF92fv6989AETm3X3X
+2pOUvtPMJz29C1MO7hXHlReIWqF6nkaDGGcNEZMZ3xHI4ypB/lfceH6A1IjxZEa2BXJfJe
+y6h8co4T89tJdubQ==
+-----END OPENSSH PRIVATE KEY-----
+`;
+
 describe("keyManager", () => {
   let directory: string;
   let identity: string;
@@ -42,6 +65,27 @@ describe("keyManager", () => {
     ).toBe(true);
   });
 
+  it("accepts default unencrypted OpenSSH Ed25519 private keys", () => {
+    fs.writeFileSync(identity, OPENSSH_ED25519_PRIVATE_KEY);
+    fs.writeFileSync(`${identity}.pub`, OPENSSH_ED25519_PUBLIC_KEY);
+
+    const loaded = loadKeyPair(identity);
+    expect(loaded.publicKeyBase64).toBe("/xO2Eg2XFe7rC9xI90krxjVbjTLtYWB TqR40GgqHbyI=".replace(/\s+/g, ""));
+
+    const signature = signMessage("challenge", identity);
+    const spkiPrefix = Buffer.from("302a300506032b6570032100", "hex");
+    const publicKeyDer = Buffer.concat([spkiPrefix, Buffer.from(loaded.publicKeyBase64, "base64")]);
+    const publicKey = crypto.createPublicKey({ key: publicKeyDer, format: "der", type: "spki" });
+    expect(
+      crypto.verify(
+        null,
+        Buffer.from("challenge"),
+        publicKey,
+        Buffer.from(signature, "base64")
+      )
+    ).toBe(true);
+  });
+
   it("loads legacy raw-base64 public keys but rejects non-Ed25519 identities", () => {
     const generated = generateKeyPair(identity);
     fs.writeFileSync(`${identity}.pub`, generated.publicKeyBase64);
@@ -59,9 +103,28 @@ describe("keyManager", () => {
     expect(() => loadKeyPair(rsaIdentity)).toThrow("must be an Ed25519 private key");
   });
 
+  it("rejects encrypted OpenSSH keys with a clear error", () => {
+    fs.writeFileSync(identity, OPENSSH_ENCRYPTED_ED25519_PRIVATE_KEY);
+    fs.writeFileSync(`${identity}.pub`, OPENSSH_ED25519_PUBLIC_KEY);
+
+    expect(() => loadKeyPair(identity)).toThrow("encrypted OpenSSH key");
+  });
+
   it("does not overwrite a partial identity", () => {
     fs.writeFileSync(identity, "existing key");
     expect(() => generateKeyPair(identity)).toThrow("a key file already exists");
     expect(fs.readFileSync(identity, "utf8")).toBe("existing key");
   });
+
+  it("ensureIdentityKeyPair is safe for existing keys (no overwrite)", () => {
+    const generated = generateKeyPair(identity);
+    const beforePrivate = fs.readFileSync(identity, "utf8");
+    const beforePublic = fs.readFileSync(`${identity}.pub`, "utf8");
+
+    const result = ensureIdentityKeyPair(identity);
+    expect(result.created).toBe(false);
+    expect(result.keyPair).toEqual(generated);
+    expect(fs.readFileSync(identity, "utf8")).toBe(beforePrivate);
+    expect(fs.readFileSync(`${identity}.pub`, "utf8")).toBe(beforePublic);
+  });
 });

