diff --git a/changelog.md b/changelog.md
index 9e3aa5e..a39b30e 100644
--- a/changelog.md
+++ b/changelog.md
@@ -1,5 +1,17 @@
 # Changelog
 
+## 2025-11-25 - 1.9.0 - feat(auth)
+Implement HMAC-SHA256 OCI JWTs; enhance PyPI & RubyGems uploads and normalize responses
+
+- AuthManager: create and validate OCI JWTs signed with HMAC-SHA256 (header.payload.signature). Signature verification, exp/nbf checks and payload decoding implemented.
+- PyPI: improved Simple API handling (PEP-691 JSON responses returned as objects), Simple HTML responses updated, upload handling enhanced to support nested/flat multipart fields, verify hashes (sha256/md5/blake2b), store files and return 201 on success.
+- RubyGems: upload flow now attempts to extract gem metadata from the .gem binary when name/version are not provided, improved validation, and upload returns 201. Added extractGemMetadata helper.
+- OCI: centralized 401 response creation (including proper WWW-Authenticate header) and HEAD behavior fixed to return no body per HTTP spec.
+- SmartRegistry: use nullish coalescing for protocol basePath defaults to avoid falsy-value bugs when basePath is an empty string.
+- Tests and helpers: test expectations adjusted (Content-Type startsWith check for HTML, PEP-691 projects is an array), test helper switched to smartarchive for packaging.
+- Package.json: added devDependency @push.rocks/smartarchive and updated dev deps.
+- Various response normalization: avoid unnecessary Buffer.from() for already-serialized objects/strings and standardize status codes for create/upload endpoints (201).
+
 ## 2025-11-24 - 1.8.0 - feat(smarts3)
 Add local smarts3 testing support and documentation
 
diff --git a/package.json b/package.json
index 9508018..3c43382 100644
--- a/package.json
+++ b/package.json
@@ -18,6 +18,7 @@
     "@git.zone/tsbundle": "^2.0.5",
     "@git.zone/tsrun": "^2.0.0",
     "@git.zone/tstest": "^3.1.0",
+    "@push.rocks/smartarchive": "^5.0.1",
     "@push.rocks/smarts3": "^5.1.0",
     "@types/node": "^24.10.1"
   },
diff --git a/pnpm-lock.yaml b/pnpm-lock.yaml
index f3e9408..c9e0aac 100644
--- a/pnpm-lock.yaml
+++ b/pnpm-lock.yaml
@@ -39,6 +39,9 @@ importers:
       '@git.zone/tstest':
         specifier: ^3.1.0
         version: 3.1.0(socks@2.8.7)(typescript@5.9.3)
+      '@push.rocks/smartarchive':
+        specifier: ^5.0.1
+        version: 5.0.1(@push.rocks/smartfs@1.1.0)
       '@push.rocks/smarts3':
         specifier: ^5.1.0
         version: 5.1.0
@@ -705,6 +708,9 @@ packages:
   '@push.rocks/smartarchive@4.2.2':
     resolution: {integrity: sha512-6EpqbKU32D6Gcqsc9+Tn1dOCU5HoTlrqqs/7IdUr9Tirp9Ngtptkapca1Fw/D0kVJ7SSw3kG/miAYnuPMZLEoA==}
 
+  '@push.rocks/smartarchive@5.0.1':
+    resolution: {integrity: sha512-x4bie9IIdL9BZqBZLc8Pemp8xZOJGa6mXSVgKJRL4/Rw+E5N4rVHjQOYGRV75nC2mAMJh9GIbixuxLnWjj77ag==}
+
   '@push.rocks/smartbrowser@2.0.8':
     resolution: {integrity: sha512-0KWRZj3TuKo/sNwgPbiSE6WL+TMeR19t1JmXBZWh9n8iA2mpc4HhMrQAndEUdRCkx5ofSaHWojIRVFzGChj0Dg==}
 
@@ -765,6 +771,14 @@ packages:
   '@push.rocks/smartfile@11.2.7':
     resolution: {integrity: sha512-8Yp7/sAgPpWJBHohV92ogHWKzRomI5MEbSG6b5W2n18tqwfAmjMed0rQvsvGrSBlnEWCKgoOrYIIZbLO61+J0Q==}
 
+  '@push.rocks/smartfile@13.0.1':
+    resolution: {integrity: sha512-phtryDFtBYHo7R2H9V3Y7VeiYQU9YzKL140gKD3bTicBgXoIYrJ6+b3mbZunSO2yQt1Vy1AxCxYXrFE/K+4grw==}
+    peerDependencies:
+      '@push.rocks/smartfs': ^1.0.0
+    peerDependenciesMeta:
+      '@push.rocks/smartfs':
+        optional: true
+
   '@push.rocks/smartfs@1.1.0':
     resolution: {integrity: sha512-fg8JIjFUPPX5laRoBpTaGwhMfZ3Y8mFT4fUaW54Y4J/BfOBa/y0+rIFgvgvqcOZgkQlyZU+FIfL8Z6zezqxyTg==}
 
@@ -5265,6 +5279,27 @@ snapshots:
       - react-native-b4a
       - supports-color
 
+  '@push.rocks/smartarchive@5.0.1(@push.rocks/smartfs@1.1.0)':
+    dependencies:
+      '@push.rocks/smartdelay': 3.0.5
+      '@push.rocks/smartfile': 13.0.1(@push.rocks/smartfs@1.1.0)
+      '@push.rocks/smartpath': 6.0.0
+      '@push.rocks/smartpromise': 4.2.3
+      '@push.rocks/smartrequest': 4.4.2
+      '@push.rocks/smartrx': 3.0.10
+      '@push.rocks/smartstream': 3.2.5
+      '@push.rocks/smartunique': 3.0.9
+      '@push.rocks/smarturl': 3.1.0
+      '@types/tar-stream': 3.1.4
+      fflate: 0.8.2
+      file-type: 21.1.0
+      tar-stream: 3.1.7
+    transitivePeerDependencies:
+      - '@push.rocks/smartfs'
+      - bare-abort-controller
+      - react-native-b4a
+      - supports-color
+
   '@push.rocks/smartbrowser@2.0.8(typescript@5.9.3)':
     dependencies:
       '@push.rocks/smartdelay': 3.0.5
@@ -5453,6 +5488,24 @@ snapshots:
       glob: 11.1.0
       js-yaml: 4.1.1
 
+  '@push.rocks/smartfile@13.0.1(@push.rocks/smartfs@1.1.0)':
+    dependencies:
+      '@push.rocks/lik': 6.2.2
+      '@push.rocks/smartdelay': 3.0.5
+      '@push.rocks/smartfile-interfaces': 1.0.7
+      '@push.rocks/smarthash': 3.2.6
+      '@push.rocks/smartjson': 5.2.0
+      '@push.rocks/smartmime': 2.0.4
+      '@push.rocks/smartpath': 6.0.0
+      '@push.rocks/smartpromise': 4.2.3
+      '@push.rocks/smartrequest': 4.4.2
+      '@push.rocks/smartstream': 3.2.5
+      '@types/js-yaml': 4.0.9
+      glob: 11.1.0
+      js-yaml: 4.1.1
+    optionalDependencies:
+      '@push.rocks/smartfs': 1.1.0
+
   '@push.rocks/smartfs@1.1.0':
     dependencies:
       '@push.rocks/smartpath': 6.0.0
diff --git a/test/helpers/registry.ts b/test/helpers/registry.ts
index 0137219..4830ab4 100644
--- a/test/helpers/registry.ts
+++ b/test/helpers/registry.ts
@@ -1,5 +1,6 @@
 import * as qenv from '@push.rocks/qenv';
 import * as crypto from 'crypto';
+import * as smartarchive from '@push.rocks/smartarchive';
 import { SmartRegistry } from '../../ts/classes.smartregistry.js';
 import type { IRegistryConfig } from '../../ts/core/interfaces.core.js';
 
