diff --git a/CHANGELOG.md b/CHANGELOG.md
index 3f6b438..3af513d 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -7,6 +7,7 @@ The format is based on [Keep a Changelog](https://keepachangelog.com/), and this
 ## [Unreleased]
 
 ### Fixed
+- Use Shopify Ruby LSP for Ruby file launches, passing the command and file separately.
 - Startup failures now report the configured pre-launch task and exit code when available, preserve configuration and test-dispatch errors, and direct agents to launch/task diagnostics instead of assuming a missing language extension. Readiness waits are cancelled when startup fails.
 
 ## [2.3.4] - 2026-09-03
@@ -122,4 +123,4 @@ The format is based on [Keep a Changelog](https://keepachangelog.com/), and this
 - Initial release
 - Core debugging capabilities via MCP protocol
 - VS Code Debug Adapter Protocol integration
-- Automatic MCP server startup on extension activation
\ No newline at end of file
+- Automatic MCP server startup on extension activation
diff --git a/README.md b/README.md
index 15a5bd8..b208050 100644
--- a/README.md
+++ b/README.md
@@ -154,7 +154,7 @@ DebugMCP supports debugging for the following languages with their respective VS
 | **Go** | [Go](https://marketplace.visualstudio.com/items?itemName=golang.Go) | `.go` | ✅ Fully Supported |
 | **Rust** | [rust-analyzer](https://marketplace.visualstudio.com/items?itemName=rust-lang.rust-analyzer) | `.rs` | ✅ Fully Supported |
 | **PHP** | [PHP Debug](https://marketplace.visualstudio.com/items?itemName=xdebug.php-debug) | `.php` | ✅ Fully Supported |
-| **Ruby** | [Ruby](https://marketplace.visualstudio.com/items?itemName=rebornix.ruby) | `.rb` | ✅ Fully Supported |
+| **Ruby** | [Ruby](https://marketplace.visualstudio.com/items?itemName=Shopify.ruby-lsp) | `.rb` | ✅ Fully Supported |
 | **C#/.NET** | [C#](https://marketplace.visualstudio.com/items?itemName=ms-dotnettools.csharp) | `.cs`, `.csproj` | ✅ Fully Supported |
 
 ## Configuration
@@ -428,7 +428,7 @@ The extension handles debug configurations intelligently:
   - **Go**: [Go extension](vscode:extension/golang.go)
   - **Rust**: [rust-analyzer extension](vscode:extension/rust-lang.rust-analyzer)
   - **PHP**: [PHP Debug extension](vscode:extension/xdebug.php-debug)
-  - **Ruby**: [Ruby extension](vscode:extension/rebornix.ruby) with debug support
+  - **Ruby**: [Ruby extension](vscode:extension/Shopify.ruby-lsp) and the [`debug` gem](https://github.com/ruby/debug)
 - MCP-compatible AI assistant (Copilot, Cline, Cursor, Codex, Windsurf, Roo Code, etc.)
 
 ## Development
@@ -499,4 +499,4 @@ If DebugMCP has helped you debug faster, please consider giving it a star on Git
 
 MIT License - See [LICENSE](LICENSE.txt) for details
 
-This extension was created by **Oz Zafar**, **Ori Bar-Ilan** and **Karin Brisker**.
\ No newline at end of file
+This extension was created by **Oz Zafar**, **Ori Bar-Ilan** and **Karin Brisker**.
diff --git a/docs/architecture/debugConfigurationManager.md b/docs/architecture/debugConfigurationManager.md
index 81d8349..f67d873 100644
--- a/docs/architecture/debugConfigurationManager.md
+++ b/docs/architecture/debugConfigurationManager.md
@@ -17,6 +17,7 @@ Delegating to those mechanisms keeps this class small and ensures defaults stay
 
 - Return a launch.json configuration name when the caller provides one — VS Code looks it up itself.
 - Otherwise, return a minimal launch stub (`type`, `request`, `name`, `program`) for the file's language and let the language extension resolve the rest.
+- For Ruby, select Shopify Ruby LSP's `ruby_lsp` adapter and pass `command: 'ruby'` and `file` separately so the adapter quotes the path.
 - For `.NET` (`coreclr`), locate the project's built DLL since `program` cannot be a `.cs` source file.
 - Detect the debugger `type` from a file extension.
 