package/tests/unit/commands/misc.test.ts

@@ -0,0 +1,85 @@
+import { Command } from "commander";
+
+const login = jest.fn().mockResolvedValue(undefined);
+const registerIdentity = jest.fn().mockResolvedValue(undefined);
+const ensureIdentityKeyPair = jest.fn();
+
+jest.mock("../../../src/login", () => ({ login }));
+jest.mock("../../../src/index", () => ({
+  embed: jest.fn(),
+  upload: jest.fn(),
+  download: jest.fn(),
+  purge: jest.fn(),
+}));
+jest.mock("../../../src/auth/registerIdentity", () => ({ registerIdentity }));
+jest.mock("../../../src/auth/keyManager", () => ({ ensureIdentityKeyPair }));
+
+import { addLoginCommand } from "../../../src/commands/misc";
+
+describe("login command", () => {
+  let program: Command;
+  let logSpy: jest.SpyInstance;
+
+  beforeEach(() => {
+    jest.clearAllMocks();
+    program = new Command();
+    program.exitOverride();
+    addLoginCommand(program);
+    logSpy = jest.spyOn(console, "log").mockImplementation(() => undefined);
+  });
+
+  afterEach(() => {
+    logSpy.mockRestore();
+  });
+
+  it("supports --key-gen non-interactively and exits without login", async () => {
+    ensureIdentityKeyPair.mockReturnValue({
+      created: true,
+      keyPair: {
+        fingerprint: "SHA256:test",
+        privateKeyPath: "/keys/id_ed25519",
+        publicKeyPath: "/keys/id_ed25519.pub",
+      },
+    });
+
+    await program.parseAsync(["node", "knowhow", "login", "--key-gen"]);
+
+    expect(ensureIdentityKeyPair).toHaveBeenCalledWith(undefined);
+    expect(login).not.toHaveBeenCalled();
+    expect(registerIdentity).not.toHaveBeenCalled();
+
+    const output = logSpy.mock.calls.map((call) => call.join(" ")).join("\n");
+    expect(output).toContain("Generated CLI identity keypair");
+    expect(output).toContain("/keys/id_ed25519");
+    expect(output).toContain("/keys/id_ed25519.pub");
+  });
+
+  it("does not overwrite existing key when using --key-gen", async () => {
+    ensureIdentityKeyPair.mockReturnValue({
+      created: false,
+      keyPair: {
+        fingerprint: "SHA256:existing",
+        privateKeyPath: "/keys/id_ed25519",
+        publicKeyPath: "/keys/id_ed25519.pub",
+      },
+    });
+
+    await program.parseAsync(["node", "knowhow", "login", "--key-gen", "--identity", "/keys/id_ed25519"]);
+
+    expect(ensureIdentityKeyPair).toHaveBeenCalledWith("/keys/id_ed25519");
+    expect(login).not.toHaveBeenCalled();
+    expect(registerIdentity).not.toHaveBeenCalled();
+
+    const output = logSpy.mock.calls.map((call) => call.join(" ")).join("\n");
+    expect(output).toContain("CLI identity keypair already exists");
+  });
+
+  it("rejects incompatible flag combinations with --key-gen", async () => {
+    await expect(
+      program.parseAsync(["node", "knowhow", "login", "--key-gen", "--jwt"])
+    ).rejects.toThrow("--key-gen cannot be used with --jwt or --register-identity");
+
+    expect(login).not.toHaveBeenCalled();
+    expect(registerIdentity).not.toHaveBeenCalled();
+  });
+});

package/ts_build/package.json

@@ -1,6 +1,6 @@
 {
     "name": "@tyvm/knowhow",
-    "version": "0.0.151",
+    "version": "0.0.153",
     "description": "ai cli with plugins and agents",
     "main": "ts_build/src/index.js",
     "bin": {

package/ts_build/src/auth/keyManager.d.ts

@@ -11,4 +11,8 @@ export declare function keyPairExists(privateKeyPath?: string): boolean;
 export declare function generateKeyPair(privateKeyPath?: string): KeyPair;
 export declare function loadKeyPair(privateKeyPath?: string): KeyPair;
 export declare function getOrCreatePublicKey(privateKeyPath?: string): KeyPair;
+export declare function ensureIdentityKeyPair(privateKeyPath?: string): {
+    keyPair: KeyPair;
+    created: boolean;
+};
 export declare function signMessage(message: string, privateKeyPath?: string): string;