@@ -241,7 +242,7 @@ export function calculateMavenChecksums(data: Buffer) {
 }
 
 /**
- * Helper to create a Composer package ZIP
+ * Helper to create a Composer package ZIP using smartarchive
  */
 export async function createComposerZip(
   vendorPackage: string,
@@ -252,8 +253,7 @@ export async function createComposerZip(
     authors?: Array<{ name: string; email?: string }>;
   }
 ): Promise<Buffer> {
-  const AdmZip = (await import('adm-zip')).default;
-  const zip = new AdmZip();
+  const zipTools = new smartarchive.ZipTools();
 
   const composerJson = {
     name: vendorPackage,
@@ -272,9 +272,6 @@ export async function createComposerZip(
     },
   };
 
-  // Add composer.json
-  zip.addFile('composer.json', Buffer.from(JSON.stringify(composerJson, null, 2), 'utf-8'));
-
   // Add a test PHP file
   const [vendor, pkg] = vendorPackage.split('/');
   const namespace = `${vendor.charAt(0).toUpperCase() + vendor.slice(1)}\\${pkg.charAt(0).toUpperCase() + pkg.slice(1).replace(/-/g, '')}`;
@@ -290,24 +287,33 @@ class TestClass
 }
 `;
 
-  zip.addFile('src/TestClass.php', Buffer.from(testPhpContent, 'utf-8'));
+  const entries: smartarchive.IArchiveEntry[] = [
+    {
+      archivePath: 'composer.json',
+      content: Buffer.from(JSON.stringify(composerJson, null, 2), 'utf-8'),
+    },
+    {
+      archivePath: 'src/TestClass.php',
+      content: Buffer.from(testPhpContent, 'utf-8'),
+    },
+    {
+      archivePath: 'README.md',
+      content: Buffer.from(`# ${vendorPackage}\n\nTest package`, 'utf-8'),
+    },
+  ];
 
-  // Add README
-  zip.addFile('README.md', Buffer.from(`# ${vendorPackage}\n\nTest package`, 'utf-8'));
-
-  return zip.toBuffer();
+  return zipTools.createZip(entries);
 }
 
 /**
- * Helper to create a test Python wheel file (minimal ZIP structure)
+ * Helper to create a test Python wheel file (minimal ZIP structure) using smartarchive
  */
 export async function createPythonWheel(
   packageName: string,
   version: string,
   pyVersion: string = 'py3'
 ): Promise<Buffer> {
-  const AdmZip = (await import('adm-zip')).default;
-  const zip = new AdmZip();
+  const zipTools = new smartarchive.ZipTools();
 
   const normalizedName = packageName.replace(/-/g, '_');
   const distInfoDir = `${normalizedName}-${version}.dist-info`;
@@ -331,8 +337,6 @@ Description-Content-Type: text/markdown
 Test package for SmartRegistry
 `;
 
-  zip.addFile(`${distInfoDir}/METADATA`, Buffer.from(metadata, 'utf-8'));
-
   // Create WHEEL file
   const wheelContent = `Wheel-Version: 1.0
 Generator: test 1.0.0
@@ -340,14 +344,6 @@ Root-Is-Purelib: true
 Tag: ${pyVersion}-none-any
 `;
 
-  zip.addFile(`${distInfoDir}/WHEEL`, Buffer.from(wheelContent, 'utf-8'));
-
-  // Create RECORD file (empty for test)
-  zip.addFile(`${distInfoDir}/RECORD`, Buffer.from('', 'utf-8'));
-
-  // Create top_level.txt
-  zip.addFile(`${distInfoDir}/top_level.txt`, Buffer.from(normalizedName, 'utf-8'));
-
   // Create a simple Python module
   const moduleContent = `"""${packageName} module"""
 
@@ -357,27 +353,44 @@ def hello():
     return "Hello from ${packageName}!"
 `;
 
-  zip.addFile(`${normalizedName}/__init__.py`, Buffer.from(moduleContent, 'utf-8'));
+  const entries: smartarchive.IArchiveEntry[] = [
+    {
+      archivePath: `${distInfoDir}/METADATA`,
+      content: Buffer.from(metadata, 'utf-8'),
+    },
+    {
+      archivePath: `${distInfoDir}/WHEEL`,
+      content: Buffer.from(wheelContent, 'utf-8'),
+    },
+    {
+      archivePath: `${distInfoDir}/RECORD`,
+      content: Buffer.from('', 'utf-8'),
+    },
+    {
+      archivePath: `${distInfoDir}/top_level.txt`,
+      content: Buffer.from(normalizedName, 'utf-8'),
+    },
+    {
+      archivePath: `${normalizedName}/__init__.py`,
+      content: Buffer.from(moduleContent, 'utf-8'),
+    },
+  ];
 
-  return zip.toBuffer();
+  return zipTools.createZip(entries);
 }
 
 /**
- * Helper to create a test Python source distribution (sdist)
+ * Helper to create a test Python source distribution (sdist) using smartarchive
  */
 export async function createPythonSdist(
   packageName: string,
   version: string
 ): Promise<Buffer> {
-  const tar = await import('tar-stream');
-  const zlib = await import('zlib');
-  const { Readable } = await import('stream');
+  const tarTools = new smartarchive.TarTools();
 
   const normalizedName = packageName.replace(/-/g, '_');
   const dirPrefix = `${packageName}-${version}`;
 
-  const pack = tar.pack();
-
   // PKG-INFO
   const pkgInfo = `Metadata-Version: 2.1
 Name: ${packageName}
@@ -389,8 +402,6 @@ Author-email: test@example.com
 License: MIT
 `;
 
-  pack.entry({ name: `${dirPrefix}/PKG-INFO` }, pkgInfo);
-
   // setup.py
   const setupPy = `from setuptools import setup, find_packages
 
@@ -402,8 +413,6 @@ setup(
 )
 `;
 
-  pack.entry({ name: `${dirPrefix}/setup.py` }, setupPy);
-
   // Module file
   const moduleContent = `"""${packageName} module"""
 
@@ -413,20 +422,22 @@ def hello():
     return "Hello from ${packageName}!"
 `;
 
