diff --git a/vscode/src/ruby.ts b/vscode/src/ruby.ts
index 42e190bc4..f06786d83 100644
--- a/vscode/src/ruby.ts
+++ b/vscode/src/ruby.ts
@@ -51,15 +51,18 @@ export class Ruby implements RubyInterface {
   private readonly context: vscode.ExtensionContext;
   private readonly customBundleGemfile?: string;
   private readonly outputChannel: WorkspaceChannel;
+  private readonly telemetry: vscode.TelemetryLogger;
 
   constructor(
     context: vscode.ExtensionContext,
     workspaceFolder: vscode.WorkspaceFolder,
     outputChannel: WorkspaceChannel,
+    telemetry: vscode.TelemetryLogger,
   ) {
     this.context = context;
     this.workspaceFolder = workspaceFolder;
     this.outputChannel = outputChannel;
+    this.telemetry = telemetry;
 
     const customBundleGemfile: string = vscode.workspace
       .getConfiguration("rubyLsp")
@@ -125,6 +128,10 @@ export class Ruby implements RubyInterface {
       try {
         await this.runManagerActivation();
       } catch (error: any) {
+        this.telemetry.logError(error, {
+          versionManager: this.versionManager.identifier,
+        });
+
         // If an error occurred and a global Ruby path is configured, then we can try to fallback to that
         const globalRubyPath = vscode.workspace
           .getConfiguration("rubyLsp")
diff --git a/vscode/src/test/suite/client.test.ts b/vscode/src/test/suite/client.test.ts
index 687c243dd..15dd1317d 100644
--- a/vscode/src/test/suite/client.test.ts
+++ b/vscode/src/test/suite/client.test.ts
@@ -138,7 +138,12 @@ async function launchClient(workspaceUri: vscode.Uri) {
     }
   }
 
-  const ruby = new Ruby(context, workspaceFolder, outputChannel);
+  const ruby = new Ruby(
+    context,
+    workspaceFolder,
+    outputChannel,
+    FAKE_TELEMETRY,
+  );
   await ruby.activateRuby();
   ruby.env.RUBY_LSP_BYPASS_TYPECHECKER = "true";
 
diff --git a/vscode/src/test/suite/debugger.test.ts b/vscode/src/test/suite/debugger.test.ts
index efa1338e5..ac22c0c8a 100644
--- a/vscode/src/test/suite/debugger.test.ts
+++ b/vscode/src/test/suite/debugger.test.ts
@@ -13,6 +13,8 @@ import { WorkspaceChannel } from "../../workspaceChannel";
 import { LOG_CHANNEL, asyncExec } from "../../common";
 import { RUBY_VERSION } from "../rubyVersion";
 
+import { FAKE_TELEMETRY } from "./fakeTelemetry";
+
 suite("Debugger", () => {
   test("Provide debug configurations returns the default configs", () => {
     const context = { subscriptions: [] } as unknown as vscode.ExtensionContext;
@@ -203,7 +205,12 @@ suite("Debugger", () => {
       name: path.basename(tmpPath),
       index: 0,
     };
-    const ruby = new Ruby(context, workspaceFolder, outputChannel);
+    const ruby = new Ruby(
+      context,
+      workspaceFolder,
+      outputChannel,
+      FAKE_TELEMETRY,
+    );
     await ruby.activateRuby();
 
     try {
diff --git a/vscode/src/test/suite/ruby.test.ts b/vscode/src/test/suite/ruby.test.ts
index 5180c8049..b3832b439 100644
--- a/vscode/src/test/suite/ruby.test.ts
+++ b/vscode/src/test/suite/ruby.test.ts
@@ -11,6 +11,8 @@ import { LOG_CHANNEL } from "../../common";
 import * as common from "../../common";
 import { ACTIVATION_SEPARATOR } from "../../ruby/versionManager";
 
+import { FAKE_TELEMETRY } from "./fakeTelemetry";
+
 suite("Ruby environment activation", () => {
   const workspacePath = path.dirname(
     path.dirname(path.dirname(path.dirname(__dirname))),
@@ -48,7 +50,12 @@ suite("Ruby environment activation", () => {
         },
       } as unknown as vscode.WorkspaceConfiguration);
 
-    const ruby = new Ruby(context, workspaceFolder, outputChannel);
+    const ruby = new Ruby(
+      context,
+      workspaceFolder,
+      outputChannel,
+      FAKE_TELEMETRY,
+    );
     await ruby.activateRuby();
 
     assert.ok(ruby.rubyVersion, "Expected Ruby version to be set");
@@ -80,7 +87,12 @@ suite("Ruby environment activation", () => {
         },
       } as unknown as vscode.WorkspaceConfiguration);
 
-    const ruby = new Ruby(context, workspaceFolder, outputChannel);
+    const ruby = new Ruby(
+      context,
+      workspaceFolder,
+      outputChannel,
+      FAKE_TELEMETRY,
+    );
 
     process.env.VERBOSE = "1";
     process.env.DEBUG = "WARN";
@@ -123,7 +135,12 @@ suite("Ruby environment activation", () => {
       stderr: `${ACTIVATION_SEPARATOR}${JSON.stringify(envStub)}${ACTIVATION_SEPARATOR}`,
     });
 
-    const ruby = new Ruby(context, workspaceFolder, outputChannel);
+    const ruby = new Ruby(
+      context,
+      workspaceFolder,
+      outputChannel,
+      FAKE_TELEMETRY,
+    );
     await ruby.activateRuby();
     execStub.restore();
     configStub.restore();
diff --git a/vscode/src/workspace.ts b/vscode/src/workspace.ts
index ef70d4117..98e6fc4db 100644
--- a/vscode/src/workspace.ts
+++ b/vscode/src/workspace.ts
@@ -44,7 +44,12 @@ export class Workspace implements WorkspaceInterface {
       LOG_CHANNEL,
     );
     this.telemetry = telemetry;
-    this.ruby = new Ruby(context, workspaceFolder, this.outputChannel);
+    this.ruby = new Ruby(
+      context,
+      workspaceFolder,
+      this.outputChannel,
+      telemetry,
+    );
     this.createTestItems = createTestItems;
     this.isMainWorkspace = isMainWorkspace;
     this.virtualDocuments = virtualDocuments;