package/ts_build/src/auth/keyManager.js

@@ -10,6 +10,7 @@ exports.keyPairExists = keyPairExists;
 exports.generateKeyPair = generateKeyPair;
 exports.loadKeyPair = loadKeyPair;
 exports.getOrCreatePublicKey = getOrCreatePublicKey;
+exports.ensureIdentityKeyPair = ensureIdentityKeyPair;
 exports.signMessage = signMessage;
 const crypto_1 = __importDefault(require("crypto"));
 const fs_1 = __importDefault(require("fs"));
@@ -18,6 +19,7 @@ const path_1 = __importDefault(require("path"));
 const ED25519_KEY_TYPE = "ssh-ed25519";
 const ED25519_RAW_KEY_LENGTH = 32;
 const ED25519_SPKI_PREFIX = Buffer.from("302a300506032b6570032100", "hex");
+const ED25519_PKCS8_PREFIX = Buffer.from("302e020100300506032b657004220420", "hex");
 function getKeyDir() {
     return path_1.default.join(os_1.default.homedir(), ".knowhow", "keys");
 }
@@ -76,6 +78,11 @@ function getOrCreatePublicKey(privateKeyPath) {
         ? loadKeyPair(privateKeyPath)
         : generateKeyPair(privateKeyPath);
 }
+function ensureIdentityKeyPair(privateKeyPath) {
+    if (keyPairExists(privateKeyPath))
+        return { keyPair: loadKeyPair(privateKeyPath), created: false };
+    return { keyPair: generateKeyPair(privateKeyPath), created: true };
+}
 function signMessage(message, privateKeyPath) {
     const privatePath = privateKeyPath ?? getDefaultPrivateKeyPath();
     if (!fs_1.default.existsSync(privatePath))
@@ -84,14 +91,35 @@ function signMessage(message, privateKeyPath) {
 }
 function readEd25519PrivateKey(privatePath) {
     let key;
+    const privateKeyContents = fs_1.default.readFileSync(privatePath, "utf8");
+    const openSshMetadata = parseOpenSshMetadata(privateKeyContents);
+    if (openSshMetadata?.encrypted) {
+        throw new Error(`Identity at ${privatePath} is an encrypted OpenSSH key. Use an unencrypted Ed25519 key for CLI auth (example: ssh-keygen -t ed25519 -N '' -f ${privatePath})`);
+    }
     try {
-        key = crypto_1.default.createPrivateKey(fs_1.default.readFileSync(privatePath));
+        key = crypto_1.default.createPrivateKey({ key: privateKeyContents, format: "pem" });
     }
     catch {
-        throw new Error(`Identity at ${privatePath} is not a supported PEM Ed25519 private key`);
+        if (openSshMetadata) {
+            if (openSshMetadata.algorithm && openSshMetadata.algorithm !== ED25519_KEY_TYPE) {
+                throw new Error(`Identity at ${privatePath} must be an OpenSSH Ed25519 key (found ${openSshMetadata.algorithm})`);
+            }
+            if (openSshMetadata.seed) {
+                key = createEd25519PrivateKeyFromSeed(openSshMetadata.seed, privatePath);
+            }
+            else {
+                throw new Error(`Identity at ${privatePath} must be a PKCS#8 Ed25519 private key or an unencrypted OpenSSH Ed25519 private key`);
+            }
+            return key;
+        }
+        throw new Error(`Identity at ${privatePath} must be a PKCS#8 Ed25519 private key or an unencrypted OpenSSH Ed25519 private key`);
     }
+    const detectedAlgorithm = key.asymmetricKeyType === "ed25519" ? openSshMetadata?.algorithm ?? "ed25519" : key.asymmetricKeyType;
     if (key.asymmetricKeyType !== "ed25519") {
-        throw new Error(`Identity at ${privatePath} must be an Ed25519 private key`);
+        throw new Error(`Identity at ${privatePath} must be an Ed25519 private key (found ${detectedAlgorithm ?? "unknown"})`);
+    }
+    if (openSshMetadata?.algorithm && openSshMetadata.algorithm !== ED25519_KEY_TYPE) {
+        throw new Error(`Identity at ${privatePath} must be an OpenSSH Ed25519 key (found ${openSshMetadata.algorithm})`);
     }
     return key;
 }
@@ -142,4 +170,111 @@ function keyPairMetadata(privatePath, rawPublicKey) {
         fingerprint: `SHA256:${hash}`,
     };
 }
+function createEd25519PrivateKeyFromSeed(seed, privatePath) {
+    if (seed.length !== ED25519_RAW_KEY_LENGTH) {
+        throw new Error(`Identity at ${privatePath} has an invalid OpenSSH Ed25519 private key payload`);
