diff --git a/vscode/package.json b/vscode/package.json
index 24ebbf4086..a4f290d976 100644
--- a/vscode/package.json
+++ b/vscode/package.json
@@ -253,6 +253,10 @@
             "miseExecutablePath": {
               "description": "The path to the Mise executable, if not installed in ~/.local/bin/mise",
               "type": "string"
+            },
+            "chrubyRubies": {
+              "description": "An array of extra directories to search for Ruby installations when using chruby. Equivalent to the RUBIES environment variable",
+              "type": "array"
             }
           },
           "default": {
diff --git a/vscode/src/ruby/chruby.ts b/vscode/src/ruby/chruby.ts
index 6f863de741..1d6ac0e248 100644
--- a/vscode/src/ruby/chruby.ts
+++ b/vscode/src/ruby/chruby.ts
@@ -5,6 +5,7 @@ import path from "path";
 import * as vscode from "vscode";
 
 import { asyncExec } from "../common";
+import { WorkspaceChannel } from "../workspaceChannel";
 
 import { ActivationResult, VersionManager } from "./versionManager";
 
@@ -22,6 +23,23 @@ export class Chruby extends VersionManager {
     vscode.Uri.joinPath(vscode.Uri.file(os.homedir()), ".rubies"),
   ];
 
+  constructor(
+    workspaceFolder: vscode.WorkspaceFolder,
+    outputChannel: WorkspaceChannel,
+  ) {
+    super(workspaceFolder, outputChannel);
+
+    const configuredRubies = vscode.workspace
+      .getConfiguration("rubyLsp")
+      .get<string[] | undefined>("rubyVersionManager.chrubyRubies");
+
+    if (configuredRubies) {
+      this.rubyInstallationUris.push(
+        ...configuredRubies.map((path) => vscode.Uri.file(path)),
+      );
+    }
+  }
+
   async activate(): Promise<ActivationResult> {
     const versionInfo = await this.discoverRubyVersion();
     const rubyUri = await this.findRubyUri(versionInfo);
@@ -72,7 +90,8 @@ export class Chruby extends VersionManager {
     }
 
     throw new Error(
-      `Cannot find installation directory for Ruby version ${possibleVersionNames.join(" or ")}`,
+      `Cannot find installation directory for Ruby version ${possibleVersionNames.join(" or ")}.
+       Searched in ${this.rubyInstallationUris.map((uri) => uri.fsPath).join(", ")}`,
     );
   }
 
diff --git a/vscode/src/test/suite/ruby/chruby.test.ts b/vscode/src/test/suite/ruby/chruby.test.ts
index cd4cd8add5..2078b7e900 100644
--- a/vscode/src/test/suite/ruby/chruby.test.ts
+++ b/vscode/src/test/suite/ruby/chruby.test.ts
@@ -6,6 +6,7 @@ import os from "os";
 
 import { before, after } from "mocha";
 import * as vscode from "vscode";
+import sinon from "sinon";
 
 import { Chruby } from "../../../ruby/chruby";
 import { WorkspaceChannel } from "../../../workspaceChannel";
@@ -157,4 +158,23 @@ suite("Chruby", () => {
     assert.strictEqual(version, RUBY_VERSION);
     assert.notStrictEqual(yjit, undefined);
   });
+
+  test("Finds Ruby when extra RUBIES are configured", async () => {
+    fs.writeFileSync(path.join(workspacePath, ".ruby-version"), RUBY_VERSION);
+
+    const chruby = new Chruby(workspaceFolder, outputChannel);
+    const configStub = sinon
+      .stub(vscode.workspace, "getConfiguration")
+      .returns({
+        get: () => [path.join(rootPath, "opt", "rubies")],
+      } as any);
+
+    const { env, version, yjit } = await chruby.activate();
+    configStub.restore();
+
+    assert.match(env.GEM_PATH!, new RegExp(`ruby/${VERSION_REGEX}`));
+    assert.match(env.GEM_PATH!, new RegExp(`lib/ruby/gems/${VERSION_REGEX}`));
+    assert.strictEqual(version, RUBY_VERSION);
+    assert.notStrictEqual(yjit, undefined);
+  });
 });