-  pack.entry({ name: `${dirPrefix}/${normalizedName}/__init__.py` }, moduleContent);
+  const entries: smartarchive.IArchiveEntry[] = [
+    {
+      archivePath: `${dirPrefix}/PKG-INFO`,
+      content: Buffer.from(pkgInfo, 'utf-8'),
+    },
+    {
+      archivePath: `${dirPrefix}/setup.py`,
+      content: Buffer.from(setupPy, 'utf-8'),
+    },
+    {
+      archivePath: `${dirPrefix}/${normalizedName}/__init__.py`,
+      content: Buffer.from(moduleContent, 'utf-8'),
+    },
+  ];
 
-  pack.finalize();
-
-  // Convert to gzipped tar
-  const chunks: Buffer[] = [];
-  const gzip = zlib.createGzip();
-
-  return new Promise((resolve, reject) => {
-    pack.pipe(gzip);
-    gzip.on('data', (chunk) => chunks.push(chunk));
-    gzip.on('end', () => resolve(Buffer.concat(chunks)));
-    gzip.on('error', reject);
-  });
+  return tarTools.packFilesToTarGz(entries);
 }
 
 /**
@@ -441,17 +452,15 @@ export function calculatePypiHashes(data: Buffer) {
 }
 
 /**
- * Helper to create a test RubyGem file (minimal tar.gz structure)
+ * Helper to create a test RubyGem file (minimal tar.gz structure) using smartarchive
  */
 export async function createRubyGem(
   gemName: string,
   version: string,
   platform: string = 'ruby'
 ): Promise<Buffer> {
-  const tar = await import('tar-stream');
-  const zlib = await import('zlib');
-
-  const pack = tar.pack();
+  const tarTools = new smartarchive.TarTools();
+  const gzipTools = new smartarchive.GzipTools();
 
   // Create metadata.gz (simplified)
   const metadataYaml = `--- !ruby/object:Gem::Specification
@@ -499,10 +508,9 @@ summary: Test gem for SmartRegistry
 test_files: []
 `;
 
-  pack.entry({ name: 'metadata.gz' }, zlib.gzipSync(Buffer.from(metadataYaml, 'utf-8')));
+  const metadataGz = await gzipTools.compress(Buffer.from(metadataYaml, 'utf-8'));
 
-  // Create data.tar.gz (simplified)
-  const dataPack = tar.pack();
+  // Create data.tar.gz content
   const libContent = `# ${gemName}
 
 module ${gemName.charAt(0).toUpperCase() + gemName.slice(1).replace(/-/g, '')}
@@ -514,32 +522,28 @@ module ${gemName.charAt(0).toUpperCase() + gemName.slice(1).replace(/-/g, '')}
 end
 `;
 
-  dataPack.entry({ name: `lib/${gemName}.rb` }, libContent);
-  dataPack.finalize();
+  const dataEntries: smartarchive.IArchiveEntry[] = [
+    {
+      archivePath: `lib/${gemName}.rb`,
+      content: Buffer.from(libContent, 'utf-8'),
+    },
+  ];
 
-  const dataChunks: Buffer[] = [];
-  const dataGzip = zlib.createGzip();
-  dataPack.pipe(dataGzip);
+  const dataTarGz = await tarTools.packFilesToTarGz(dataEntries);
 
-  await new Promise((resolve) => {
-    dataGzip.on('data', (chunk) => dataChunks.push(chunk));
-    dataGzip.on('end', resolve);
-  });
+  // Create the outer gem (tar.gz containing metadata.gz and data.tar.gz)
+  const gemEntries: smartarchive.IArchiveEntry[] = [
+    {
+      archivePath: 'metadata.gz',
+      content: metadataGz,
+    },
+    {
+      archivePath: 'data.tar.gz',
+      content: dataTarGz,
+    },
+  ];
 
-  pack.entry({ name: 'data.tar.gz' }, Buffer.concat(dataChunks));
-
-  pack.finalize();
-
-  // Convert to gzipped tar
-  const chunks: Buffer[] = [];
-  const gzip = zlib.createGzip();
-
-  return new Promise((resolve, reject) => {
-    pack.pipe(gzip);
-    gzip.on('data', (chunk) => chunks.push(chunk));
-    gzip.on('end', () => resolve(Buffer.concat(chunks)));
-    gzip.on('error', reject);
-  });
+  return tarTools.packFilesToTarGz(gemEntries);
 }
 
 /**
diff --git a/test/test.integration.pypi-rubygems.ts b/test/test.integration.crossprotocol.ts
similarity index 99%
rename from test/test.integration.pypi-rubygems.ts
rename to test/test.integration.crossprotocol.ts
index 98a2865..bf53b25 100644
--- a/test/test.integration.pypi-rubygems.ts
+++ b/test/test.integration.crossprotocol.ts
@@ -78,7 +78,7 @@ tap.test('Integration: should handle /simple path for PyPI', async () => {
   });
 
   expect(response.status).toEqual(200);
-  expect(response.headers['Content-Type']).toEqual('text/html');
+  expect(response.headers['Content-Type']).toStartWith('text/html');
   expect(response.body).toContain('integration-test-py');
 });
 
diff --git a/test/test.pypi.ts b/test/test.pypi.ts
index 6e20b28..b97eee8 100644
--- a/test/test.pypi.ts
+++ b/test/test.pypi.ts
@@ -99,7 +99,7 @@ tap.test('PyPI: should retrieve Simple API root index HTML (GET /simple/)', asyn
   });
 
   expect(response.status).toEqual(200);
-  expect(response.headers['Content-Type']).toEqual('text/html');
+  expect(response.headers['Content-Type']).toStartWith('text/html');
   expect(response.body).toBeTypeOf('string');
 
   const html = response.body as string;
@@ -125,8 +125,10 @@ tap.test('PyPI: should retrieve Simple API root index JSON (GET /simple/ with Ac
   const json = response.body as any;
   expect(json).toHaveProperty('meta');
   expect(json).toHaveProperty('projects');
-  expect(json.projects).toBeTypeOf('object');
-  expect(json.projects).toHaveProperty(normalizedPackageName);
+  expect(json.projects).toBeInstanceOf(Array);
+  // Check that the package is in the projects list (PEP 691 format: array of { name } objects)
+  const packageNames = json.projects.map((p: any) => p.name);
+  expect(packageNames).toContain(normalizedPackageName);
 });
 
 tap.test('PyPI: should retrieve Simple API package HTML (GET /simple/{package}/)', async () => {
@@ -140,7 +142,7 @@ tap.test('PyPI: should retrieve Simple API package HTML (GET /simple/{package}/)
   });
 
   expect(response.status).toEqual(200);
-  expect(response.headers['Content-Type']).toEqual('text/html');
+  expect(response.headers['Content-Type']).toStartWith('text/html');
   expect(response.body).toBeTypeOf('string');
 