+    }
+    try {
+        const der = Buffer.concat([ED25519_PKCS8_PREFIX, seed]);
+        return crypto_1.default.createPrivateKey({ key: der, format: "der", type: "pkcs8" });
+    }
+    catch {
+        throw new Error(`Identity at ${privatePath} must be a PKCS#8 Ed25519 private key or an unencrypted OpenSSH Ed25519 private key`);
+    }
+}
+function parseOpenSshMetadata(privateKeyContents) {
+    const trimmed = privateKeyContents.trim();
+    if (!trimmed.startsWith("-----BEGIN OPENSSH PRIVATE KEY-----")) {
+        return undefined;
+    }
+    const body = trimmed
+        .replace("-----BEGIN OPENSSH PRIVATE KEY-----", "")
+        .replace("-----END OPENSSH PRIVATE KEY-----", "")
+        .replace(/\s+/g, "");
+    let buffer;
+    try {
+        buffer = Buffer.from(body, "base64");
+    }
+    catch {
+        return undefined;
+    }
+    let offset = 0;
+    const magic = Buffer.from("openssh-key-v1\0", "utf8");
+    if (buffer.length < magic.length || !buffer.subarray(0, magic.length).equals(magic)) {
+        return undefined;
+    }
+    offset += magic.length;
+    const readString = () => {
+        if (offset + 4 > buffer.length)
+            return undefined;
+        const length = buffer.readUInt32BE(offset);
+        offset += 4;
+        if (offset + length > buffer.length)
+            return undefined;
+        const value = buffer.subarray(offset, offset + length).toString("utf8");
+        offset += length;
+        return value;
+    };
+    const readBuffer = () => {
+        if (offset + 4 > buffer.length)
+            return undefined;
+        const length = buffer.readUInt32BE(offset);
+        offset += 4;
+        if (offset + length > buffer.length)
+            return undefined;
+        const value = buffer.subarray(offset, offset + length);
+        offset += length;
+        return value;
+    };
+    const ciphername = readString();
+    const kdfname = readString();
+    const kdfoptions = readBuffer();
+    if (!ciphername || !kdfname || !kdfoptions) {
+        return undefined;
+    }
+    if (offset + 4 > buffer.length)
+        return { encrypted: ciphername !== "none" || kdfname !== "none" };
+    const keyCount = buffer.readUInt32BE(offset);
+    offset += 4;
+    for (let i = 0; i < keyCount; i++) {
+        const skippedPublic = readBuffer();
+        if (!skippedPublic)
+            return { encrypted: ciphername !== "none" || kdfname !== "none" };
+    }
+    const privateBlock = readBuffer();
+    if (!privateBlock)
+        return { encrypted: ciphername !== "none" || kdfname !== "none" };
+    let privateOffset = 0;
+    const readPrivateString = () => {
+        if (privateOffset + 4 > privateBlock.length)
+            return undefined;
+        const length = privateBlock.readUInt32BE(privateOffset);
+        privateOffset += 4;
+        if (privateOffset + length > privateBlock.length)
+            return undefined;
+        const value = privateBlock.subarray(privateOffset, privateOffset + length).toString("utf8");
+        privateOffset += length;
+        return value;
+    };
+    const readPrivateBuffer = () => {
+        if (privateOffset + 4 > privateBlock.length)
+            return undefined;
+        const length = privateBlock.readUInt32BE(privateOffset);
+        privateOffset += 4;
+        if (privateOffset + length > privateBlock.length)
+            return undefined;
+        const value = privateBlock.subarray(privateOffset, privateOffset + length);
+        privateOffset += length;
+        return value;
+    };
+    privateOffset += 8;
+    const algorithm = readPrivateString();
+    let seed;
+    if (algorithm === ED25519_KEY_TYPE) {
+        readPrivateBuffer();
+        const privateConcat = readPrivateBuffer();
+        seed = privateConcat?.subarray(0, ED25519_RAW_KEY_LENGTH);
+    }
+    return { encrypted: ciphername !== "none" || kdfname !== "none", algorithm, seed };
+}
 //# sourceMappingURL=keyManager.js.map