@@ -39,7 +40,7 @@ Maps file extensions to debugger `type` values:
 - `.go` → `go`
 - `.rs` → `lldb`
 - `.php` → `php`
-- `.rb` → `ruby`
+- `.rb` → `ruby_lsp`
 
 ### Test framework support
 
@@ -49,7 +50,8 @@ Test launches are dispatched via `DebuggingExecutor.debugTestAtCursor`, not via
 
 1. If `configurationName` is provided and is not the sentinel `Default Configuration`, return that name verbatim.
 2. Otherwise, if the file is C# (`coreclr`), walk up to find the `.csproj`, locate its built DLL under `bin/{Debug,Release}/<tfm>/`, and return a coreclr config pointing at that assembly.
-3. Otherwise, return `{ type, request: 'launch', name: 'DebugMCP Launch', program: fileFullPath }`.
+3. For Ruby (`ruby_lsp`), return `{ type, request: 'launch', name: 'DebugMCP Launch', command: 'ruby', file: fileFullPath }`.
+4. Otherwise, return `{ type, request: 'launch', name: 'DebugMCP Launch', program: fileFullPath }`.
 
 ## Key code locations
 
diff --git a/skills/debug-live/README.md b/skills/debug-live/README.md
index a4eef19..462a70e 100644
--- a/skills/debug-live/README.md
+++ b/skills/debug-live/README.md
@@ -28,7 +28,8 @@ skills/debugmcp/
         ├── java.md
         ├── csharp.md
         ├── cpp.md
-        └── go.md
+        ├── go.md
+        └── ruby.md
 ```
 
 ## Installation
diff --git a/skills/debug-live/SKILL.md b/skills/debug-live/SKILL.md
index 41d7ea0..cf66b61 100644
--- a/skills/debug-live/SKILL.md
+++ b/skills/debug-live/SKILL.md
@@ -16,6 +16,7 @@ allowed-tools:
   - step_out
   - continue_execution
   - pause_execution
+  - get_debug_status
   - list_variable_names
   - get_variables_values
   - evaluate_expression
@@ -232,6 +233,7 @@ Load the relevant reference file for the language you're debugging:
 - **C#** → `references/troubleshooting/csharp.md`
 - **C++** → `references/troubleshooting/cpp.md`
 - **Go** → `references/troubleshooting/go.md`
+- **Ruby** → `references/troubleshooting/ruby.md`
 
 Each reference covers prerequisites (which VS Code extension to install), framework-specific
 configuration (e.g. enabling `pytest` test discovery, building `.NET` projects before
diff --git a/skills/debug-live/references/troubleshooting/ruby.md b/skills/debug-live/references/troubleshooting/ruby.md
new file mode 100644
index 0000000..e064f59
--- /dev/null
+++ b/skills/debug-live/references/troubleshooting/ruby.md
@@ -0,0 +1,77 @@
+# Ruby Debugging Tips
+
+## Prerequisites
+
+- Install the [Shopify Ruby LSP](https://marketplace.visualstudio.com/items?itemName=Shopify.ruby-lsp) extension.
+- Add Ruby's official [`debug`](https://github.com/ruby/debug) gem to the project bundle. With Bundler, verify that the
+  selected Ruby can run it with `bundle exec rdbg -v`.
+- Make sure Ruby LSP activates the same Ruby version and bundle as the application. If automatic detection selects the
+  wrong runtime, configure `rubyLsp.rubyVersionManager` and restart Ruby LSP.
+
+DebugMCP uses the `ruby_lsp` debug adapter for `.rb` files. Do not install or configure the deprecated
+`rebornix.ruby` adapter for this workflow.
+
+## Ruby scripts
+
+For an ordinary Ruby script, set a breakpoint on an executable line and call `start_debugging` with the script path and
+the project root. DebugMCP creates a minimal Ruby LSP launch configuration and passes the Ruby command and file
+separately, so paths containing spaces or shell metacharacters remain valid.
+
+Use a named `launch.json` configuration only when the program needs a specific command, environment, or attach mode:
+
+```json
+{
+  "type": "ruby_lsp",
+  "request": "launch",
+  "name": "Debug Rails",