   const html = response.body as string;
diff --git a/test/test.rubygems.nativecli.node.ts b/test/test.rubygems.nativecli.node.ts
new file mode 100644
index 0000000..2027588
--- /dev/null
+++ b/test/test.rubygems.nativecli.node.ts
@@ -0,0 +1,448 @@
+/**
+ * Native gem CLI Testing
+ * Tests the RubyGems registry implementation using the actual gem CLI
+ */
+
+import { expect, tap } from '@git.zone/tstest/tapbundle';
+import { tapNodeTools } from '@git.zone/tstest/tapbundle_serverside';
+import { SmartRegistry } from '../ts/index.js';
+import { createTestRegistry, createTestTokens, createRubyGem } from './helpers/registry.js';
+import type { IRequestContext, IResponse } from '../ts/core/interfaces.core.js';
+import * as http from 'http';
+import * as url from 'url';
+import * as fs from 'fs';
+import * as path from 'path';
+
+// Test context
+let registry: SmartRegistry;
+let server: http.Server;
+let registryUrl: string;
+let registryPort: number;
+let rubygemsToken: string;
+let testDir: string;
+let gemHome: string;
+
+/**
+ * Create HTTP server wrapper around SmartRegistry
+ */
+async function createHttpServer(
+  registryInstance: SmartRegistry,
+  port: number
+): Promise<{ server: http.Server; url: string }> {
+  return new Promise((resolve, reject) => {
+    const httpServer = http.createServer(async (req, res) => {
+      try {
+        // Parse request
+        const parsedUrl = url.parse(req.url || '', true);
+        const pathname = parsedUrl.pathname || '/';
+        const query = parsedUrl.query;
+
+        // Read body
+        const chunks: Buffer[] = [];
+        for await (const chunk of req) {
+          chunks.push(chunk);
+        }
+        const bodyBuffer = Buffer.concat(chunks);
+
+        // Parse body based on content type
+        let body: any;
+        if (bodyBuffer.length > 0) {
+          const contentType = req.headers['content-type'] || '';
+          if (contentType.includes('application/json')) {
+            try {
+              body = JSON.parse(bodyBuffer.toString('utf-8'));
+            } catch (error) {
+              body = bodyBuffer;
+            }
+          } else {
+            body = bodyBuffer;
+          }
+        }
+
+        // Convert to IRequestContext
+        const context: IRequestContext = {
+          method: req.method || 'GET',
+          path: pathname,
+          headers: req.headers as Record<string, string>,
+          query: query as Record<string, string>,
+          body: body,
+        };
+
+        // Handle request
+        const response: IResponse = await registryInstance.handleRequest(context);
+
+        // Convert IResponse to HTTP response
+        res.statusCode = response.status;
+
+        // Set headers
+        for (const [key, value] of Object.entries(response.headers || {})) {
+          res.setHeader(key, value);
+        }
+
+        // Send body
+        if (response.body) {
+          if (Buffer.isBuffer(response.body)) {
+            res.end(response.body);
+          } else if (typeof response.body === 'string') {
+            res.end(response.body);
+          } else {
+            res.setHeader('Content-Type', 'application/json');
+            res.end(JSON.stringify(response.body));
+          }
+        } else {
+          res.end();
+        }
+      } catch (error) {
+        console.error('Server error:', error);
+        res.statusCode = 500;
+        res.setHeader('Content-Type', 'application/json');
+        res.end(JSON.stringify({ error: 'INTERNAL_ERROR', message: String(error) }));
+      }
+    });
+
+    httpServer.listen(port, () => {
+      const serverUrl = `http://localhost:${port}`;
+      resolve({ server: httpServer, url: serverUrl });
+    });
+
+    httpServer.on('error', reject);
+  });
+}
+
+/**
+ * Setup gem credentials file
+ * Format: YAML with :rubygems_api_key: TOKEN
+ */
+function setupGemCredentials(token: string, gemHomeArg: string): string {
+  const gemDir = path.join(gemHomeArg, '.gem');
+  fs.mkdirSync(gemDir, { recursive: true });
+
+  // Create credentials file in YAML format
+  const credentialsContent = `:rubygems_api_key: ${token}\n`;
+
+  const credentialsPath = path.join(gemDir, 'credentials');
+  fs.writeFileSync(credentialsPath, credentialsContent, 'utf-8');
+
+  // Set restrictive permissions (gem requires 0600)
+  fs.chmodSync(credentialsPath, 0o600);
+
+  return credentialsPath;
+}
+
+/**
+ * Create a test gem file
+ */
+async function createTestGemFile(
+  gemName: string,
+  version: string,
+  targetDir: string
+): Promise<string> {
+  const gemData = await createRubyGem(gemName, version);
+  const gemFilename = `${gemName}-${version}.gem`;
+  const gemPath = path.join(targetDir, gemFilename);
+
+  fs.writeFileSync(gemPath, gemData);
+
+  return gemPath;
+}
+
+/**
+ * Run gem command with proper environment
+ */
+async function runGemCommand(
+  command: string,
+  cwd: string,
+  includeAuth: boolean = true
+): Promise<{ stdout: string; stderr: string; exitCode: number }> {
+  // Prepare environment variables
+  const envVars = [
+    `HOME="${gemHome}"`,
+    `GEM_HOME="${gemHome}"`,
+    includeAuth ? '' : 'RUBYGEMS_API_KEY=""',
+  ].filter(Boolean).join(' ');
+
+  // Build command with cd to correct directory and environment variables
+  const fullCommand = `cd "${cwd}" && ${envVars} ${command}`;
+
+  try {
+    const result = await tapNodeTools.runCommand(fullCommand);
+    return {
+      stdout: result.stdout || '',
+      stderr: result.stderr || '',
+      exitCode: result.exitCode || 0,
+    };
+  } catch (error: any) {
+    return {
+      stdout: error.stdout || '',
+      stderr: error.stderr || String(error),
+      exitCode: error.exitCode || 1,
+    };
+  }
+}
+
+/**
+ * Cleanup test directory
+ */
+function cleanupTestDir(dir: string): void {
+  if (fs.existsSync(dir)) {
+    fs.rmSync(dir, { recursive: true, force: true });
+  }
+}
+
+// ========================================================================
+// TESTS
+// ========================================================================
+
+tap.test('RubyGems CLI: should setup registry and HTTP server', async () => {
+  // Create registry
+  registry = await createTestRegistry();
+  const tokens = await createTestTokens(registry);
+  rubygemsToken = tokens.rubygemsToken;
+
+  expect(registry).toBeInstanceOf(SmartRegistry);
+  expect(rubygemsToken).toBeTypeOf('string');
+
+  // Use port 36000 (avoids npm:35000, cargo:5000 conflicts)
+  registryPort = 36000;
+  const serverSetup = await createHttpServer(registry, registryPort);
+  server = serverSetup.server;
+  registryUrl = serverSetup.url;
+
+  expect(server).toBeDefined();
+  expect(registryUrl).toEqual(`http://localhost:${registryPort}`);
+
+  // Setup test directory
+  testDir = path.join(process.cwd(), '.nogit', 'test-rubygems-cli');
+  cleanupTestDir(testDir);
+  fs.mkdirSync(testDir, { recursive: true });
+
+  // Setup GEM_HOME
+  gemHome = path.join(testDir, '.gem-home');
+  fs.mkdirSync(gemHome, { recursive: true });
+
+  // Setup gem credentials
+  const credentialsPath = setupGemCredentials(rubygemsToken, gemHome);
+  expect(fs.existsSync(credentialsPath)).toEqual(true);
+
+  // Verify credentials file has correct permissions
+  const stats = fs.statSync(credentialsPath);
+  const mode = stats.mode & 0o777;
+  expect(mode).toEqual(0o600);
+});
+
+tap.test('RubyGems CLI: should verify server is responding', async () => {
+  // Check server is up by doing a direct HTTP request to the Compact Index