package/ts_build/src/auth/keyManager.js.map

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package/ts_build/src/auth/registerIdentity.js

@@ -29,7 +29,7 @@ function decodeJwtPayload(jwt) {
 }
 function extractOrgIdFromJwt(jwt) {
     const payload = decodeJwtPayload(jwt);
-    const orgId = payload["org"] ?? payload["orgId"] ?? payload["org_id"] ?? payload["organizationId"];
+    const orgId = payload.org ?? payload.orgId ?? payload.org_id ?? payload.organizationId;
     if (typeof orgId !== "string" || !orgId) {
         throw new Error("JWT does not contain an organization claim (expected org, orgId, org_id, or organizationId)");
     }

package/ts_build/src/auth/registerIdentity.js.map

@@ -1 +1 @@
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+{"version":3,"file":"registerIdentity.js","sourceRoot":"","sources":["../../../src/auth/registerIdentity.ts"],"names":[],"mappings":";;;;;AAcA,4CAYC;AAED,kDAOC;AAQD,4CAuBC;AAlED,4CAAoB;AACpB,gDAAwB;AACxB,6CAAoD;AACpD,uCAA8E;AAC9E,sCAAoD;AAUpD,SAAgB,gBAAgB,CAAC,GAAW;IAC1C,MAAM,KAAK,GAAG,GAAG,CAAC,KAAK,CAAC,GAAG,CAAC,CAAC;IAC7B,IAAI,KAAK,CAAC,MAAM,KAAK,CAAC;QAAE,MAAM,IAAI,KAAK,CAAC,sCAAsC,CAAC,CAAC;IAChF,MAAM,MAAM,GAAG,CAAC,KAAK,CAAC,CAAC,CAAC,IAAI,EAAE,CAAC,CAAC,OAAO,CAAC,IAAI,EAAE,GAAG,CAAC,CAAC,OAAO,CAAC,IAAI,EAAE,GAAG,CAAC,CAAC;IACtE,MAAM,MAAM,GAAG,MAAM,CAAC,MAAM,CAAC,IAAI,CAAC,IAAI,CAAC,MAAM,CAAC,MAAM,GAAG,CAAC,CAAC,GAAG,CAAC,EAAE,GAAG,CAAC,CAAC;IACpE,IAAI,CAAC;QACH,MAAM,OAAO,GAAY,IAAI,CAAC,KAAK,CAAC,MAAM,CAAC,IAAI,CAAC,MAAM,EAAE,QAAQ,CAAC,CAAC,QAAQ,CAAC,MAAM,CAAC,CAAC,CAAC;QACpF,IAAI,CAAC,OAAO,IAAI,OAAO,OAAO,KAAK,QAAQ,IAAI,KAAK,CAAC,OAAO,CAAC,OAAO,CAAC;YAAE,MAAM,IAAI,KAAK,EAAE,CAAC;QACzF,OAAO,OAAkC,CAAC;IAC5C,CAAC;IAAC,MAAM,CAAC;QACP,MAAM,IAAI,KAAK,CAAC,2CAA2C,CAAC,CAAC;IAC/D,CAAC;AACH,CAAC;AAED,SAAgB,mBAAmB,CAAC,GAAW;IAC7C,MAAM,OAAO,GAAG,gBAAgB,CAAC,GAAG,CAAC,CAAC;IACtC,MAAM,KAAK,GAAG,OAAO,CAAC,GAAG,IAAI,OAAO,CAAC,KAAK,IAAI,OAAO,CAAC,MAAM,IAAI,OAAO,CAAC,cAAc,CAAC;IACvF,IAAI,OAAO,KAAK,KAAK,QAAQ,IAAI,CAAC,KAAK,EAAE,CAAC;QACxC,MAAM,IAAI,KAAK,CAAC,6FAA6F,CAAC,CAAC;IACjH,CAAC;IACD,OAAO,KAAK,CAAC;AACf,CAAC;AAQM,KAAK,UAAU,gBAAgB,CAAC,UAAmC,EAAE;IAC1E,MAAM,MAAM,GAAG,OAAO,CAAC,MAAM,IAAI,OAAO,CAAC,GAAG,CAAC,eAAe,IAAI,6BAA6B,CAAC;IAC9F,MAAM,OAAO,GAAG,cAAI,CAAC,IAAI,CAAC,OAAO,CAAC,GAAG,EAAE,EAAE,UAAU,EAAE,MAAM,CAAC,CAAC;IAC7D,IAAI,CAAC,YAAE,CAAC,UAAU,CAAC,OAAO,CAAC;QAAE,MAAM,IAAI,KAAK,CAAC,uBAAuB,OAAO,EAAE,CAAC,CAAC;IAC/E,MAAM,SAAS,GAAG,YAAE,CAAC,YAAY,CAAC,OAAO,EAAE,MAAM,CAAC,CAAC,IAAI,EAAE,CAAC;IAC1D,IAAI,CAAC,SAAS;QAAE,MAAM,IAAI,KAAK,CAAC,sBAAsB,OAAO,EAAE,CAAC,CAAC;IAEjE,MAAM,KAAK,GAAG,mBAAmB,CAAC,SAAS,CAAC,CAAC;IAC7C,MAAM,OAAO,GAAG,IAAA,iCAAoB,EAAC,OAAO,CAAC,YAAY,CAAC,CAAC;IAC3D,MAAM,IAAA,2BAAiB,EAAC,SAAS,EAAE,OAAO,CAAC,eAAe,EAAE,MAAM,CAAC,CAAC;IACpE,MAAM,WAAW,GAAG,MAAM,IAAA,8BAAoB,EAAC,KAAK,EAAE,MAAM,EAAE,OAAO,CAAC,YAAY,CAAC,CAAC;IACpF,IAAA,kBAAQ,EAAC,WAAW,CAAC,CAAC;IAEtB,MAAM,MAAM,GAAG,MAAM,IAAA,kBAAS,GAAE,CAAC;IACjC,IAAI,CAAC,MAAM,CAAC,cAAc;QAAE,MAAM,CAAC,cAAc,GAAG,EAAE,CAAC;IACvD,IAAI,CAAC,MAAM,CAAC,cAAc,CAAC,IAAI,CAAC,CAAC,QAA8B,EAAE,EAAE,CAAC,QAAQ,CAAC,QAAQ,KAAK,SAAS,CAAC,EAAE,CAAC;QACrG,MAAM,CAAC,cAAc,CAAC,IAAI,CAAC,EAAE,QAAQ,EAAE,SAAS,EAAE,CAAC,CAAC;IACtD,CAAC;IACD,MAAM,CAAC,KAAK,GAAG,KAAK,CAAC;IACrB,MAAM,CAAC,eAAe,GAAG,cAAI,CAAC,OAAO,CAAC,OAAO,CAAC,YAAY,IAAI,OAAO,CAAC,cAAc,CAAC,CAAC;IACtF,MAAM,IAAA,qBAAY,EAAC,MAAM,CAAC,CAAC;IAE3B,OAAO,CAAC,GAAG,CAAC,oCAAoC,OAAO,CAAC,WAAW,UAAU,KAAK,EAAE,CAAC,CAAC;AACxF,CAAC"}