+  "program": "bin/rails server"
+}
+```
+
+Pass its name as `configurationName` to `start_debugging`.
+
+## Rails and long-running processes
+
+For a Rails request, job, or callback, set the breakpoint before starting the debug session and make sure the request or
+job is triggered in the process launched by the debugger. A breakpoint in a web process will not catch code executed by
+a separate Sidekiq process, Puma worker, test process, container, or preloader.
+
+To attach to a Rails server instead of launching a new one, start it with the official debugger and use a named
+`ruby_lsp` attach configuration:
+
+```text
+bundle exec rdbg -O -n -c -- bin/rails server
+```
+
+```json
+{
+  "type": "ruby_lsp",
+  "request": "attach",
+  "name": "Attach to Ruby"
+}
+```
+
+Then pass `configurationName: "Attach to Ruby"` to `start_debugging`. Keep the debugger endpoint local unless the
+project has an explicit, secured remote-debugging setup.
+
+`start_debugging` returns as soon as the Ruby attach succeeds; it does not wait for a later request or job to hit the
+breakpoint. Trigger that work after the attach result, then call `get_debug_status` with `waitForPauseSeconds` to wait
+for the Ruby breakpoint without polling or interrupting the server with `pause_execution`. Inspect values only after
+the returned status is `paused`.
+
+## Common failures
+
+### The debugger does not start
+
+- Run `bundle exec rdbg -v` from `workingDirectory`.
+- Verify VS Code and Ruby LSP selected the project's intended Ruby and Gemfile.
+- Open the workspace at the directory that owns the bundle; incorrect workspace roots commonly select another runtime.
+- Restart Ruby LSP after changing gems, version-manager settings, or the bundle.
+
+### A breakpoint is not hit
+
+- Put it on an executable Ruby line, not a blank line, comment, method declaration terminator, or DSL line that ran
+  before the debugger attached.
+- Confirm the debugged process actually executes that file and code path.
+- Check for a different worker, preloader, container, generated copy, or mismatched local/remote source path.
+- For a long-running server, trigger the request or job only after the debugger session has started.
diff --git a/src/test/debugConfigurationManager.test.ts b/src/test/debugConfigurationManager.test.ts
new file mode 100644
index 0000000..7392a07
--- /dev/null
+++ b/src/test/debugConfigurationManager.test.ts
@@ -0,0 +1,32 @@
+// Copyright (c) Microsoft Corporation.
+
+import * as assert from 'assert';
+import { DebugConfigurationManager } from '../utils/debugConfigurationManager';
+
+suite('DebugConfigurationManager', () => {
+    const manager = new DebugConfigurationManager();
+
+    test('uses the Ruby LSP debug adapter for Ruby files', () => {
+        assert.strictEqual(manager.detectLanguageFromFilePath('/repo/example.rb'), 'ruby_lsp');
+    });
+
+    test('creates a Ruby LSP launch config with a separate command and file', async () => {
+        const fileFullPath = '/repo/with spaces/example.rb';
+
+        const config = await manager.getDebugConfig('/repo', fileFullPath);
+
+        assert.deepStrictEqual(config, {
+            type: 'ruby_lsp',
+            request: 'launch',
+            name: 'DebugMCP Launch',
+            command: 'ruby',
+            file: fileFullPath
+        });
+    });
+
+    test('preserves explicitly named launch configurations for Ruby', async () => {
+        const config = await manager.getDebugConfig('/repo', '/repo/example.rb', 'Debug Rails');
+
+        assert.strictEqual(config, 'Debug Rails');
+    });
+});