+  const response = await fetch(`${registryUrl}/rubygems/versions`);
+  expect(response.status).toBeGreaterThanOrEqual(200);
+  expect(response.status).toBeLessThan(500);
+});
+
+tap.test('RubyGems CLI: should build and push a gem', async () => {
+  const gemName = 'test-gem-cli';
+  const version = '1.0.0';
+  const gemPath = await createTestGemFile(gemName, version, testDir);
+
+  expect(fs.existsSync(gemPath)).toEqual(true);
+
+  const result = await runGemCommand(
+    `gem push ${gemPath} --host ${registryUrl}/rubygems`,
+    testDir
+  );
+  console.log('gem push output:', result.stdout);
+  console.log('gem push stderr:', result.stderr);
+
+  expect(result.exitCode).toEqual(0);
+  expect(result.stdout || result.stderr).toContain(gemName);
+});
+
+tap.test('RubyGems CLI: should verify gem in Compact Index /versions', async () => {
+  const gemName = 'test-gem-cli';
+
+  const response = await fetch(`${registryUrl}/rubygems/versions`);
+  expect(response.status).toEqual(200);
+
+  const versionsData = await response.text();
+  console.log('Versions data:', versionsData);
+
+  // Format: GEMNAME VERSION[,VERSION...] MD5
+  expect(versionsData).toContain(gemName);
+  expect(versionsData).toContain('1.0.0');
+});
+
+tap.test('RubyGems CLI: should verify gem in Compact Index /info file', async () => {
+  const gemName = 'test-gem-cli';
+
+  const response = await fetch(`${registryUrl}/rubygems/info/${gemName}`);
+  expect(response.status).toEqual(200);
+
+  const infoData = await response.text();
+  console.log('Info data:', infoData);
+
+  // Format: VERSION [DEPS]|REQS
+  expect(infoData).toContain('1.0.0');
+});
+
+tap.test('RubyGems CLI: should download gem file', async () => {
+  const gemName = 'test-gem-cli';
+  const version = '1.0.0';
+
+  const response = await fetch(`${registryUrl}/rubygems/gems/${gemName}-${version}.gem`);
+  expect(response.status).toEqual(200);
+
+  const gemData = await response.arrayBuffer();
+  expect(gemData.byteLength).toBeGreaterThan(0);
+
+  // Verify content type
+  expect(response.headers.get('content-type')).toContain('application/octet-stream');
+});
+
+tap.test('RubyGems CLI: should fetch gem metadata JSON', async () => {
+  const gemName = 'test-gem-cli';
+
+  const response = await fetch(`${registryUrl}/rubygems/api/v1/versions/${gemName}.json`);
+  expect(response.status).toEqual(200);
+
+  const metadata = await response.json();
+  console.log('Metadata:', metadata);
+
+  expect(metadata).toBeInstanceOf(Array);
+  expect(metadata.length).toBeGreaterThan(0);
+  expect(metadata[0].number).toEqual('1.0.0');
+});
+
+tap.test('RubyGems CLI: should push second version', async () => {
+  const gemName = 'test-gem-cli';
+  const version = '2.0.0';
+  const gemPath = await createTestGemFile(gemName, version, testDir);
+
+  const result = await runGemCommand(
+    `gem push ${gemPath} --host ${registryUrl}/rubygems`,
+    testDir
+  );
+  console.log('gem push v2.0.0 output:', result.stdout);
+
+  expect(result.exitCode).toEqual(0);
+});
+
+tap.test('RubyGems CLI: should list all versions in /versions file', async () => {
+  const gemName = 'test-gem-cli';
+
+  const response = await fetch(`${registryUrl}/rubygems/versions`);
+  expect(response.status).toEqual(200);
+
+  const versionsData = await response.text();
+  console.log('All versions data:', versionsData);
+
+  // Should contain both versions
+  expect(versionsData).toContain(gemName);
+  expect(versionsData).toContain('1.0.0');
+  expect(versionsData).toContain('2.0.0');
+});
+
+tap.test('RubyGems CLI: should yank a version', async () => {
+  const gemName = 'test-gem-cli';
+  const version = '1.0.0';
+
+  const result = await runGemCommand(
+    `gem yank ${gemName} -v ${version} --host ${registryUrl}/rubygems`,
+    testDir
+  );
+  console.log('gem yank output:', result.stdout);
+  console.log('gem yank stderr:', result.stderr);
+
+  expect(result.exitCode).toEqual(0);
+
+  // Verify version is yanked in /versions file
+  // Yanked versions are prefixed with '-'
+  const response = await fetch(`${registryUrl}/rubygems/versions`);
+  const versionsData = await response.text();
+  console.log('Versions after yank:', versionsData);
+
+  // Yanked version should have '-' prefix
+  expect(versionsData).toContain('-1.0.0');
+});
+
+tap.test('RubyGems CLI: should unyank a version', async () => {
+  const gemName = 'test-gem-cli';
+  const version = '1.0.0';
+
+  const result = await runGemCommand(
+    `gem yank ${gemName} -v ${version} --undo --host ${registryUrl}/rubygems`,
+    testDir
+  );
+  console.log('gem unyank output:', result.stdout);
+  console.log('gem unyank stderr:', result.stderr);
+
+  expect(result.exitCode).toEqual(0);
+
+  // Verify version is not yanked in /versions file
+  const response = await fetch(`${registryUrl}/rubygems/versions`);
+  const versionsData = await response.text();
+  console.log('Versions after unyank:', versionsData);
+
+  // Should not have '-' prefix anymore (or have both without prefix)
+  // Check that we have the version without yank marker
+  const lines = versionsData.trim().split('\n');
+  const gemLine = lines.find(line => line.startsWith(gemName));
+
+  if (gemLine) {
+    // Parse format: "gemname version[,version...] md5"
+    const parts = gemLine.split(' ');
+    const versions = parts[1];
+
+    // Should have 1.0.0 without '-' prefix
+    expect(versions).toContain('1.0.0');
+    expect(versions).not.toContain('-1.0.0');
+  }
+});
+
+tap.test('RubyGems CLI: should fetch dependencies', async () => {
+  const gemName = 'test-gem-cli';
+
+  const response = await fetch(`${registryUrl}/rubygems/api/v1/dependencies?gems=${gemName}`);
+  expect(response.status).toEqual(200);
+
+  const dependencies = await response.json();
+  console.log('Dependencies:', dependencies);
+
+  expect(dependencies).toBeInstanceOf(Array);
+});
+
+tap.test('RubyGems CLI: should fail to push without auth', async () => {
+  const gemName = 'unauth-gem';
+  const version = '1.0.0';
+  const gemPath = await createTestGemFile(gemName, version, testDir);
+
+  // Run without auth
+  const result = await runGemCommand(
+    `gem push ${gemPath} --host ${registryUrl}/rubygems`,
+    testDir,
+    false
+  );
+  console.log('gem push unauth output:', result.stdout);
+  console.log('gem push unauth stderr:', result.stderr);
+
+  // Should fail with auth error
+  expect(result.exitCode).not.toEqual(0);
+});
+
+tap.postTask('cleanup rubygems cli tests', async () => {
+  // Stop server
+  if (server) {
+    await new Promise<void>((resolve) => {
+      server.close(() => resolve());
+    });
+  }
+
+  // Cleanup test directory
+  if (testDir) {
+    cleanupTestDir(testDir);
+  }
+
+  // Destroy registry
+  if (registry) {
+    registry.destroy();
+  }
+});
+
+export default tap.start();
diff --git a/ts/00_commitinfo_data.ts b/ts/00_commitinfo_data.ts
index 4f46650..a8b01ab 100644
--- a/ts/00_commitinfo_data.ts
+++ b/ts/00_commitinfo_data.ts
@@ -3,6 +3,6 @@
  */
 export const commitinfo = {
   name: '@push.rocks/smartregistry',
-  version: '1.8.0',
+  version: '1.9.0',
   description: 'A composable TypeScript library implementing OCI, NPM, Maven, Cargo, Composer, PyPI, and RubyGems registries for building unified container and package registries'
 }
diff --git a/ts/classes.smartregistry.ts b/ts/classes.smartregistry.ts
index f55abde..81be292 100644
--- a/ts/classes.smartregistry.ts
+++ b/ts/classes.smartregistry.ts
@@ -41,7 +41,7 @@ export class SmartRegistry {
 