package/ts_build/src/commands/misc.js

@@ -50,6 +50,7 @@ const generate_1 = require("../generate");
 const config_1 = require("../config");
 const login_1 = require("../login");
 const registerIdentity_1 = require("../auth/registerIdentity");
+const keyManager_1 = require("../auth/keyManager");
 const KnowhowClient_1 = require("../services/KnowhowClient");
 const chat_1 = require("../chat");
 function addInitCommand(program) {
@@ -67,17 +68,34 @@ function addLoginCommand(program) {
         .option("--jwt", "Use manual JWT input instead of browser login")
         .option("-i, --identity <path>", "Ed25519 private key to use for public-key login")
         .option("--register-identity", "Register an Ed25519 identity using the JWT in .knowhow/.jwt")
+        .option("--key-gen", "Generate or validate the CLI Ed25519 identity keypair and exit")
         .option("--api-url <url>", "API base URL override (falls back to KNOWHOW_API_URL env)")
         .action(async (options) => {
+        if (options.keyGen) {
+            if (options.jwt || options.registerIdentity) {
+                throw new Error("--key-gen cannot be used with --jwt or --register-identity");
+            }
+            const { keyPair, created } = (0, keyManager_1.ensureIdentityKeyPair)(options.identity);
+            if (created) {
+                console.log(`✅ Generated CLI identity keypair: ${keyPair.fingerprint}`);
+                console.log(`Private key: ${keyPair.privateKeyPath}`);
+                console.log(`Public key: ${keyPair.publicKeyPath}`);
+            }
+            else {
+                console.log(`✅ CLI identity keypair already exists: ${keyPair.fingerprint}`);
+                console.log(`Private key: ${keyPair.privateKeyPath}`);
+                console.log(`Public key: ${keyPair.publicKeyPath}`);
+            }
+            return;
+        }
         if (options.registerIdentity) {
             await (0, registerIdentity_1.registerIdentity)({
                 identityPath: options.identity,
                 apiUrl: options.apiUrl,
             });
+            return;
         }
-        else {
-            await (0, login_1.login)(options.jwt, options.identity);
-        }
+        await (0, login_1.login)(options.jwt, options.identity);
     });
 }
 function addUpdateCommand(program) {

package/ts_build/src/commands/misc.js.map

@@ -1 +1 @@
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package/ts_build/tests/unit/auth/keyManager.test.js