diff --git a/src/test/debugSkillGuidance.test.ts b/src/test/debugSkillGuidance.test.ts
index 4f363d9..a021bcb 100644
--- a/src/test/debugSkillGuidance.test.ts
+++ b/src/test/debugSkillGuidance.test.ts
@@ -7,8 +7,10 @@ import { suite, test } from 'mocha';
 
 suite('debug-live skill guidance', () => {
     const skillPath = path.resolve(__dirname, '..', '..', 'skills', 'debug-live', 'SKILL.md');
+    const rubyGuidancePath = path.resolve(__dirname, '..', '..', 'skills', 'debug-live', 'references', 'troubleshooting', 'ruby.md');
     const serverPath = path.resolve(__dirname, '..', '..', 'src', 'debugMCPServer.ts');
     const skill = fs.readFileSync(skillPath, 'utf8');
+    const rubyGuidance = fs.readFileSync(rubyGuidancePath, 'utf8');
     const serverSource = fs.readFileSync(serverPath, 'utf8');
     const description = skill.match(/^description:\s*(.+)$/m)?.[1] ?? '';
 
@@ -42,4 +44,10 @@ suite('debug-live skill guidance', () => {
     test('start_debugging points agents to the skill', () => {
         assert.match(serverSource, /Invoke the "debug-live" skill first\./);
     });
+
+    test('Ruby attach guidance waits for a breakpoint without interrupting the server', () => {
+        assert.match(skill, /^  - get_debug_status$/m);
+        assert.match(rubyGuidance, /`get_debug_status` with `waitForPauseSeconds`/);
+        assert.match(rubyGuidance, /without polling or interrupting the server with `pause_execution`/);
+    });
 });
diff --git a/src/test/startDebuggingMatrix.test.ts b/src/test/startDebuggingMatrix.test.ts
index 4d162d0..0d4b155 100644
--- a/src/test/startDebuggingMatrix.test.ts
+++ b/src/test/startDebuggingMatrix.test.ts
@@ -119,7 +119,8 @@ const LANGUAGES: LangCase[] = [
     { label: 'Java',       file: '/repo/src/App.java',        debuggerType: 'java'     },
     { label: 'C#',         file: '/repo/src/AppTests.cs',     debuggerType: 'coreclr'  },
     { label: 'C++',        file: '/repo/src/app.cpp',         debuggerType: 'cppdbg'   },
-    { label: 'Go',         file: '/repo/src/main.go',         debuggerType: 'go'       }
+    { label: 'Go',         file: '/repo/src/main.go',         debuggerType: 'go'       },
+    { label: 'Ruby',       file: '/repo/src/app.rb',          debuggerType: 'ruby_lsp' }
 ];
 
 suite('handleStartDebugging regression matrix', () => {
diff --git a/src/utils/debugConfigurationManager.ts b/src/utils/debugConfigurationManager.ts
index 096267d..54e4102 100644
--- a/src/utils/debugConfigurationManager.ts
+++ b/src/utils/debugConfigurationManager.ts
@@ -48,7 +48,7 @@ export class DebugConfigurationManager implements IDebugConfigurationManager {
         '.go': 'go',
         '.rs': 'lldb',
         '.php': 'php',
-        '.rb': 'ruby'
+        '.rb': 'ruby_lsp'
     };
 
     /**
@@ -75,6 +75,19 @@ export class DebugConfigurationManager implements IDebugConfigurationManager {
             return await this.createDotNetLaunchConfig(fileFullPath);
         }
 
+        // Ruby LSP accepts a command and file separately, then quotes the file
+        // when it builds the rdbg command. Keeping them separate avoids broken
+        // launches for paths containing spaces or shell metacharacters.
+        if (language === 'ruby_lsp') {
+            return {
+                type: language,
+                request: 'launch',
+                name: 'DebugMCP Launch',
+                command: 'ruby',
+                file: fileFullPath
+            };
+        }
+
         // Minimal stub. The language extension's resolveDebugConfiguration
         // fills in cwd, console, env, stopOnEntry, and other defaults.
         return {