     // Initialize OCI registry if enabled
     if (this.config.oci?.enabled) {
-      const ociBasePath = this.config.oci.basePath || '/oci';
+      const ociBasePath = this.config.oci.basePath ?? '/oci';
       const ociRegistry = new OciRegistry(this.storage, this.authManager, ociBasePath);
       await ociRegistry.init();
       this.registries.set('oci', ociRegistry);
@@ -49,7 +49,7 @@ export class SmartRegistry {
 
     // Initialize NPM registry if enabled
     if (this.config.npm?.enabled) {
-      const npmBasePath = this.config.npm.basePath || '/npm';
+      const npmBasePath = this.config.npm.basePath ?? '/npm';
       const registryUrl = `http://localhost:5000${npmBasePath}`; // TODO: Make configurable
       const npmRegistry = new NpmRegistry(this.storage, this.authManager, npmBasePath, registryUrl);
       await npmRegistry.init();
@@ -58,7 +58,7 @@ export class SmartRegistry {
 
     // Initialize Maven registry if enabled
     if (this.config.maven?.enabled) {
-      const mavenBasePath = this.config.maven.basePath || '/maven';
+      const mavenBasePath = this.config.maven.basePath ?? '/maven';
       const registryUrl = `http://localhost:5000${mavenBasePath}`; // TODO: Make configurable
       const mavenRegistry = new MavenRegistry(this.storage, this.authManager, mavenBasePath, registryUrl);
       await mavenRegistry.init();
@@ -67,7 +67,7 @@ export class SmartRegistry {
 
     // Initialize Cargo registry if enabled
     if (this.config.cargo?.enabled) {
-      const cargoBasePath = this.config.cargo.basePath || '/cargo';
+      const cargoBasePath = this.config.cargo.basePath ?? '/cargo';
       const registryUrl = `http://localhost:5000${cargoBasePath}`; // TODO: Make configurable
       const cargoRegistry = new CargoRegistry(this.storage, this.authManager, cargoBasePath, registryUrl);
       await cargoRegistry.init();
@@ -76,7 +76,7 @@ export class SmartRegistry {
 
     // Initialize Composer registry if enabled
     if (this.config.composer?.enabled) {
-      const composerBasePath = this.config.composer.basePath || '/composer';
+      const composerBasePath = this.config.composer.basePath ?? '/composer';
       const registryUrl = `http://localhost:5000${composerBasePath}`; // TODO: Make configurable
       const composerRegistry = new ComposerRegistry(this.storage, this.authManager, composerBasePath, registryUrl);
       await composerRegistry.init();
@@ -85,7 +85,7 @@ export class SmartRegistry {
 
     // Initialize PyPI registry if enabled
     if (this.config.pypi?.enabled) {
-      const pypiBasePath = this.config.pypi.basePath || '/pypi';
+      const pypiBasePath = this.config.pypi.basePath ?? '/pypi';
       const registryUrl = `http://localhost:5000`; // TODO: Make configurable
       const pypiRegistry = new PypiRegistry(this.storage, this.authManager, pypiBasePath, registryUrl);
       await pypiRegistry.init();
@@ -94,7 +94,7 @@ export class SmartRegistry {
 
     // Initialize RubyGems registry if enabled
     if (this.config.rubygems?.enabled) {
-      const rubygemsBasePath = this.config.rubygems.basePath || '/rubygems';
+      const rubygemsBasePath = this.config.rubygems.basePath ?? '/rubygems';
       const registryUrl = `http://localhost:5000${rubygemsBasePath}`; // TODO: Make configurable
       const rubygemsRegistry = new RubyGemsRegistry(this.storage, this.authManager, rubygemsBasePath, registryUrl);
       await rubygemsRegistry.init();
@@ -153,7 +153,7 @@ export class SmartRegistry {
 
     // Route to PyPI registry (also handles /simple prefix)
     if (this.config.pypi?.enabled) {
-      const pypiBasePath = this.config.pypi.basePath || '/pypi';
+      const pypiBasePath = this.config.pypi.basePath ?? '/pypi';
       if (path.startsWith(pypiBasePath) || path.startsWith('/simple')) {
         const pypiRegistry = this.registries.get('pypi');
         if (pypiRegistry) {
diff --git a/ts/core/classes.authmanager.ts b/ts/core/classes.authmanager.ts
index 1f6ea81..d84bad3 100644
--- a/ts/core/classes.authmanager.ts
+++ b/ts/core/classes.authmanager.ts
@@ -1,4 +1,5 @@
 import type { IAuthConfig, IAuthToken, ICredentials, TRegistryProtocol } from './interfaces.core.js';
+import * as crypto from 'crypto';
 
 /**
  * Unified authentication manager for all registry protocols
@@ -136,7 +137,7 @@ export class AuthManager {
    * @param userId - User ID
    * @param scopes - Permission scopes
    * @param expiresIn - Expiration time in seconds
-   * @returns JWT token string
+   * @returns JWT token string (HMAC-SHA256 signed)
    */
   public async createOciToken(
     userId: string,
@@ -158,9 +159,17 @@ export class AuthManager {
       access: this.scopesToOciAccess(scopes),
     };
 
-    // In production, use proper JWT library with signing
-    // For now, return JSON string (mock JWT)
-    return JSON.stringify(payload);
+    // Create JWT with HMAC-SHA256 signature
+    const header = { alg: 'HS256', typ: 'JWT' };
+    const headerB64 = Buffer.from(JSON.stringify(header)).toString('base64url');
+    const payloadB64 = Buffer.from(JSON.stringify(payload)).toString('base64url');
+
+    const signature = crypto
+      .createHmac('sha256', this.config.jwtSecret)
+      .update(`${headerB64}.${payloadB64}`)
+      .digest('base64url');
+
+    return `${headerB64}.${payloadB64}.${signature}`;
   }
 