@@ -8,6 +8,24 @@ const fs_1 = __importDefault(require("fs"));
 const os_1 = __importDefault(require("os"));
 const path_1 = __importDefault(require("path"));
 const keyManager_1 = require("../../../src/auth/keyManager");
+const OPENSSH_ED25519_PRIVATE_KEY = `-----BEGIN OPENSSH PRIVATE KEY-----
+b3BlbnNzaC1rZXktdjEAAAAABG5vbmUAAAAEbm9uZQAAAAAAAAABAAAAMwAAAAtzc2gtZW
+QyNTUxOQAAACD/E7YSDZcV7usL3Ej3SSvGNVuNMu1hYFOpHjQaCodvIgAAAIgKqccyCqnH
+MgAAAAtzc2gtZWQyNTUxOQAAACD/E7YSDZcV7usL3Ej3SSvGNVuNMu1hYFOpHjQaCodvIg
+AAAECC40JKj3sb9Q3KsA9wAKeLbUwazUi7cuBiDfuJHDybtf8TthINlxXu6wvcSPdJK8Y1
+W40y7WFgU6keNBoKh28iAAAABHRlc3QB
+-----END OPENSSH PRIVATE KEY-----
+`;
+const OPENSSH_ED25519_PUBLIC_KEY = "ssh-ed25519 AAAAC3NzaC1lZDI1NTE5AAAAIP8TthINlxXu6wvcSPdJK8Y1W40y7WFgU6keNBoKh28i test\n";
+const OPENSSH_ENCRYPTED_ED25519_PRIVATE_KEY = `-----BEGIN OPENSSH PRIVATE KEY-----
+b3BlbnNzaC1rZXktdjEAAAAACmFlczI1Ni1jdHIAAAAGYmNyeXB0AAAAGAAAABAiFkZE2t
+9UBWLQLB8sAuG7AAAAGAAAAAEAAAAzAAAAC3NzaC1lZDI1NTE5AAAAID2OnkCi/hq0EH9E
+yBf1n4FXRDw16RYyDAL0pbbRWh1JAAAAkHNPoqbcZcef7FZY+dFTRTODyAMPL4gyzOxGLE
+JffXux9KUTPBrCy+xfScoAHq9JFKrspli5h5Z6PyJ7Dp2NNJPOzEaF92fv6989AETm3X3X
+2pOUvtPMJz29C1MO7hXHlReIWqF6nkaDGGcNEZMZ3xHI4ypB/lfceH6A1IjxZEa2BXJfJe
+y6h8co4T89tJdubQ==
+-----END OPENSSH PRIVATE KEY-----
+`;
 describe("keyManager", () => {
     let directory;
     let identity;
@@ -29,6 +47,17 @@ describe("keyManager", () => {
         const publicKey = crypto_1.default.createPublicKey(fs_1.default.readFileSync(identity));
         expect(crypto_1.default.verify(null, Buffer.from(challengeMessage), publicKey, Buffer.from(signature, "base64"))).toBe(true);
     });
+    it("accepts default unencrypted OpenSSH Ed25519 private keys", () => {
+        fs_1.default.writeFileSync(identity, OPENSSH_ED25519_PRIVATE_KEY);
+        fs_1.default.writeFileSync(`${identity}.pub`, OPENSSH_ED25519_PUBLIC_KEY);
+        const loaded = (0, keyManager_1.loadKeyPair)(identity);
+        expect(loaded.publicKeyBase64).toBe("/xO2Eg2XFe7rC9xI90krxjVbjTLtYWB TqR40GgqHbyI=".replace(/\s+/g, ""));
+        const signature = (0, keyManager_1.signMessage)("challenge", identity);
+        const spkiPrefix = Buffer.from("302a300506032b6570032100", "hex");
+        const publicKeyDer = Buffer.concat([spkiPrefix, Buffer.from(loaded.publicKeyBase64, "base64")]);
+        const publicKey = crypto_1.default.createPublicKey({ key: publicKeyDer, format: "der", type: "spki" });
+        expect(crypto_1.default.verify(null, Buffer.from("challenge"), publicKey, Buffer.from(signature, "base64"))).toBe(true);
+    });
     it("loads legacy raw-base64 public keys but rejects non-Ed25519 identities", () => {
         const generated = (0, keyManager_1.generateKeyPair)(identity);
         fs_1.default.writeFileSync(`${identity}.pub`, generated.publicKeyBase64);
@@ -43,10 +72,25 @@ describe("keyManager", () => {
         fs_1.default.writeFileSync(`${rsaIdentity}.pub`, generated.publicKeyBase64);
         expect(() => (0, keyManager_1.loadKeyPair)(rsaIdentity)).toThrow("must be an Ed25519 private key");
     });
+    it("rejects encrypted OpenSSH keys with a clear error", () => {
+        fs_1.default.writeFileSync(identity, OPENSSH_ENCRYPTED_ED25519_PRIVATE_KEY);
+        fs_1.default.writeFileSync(`${identity}.pub`, OPENSSH_ED25519_PUBLIC_KEY);
+        expect(() => (0, keyManager_1.loadKeyPair)(identity)).toThrow("encrypted OpenSSH key");
+    });
     it("does not overwrite a partial identity", () => {
         fs_1.default.writeFileSync(identity, "existing key");
         expect(() => (0, keyManager_1.generateKeyPair)(identity)).toThrow("a key file already exists");
         expect(fs_1.default.readFileSync(identity, "utf8")).toBe("existing key");
     });
+    it("ensureIdentityKeyPair is safe for existing keys (no overwrite)", () => {
+        const generated = (0, keyManager_1.generateKeyPair)(identity);
+        const beforePrivate = fs_1.default.readFileSync(identity, "utf8");
+        const beforePublic = fs_1.default.readFileSync(`${identity}.pub`, "utf8");
+        const result = (0, keyManager_1.ensureIdentityKeyPair)(identity);
+        expect(result.created).toBe(false);
+        expect(result.keyPair).toEqual(generated);
+        expect(fs_1.default.readFileSync(identity, "utf8")).toBe(beforePrivate);
+        expect(fs_1.default.readFileSync(`${identity}.pub`, "utf8")).toBe(beforePublic);
+    });
 });
 //# sourceMappingURL=keyManager.test.js.map

package/ts_build/tests/unit/auth/keyManager.test.js.map

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package/ts_build/tests/unit/commands/misc.test.d.ts

@@ -0,0 +1 @@
+export {};

package/ts_build/tests/unit/commands/misc.test.js

@@ -0,0 +1,70 @@
+"use strict";
+Object.defineProperty(exports, "__esModule", { value: true });
+const commander_1 = require("commander");
+const login = jest.fn().mockResolvedValue(undefined);
+const registerIdentity = jest.fn().mockResolvedValue(undefined);
+const ensureIdentityKeyPair = jest.fn();
+jest.mock("../../../src/login", () => ({ login }));
+jest.mock("../../../src/index", () => ({
+    embed: jest.fn(),
+    upload: jest.fn(),
+    download: jest.fn(),
+    purge: jest.fn(),
+}));
+jest.mock("../../../src/auth/registerIdentity", () => ({ registerIdentity }));
+jest.mock("../../../src/auth/keyManager", () => ({ ensureIdentityKeyPair }));
+const misc_1 = require("../../../src/commands/misc");
+describe("login command", () => {
+    let program;
+    let logSpy;
+    beforeEach(() => {
+        jest.clearAllMocks();
+        program = new commander_1.Command();
+        program.exitOverride();
+        (0, misc_1.addLoginCommand)(program);
+        logSpy = jest.spyOn(console, "log").mockImplementation(() => undefined);
+    });
+    afterEach(() => {
+        logSpy.mockRestore();
+    });
+    it("supports --key-gen non-interactively and exits without login", async () => {
+        ensureIdentityKeyPair.mockReturnValue({
+            created: true,
+            keyPair: {
+                fingerprint: "SHA256:test",
+                privateKeyPath: "/keys/id_ed25519",
+                publicKeyPath: "/keys/id_ed25519.pub",
+            },
+        });
+        await program.parseAsync(["node", "knowhow", "login", "--key-gen"]);
+        expect(ensureIdentityKeyPair).toHaveBeenCalledWith(undefined);
+        expect(login).not.toHaveBeenCalled();
+        expect(registerIdentity).not.toHaveBeenCalled();
+        const output = logSpy.mock.calls.map((call) => call.join(" ")).join("\n");
+        expect(output).toContain("Generated CLI identity keypair");
+        expect(output).toContain("/keys/id_ed25519");
+        expect(output).toContain("/keys/id_ed25519.pub");
+    });
+    it("does not overwrite existing key when using --key-gen", async () => {
+        ensureIdentityKeyPair.mockReturnValue({
+            created: false,
+            keyPair: {
+                fingerprint: "SHA256:existing",
+                privateKeyPath: "/keys/id_ed25519",
+                publicKeyPath: "/keys/id_ed25519.pub",
+            },
+        });
+        await program.parseAsync(["node", "knowhow", "login", "--key-gen", "--identity", "/keys/id_ed25519"]);
+        expect(ensureIdentityKeyPair).toHaveBeenCalledWith("/keys/id_ed25519");
+        expect(login).not.toHaveBeenCalled();
+        expect(registerIdentity).not.toHaveBeenCalled();
+        const output = logSpy.mock.calls.map((call) => call.join(" ")).join("\n");
+        expect(output).toContain("CLI identity keypair already exists");
+    });
+    it("rejects incompatible flag combinations with --key-gen", async () => {
+        await expect(program.parseAsync(["node", "knowhow", "login", "--key-gen", "--jwt"])).rejects.toThrow("--key-gen cannot be used with --jwt or --register-identity");
+        expect(login).not.toHaveBeenCalled();
+        expect(registerIdentity).not.toHaveBeenCalled();
+    });
+});
+//# sourceMappingURL=misc.test.js.map

package/ts_build/tests/unit/commands/misc.test.js.map

@@ -0,0 +1 @@
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