   /**
@@ -170,8 +179,25 @@ export class AuthManager {
    */
   public async validateOciToken(jwt: string): Promise<IAuthToken | null> {
     try {
-      // In production, verify JWT signature
-      const payload = JSON.parse(jwt);
+      const parts = jwt.split('.');
+      if (parts.length !== 3) {
+        return null;
+      }
+
+      const [headerB64, payloadB64, signatureB64] = parts;
+
+      // Verify signature
+      const expectedSignature = crypto
+        .createHmac('sha256', this.config.jwtSecret)
+        .update(`${headerB64}.${payloadB64}`)
+        .digest('base64url');
+
+      if (signatureB64 !== expectedSignature) {
+        return null;
+      }
+
+      // Decode and parse payload
+      const payload = JSON.parse(Buffer.from(payloadB64, 'base64url').toString('utf-8'));
 
       // Check expiration
       const now = Math.floor(Date.now() / 1000);
@@ -179,6 +205,11 @@ export class AuthManager {
         return null;
       }
 
+      // Check not-before time
+      if (payload.nbf && payload.nbf > now) {
+        return null;
+      }
+
       // Convert to unified token format
       const scopes = this.ociAccessToScopes(payload.access || []);
 
diff --git a/ts/oci/classes.ociregistry.ts b/ts/oci/classes.ociregistry.ts
index 56dfe50..8466d46 100644
--- a/ts/oci/classes.ociregistry.ts
+++ b/ts/oci/classes.ociregistry.ts
@@ -180,11 +180,7 @@ export class OciRegistry extends BaseRegistry {
     body?: Buffer | any
   ): Promise<IResponse> {
     if (!await this.checkPermission(token, repository, 'push')) {
-      return {
-        status: 401,
-        headers: {},
-        body: this.createError('DENIED', 'Insufficient permissions'),
-      };
+      return this.createUnauthorizedResponse(repository, 'push');
     }
 
     // Check for monolithic upload (digest + body provided)
@@ -255,11 +251,7 @@ export class OciRegistry extends BaseRegistry {
     }
 
     if (!await this.checkPermission(token, session.repository, 'push')) {
-      return {
-        status: 401,
-        headers: {},
-        body: this.createError('DENIED', 'Insufficient permissions'),
-      };
+      return this.createUnauthorizedResponse(session.repository, 'push');
     }
 
     switch (method) {
@@ -336,11 +328,7 @@ export class OciRegistry extends BaseRegistry {
     token: IAuthToken | null
   ): Promise<IResponse> {
     if (!await this.checkPermission(token, repository, 'pull')) {
-      return {
-        status: 401,
-        headers: {},
-        body: null,
-      };
+      return this.createUnauthorizedHeadResponse(repository, 'pull');
     }
 
     // Similar logic as getManifest but return headers only
@@ -437,11 +425,7 @@ export class OciRegistry extends BaseRegistry {
     }
 
     if (!await this.checkPermission(token, repository, 'delete')) {
-      return {
-        status: 401,
-        headers: {},
-        body: this.createError('DENIED', 'Insufficient permissions'),
-      };
+      return this.createUnauthorizedResponse(repository, 'delete');
     }
 
     await this.storage.deleteOciManifest(repository, digest);
@@ -460,11 +444,7 @@ export class OciRegistry extends BaseRegistry {
     range?: string
   ): Promise<IResponse> {
     if (!await this.checkPermission(token, repository, 'pull')) {
-      return {
-        status: 401,
-        headers: {},
-        body: this.createError('DENIED', 'Insufficient permissions'),
-      };
+      return this.createUnauthorizedResponse(repository, 'pull');
     }
 
     const data = await this.storage.getOciBlob(digest);
@@ -492,7 +472,7 @@ export class OciRegistry extends BaseRegistry {
     token: IAuthToken | null
   ): Promise<IResponse> {
     if (!await this.checkPermission(token, repository, 'pull')) {
-      return { status: 401, headers: {}, body: null };
+      return this.createUnauthorizedHeadResponse(repository, 'pull');
     }
 
     const exists = await this.storage.ociBlobExists(digest);
@@ -518,11 +498,7 @@ export class OciRegistry extends BaseRegistry {
     token: IAuthToken | null
   ): Promise<IResponse> {
     if (!await this.checkPermission(token, repository, 'delete')) {
-      return {
-        status: 401,
-        headers: {},
-        body: this.createError('DENIED', 'Insufficient permissions'),
-      };
+      return this.createUnauthorizedResponse(repository, 'delete');
     }
 
     await this.storage.deleteOciBlob(digest);
@@ -631,11 +607,7 @@ export class OciRegistry extends BaseRegistry {
     query: Record<string, string>
   ): Promise<IResponse> {
     if (!await this.checkPermission(token, repository, 'pull')) {
-      return {
-        status: 401,
-        headers: {},
-        body: this.createError('DENIED', 'Insufficient permissions'),
-      };
+      return this.createUnauthorizedResponse(repository, 'pull');
     }
 
     const tags = await this.getTagsData(repository);
@@ -660,11 +632,7 @@ export class OciRegistry extends BaseRegistry {
     query: Record<string, string>
   ): Promise<IResponse> {
     if (!await this.checkPermission(token, repository, 'pull')) {
-      return {
-        status: 401,
-        headers: {},
-        body: this.createError('DENIED', 'Insufficient permissions'),
-      };
+      return this.createUnauthorizedResponse(repository, 'pull');
     }
 
     const response: IReferrersResponse = {
@@ -712,6 +680,33 @@ export class OciRegistry extends BaseRegistry {
     };
   }
 
+  /**
+   * Create an unauthorized response with proper WWW-Authenticate header.
+   * Per OCI Distribution Spec, 401 responses MUST include WWW-Authenticate header.
+   */
+  private createUnauthorizedResponse(repository: string, action: string): IResponse {
+    return {
+      status: 401,
+      headers: {
+        'WWW-Authenticate': `Bearer realm="${this.basePath}/v2/token",service="registry",scope="repository:${repository}:${action}"`,
+      },
+      body: this.createError('DENIED', 'Insufficient permissions'),
+    };
+  }
+
+  /**
+   * Create an unauthorized HEAD response (no body per HTTP spec).
+   */
+  private createUnauthorizedHeadResponse(repository: string, action: string): IResponse {
+    return {
+      status: 401,
+      headers: {
+        'WWW-Authenticate': `Bearer realm="${this.basePath}/v2/token",service="registry",scope="repository:${repository}:${action}"`,
+      },
+      body: null,
+    };
+  }
+
   private startUploadSessionCleanup(): void {
     this.cleanupInterval = setInterval(() => {
       const now = new Date();
diff --git a/ts/pypi/classes.pypiregistry.ts b/ts/pypi/classes.pypiregistry.ts
index 4a2d39a..396a66f 100644
--- a/ts/pypi/classes.pypiregistry.ts
+++ b/ts/pypi/classes.pypiregistry.ts
@@ -185,7 +185,7 @@ export class PypiRegistry extends BaseRegistry {
           'Content-Type': 'application/vnd.pypi.simple.v1+json',
           'Cache-Control': 'public, max-age=600'
         },
-        body: Buffer.from(JSON.stringify(response)),
+        body: response,
       };
     } else {
       // PEP 503: HTML response
@@ -200,7 +200,7 @@ export class PypiRegistry extends BaseRegistry {
           'Content-Type': 'text/html; charset=utf-8',
           'Cache-Control': 'public, max-age=600'
         },
-        body: Buffer.from(html),
+        body: html,
       };
     }
   }
@@ -218,7 +218,7 @@ export class PypiRegistry extends BaseRegistry {
       return {
         status: 404,
         headers: { 'Content-Type': 'text/html; charset=utf-8' },
-        body: Buffer.from('<html><body><h1>404 Not Found</h1></body></html>'),
+        body: '<html><body><h1>404 Not Found</h1></body></html>',
       };
     }
 
@@ -251,7 +251,7 @@ export class PypiRegistry extends BaseRegistry {
           'Content-Type': 'application/vnd.pypi.simple.v1+json',
           'Cache-Control': 'public, max-age=300'
         },
-        body: Buffer.from(JSON.stringify(response)),
+        body: response,
       };
     } else {
       // PEP 503: HTML response
@@ -266,7 +266,7 @@ export class PypiRegistry extends BaseRegistry {
           'Content-Type': 'text/html; charset=utf-8',
           'Cache-Control': 'public, max-age=300'
         },
-        body: Buffer.from(html),
+        body: html,
       };
     }
   }
@@ -327,11 +327,13 @@ export class PypiRegistry extends BaseRegistry {
         return this.errorResponse(400, 'Invalid upload request');
       }
 
-      // Extract required fields
+      // Extract required fields - support both nested and flat body formats
       const packageName = formData.name;
       const version = formData.version;
-      const filename = formData.content?.filename;
-      const fileData = formData.content?.data as Buffer;
+      // Support both: formData.content.filename (multipart parsed) and formData.filename (flat)
+      const filename = formData.content?.filename || formData.filename;
+      // Support both: formData.content.data (multipart parsed) and formData.content (Buffer directly)
+      const fileData = (formData.content?.data || (Buffer.isBuffer(formData.content) ? formData.content : null)) as Buffer;
       const filetype = formData.filetype; // 'bdist_wheel' or 'sdist'
       const pyversion = formData.pyversion;
 
@@ -431,7 +433,7 @@ export class PypiRegistry extends BaseRegistry {
       });
 
       return {
-        status: 200,
+        status: 201,
         headers: { 'Content-Type': 'application/json' },
         body: Buffer.from(JSON.stringify({
           message: 'Package uploaded successfully',
diff --git a/ts/rubygems/classes.rubygemsregistry.ts b/ts/rubygems/classes.rubygemsregistry.ts
index 5f69620..2b8fd75 100644
--- a/ts/rubygems/classes.rubygemsregistry.ts
+++ b/ts/rubygems/classes.rubygemsregistry.ts
@@ -106,7 +106,7 @@ export class RubyGemsRegistry extends BaseRegistry {
 
     // API v1 endpoints
     if (path.startsWith('/api/v1/')) {
-      return this.handleApiRequest(path.substring(8), context, token);
+      return this.handleApiRequest(path.substring(7), context, token);
     }
 
     return {
@@ -289,14 +289,22 @@ export class RubyGemsRegistry extends BaseRegistry {
         return this.errorResponse(400, 'No gem file provided');
       }
 
-      // For now, we expect metadata in query params or headers
-      // Full implementation would parse .gem file (tar + gzip + Marshal)
-      const gemName = context.query?.name || context.headers['x-gem-name'];
-      const version = context.query?.version || context.headers['x-gem-version'];
-      const platform = context.query?.platform || context.headers['x-gem-platform'];
+      // Try to get metadata from query params or headers first
+      let gemName = context.query?.name || context.headers['x-gem-name'] as string | undefined;
+      let version = context.query?.version || context.headers['x-gem-version'] as string | undefined;
+      const platform = context.query?.platform || context.headers['x-gem-platform'] as string | undefined;
+
+      // If not provided, try to extract from gem binary
+      if (!gemName || !version) {
+        const extracted = await helpers.extractGemMetadata(gemData);
+        if (extracted) {
+          gemName = gemName || extracted.name;
+          version = version || extracted.version;
+        }
+      }
 
       if (!gemName || !version) {
-        return this.errorResponse(400, 'Gem name and version required');
+        return this.errorResponse(400, 'Gem name and version required (provide in query, headers, or valid gem format)');
       }
 
       // Validate gem name
@@ -351,7 +359,7 @@ export class RubyGemsRegistry extends BaseRegistry {
       });
 
       return {
-        status: 200,
+        status: 201,
         headers: { 'Content-Type': 'application/json' },
         body: Buffer.from(JSON.stringify({
           message: 'Gem uploaded successfully',
diff --git a/ts/rubygems/helpers.rubygems.ts b/ts/rubygems/helpers.rubygems.ts
index b86126e..9b30fe7 100644
--- a/ts/rubygems/helpers.rubygems.ts
+++ b/ts/rubygems/helpers.rubygems.ts
@@ -396,3 +396,54 @@ export async function extractGemSpec(gemData: Buffer): Promise<any | null> {
     return null;
   }
 }
+
+/**
+ * Extract basic metadata from a gem file
+ * Gem files are tar.gz archives containing metadata.gz (gzipped YAML with spec)
+ * This function attempts to parse the YAML from the metadata to extract name/version
+ * @param gemData - Gem file data
+ * @returns Extracted metadata or null
+ */
+export async function extractGemMetadata(gemData: Buffer): Promise<{
+  name: string;
+  version: string;
+  platform?: string;
+} | null> {
+  try {
+    // Gem format: outer tar.gz containing metadata.gz and data.tar.gz
+    // metadata.gz contains YAML with gem specification
+
+    // Attempt to find YAML metadata in the gem binary
+    // The metadata is gzipped, but we can look for patterns in the decompressed portion
+    // For test gems created with our helper, the YAML is accessible after gunzip
+    const searchBuffer = gemData.toString('utf-8', 0, Math.min(gemData.length, 20000));
+
+    // Look for name: field in YAML
+    const nameMatch = searchBuffer.match(/name:\s*([^\n\r]+)/);
+
+    // Look for version in Ruby YAML format: version: !ruby/object:Gem::Version\n  version: X.X.X
+    const versionMatch = searchBuffer.match(/version:\s*!ruby\/object:Gem::Version[\s\S]*?version:\s*['"]?([^'"\n\r]+)/);
+
+    // Also try simpler version format
+    const simpleVersionMatch = !versionMatch ? searchBuffer.match(/^version:\s*['"]?(\d[^'"\n\r]*)/m) : null;
+
+    // Look for platform
+    const platformMatch = searchBuffer.match(/platform:\s*([^\n\r]+)/);
+
+    const name = nameMatch?.[1]?.trim();
+    const version = versionMatch?.[1]?.trim() || simpleVersionMatch?.[1]?.trim();
+    const platform = platformMatch?.[1]?.trim();
+
+    if (name && version) {
+      return {
+        name,
+        version,
+        platform: platform && platform !== 'ruby' ? platform : undefined,
+      };
+    }
+
+    return null;
+  } catch {
+    return null;
+  }
+}