diff --git a/vscode/src/test/suite/workspace.test.ts b/vscode/src/test/suite/workspace.test.ts
new file mode 100644
index 000000000..69b550019
--- /dev/null
+++ b/vscode/src/test/suite/workspace.test.ts
@@ -0,0 +1,80 @@
+/* eslint-disable no-process-env */
+import assert from "assert";
+import path from "path";
+import os from "os";
+import fs from "fs";
+
+import sinon from "sinon";
+import * as vscode from "vscode";
+import { beforeEach, afterEach } from "mocha";
+
+import { Workspace } from "../../workspace";
+
+import { FAKE_TELEMETRY } from "./fakeTelemetry";
+
+suite("Workspace", () => {
+  const context = {
+    extensionMode: vscode.ExtensionMode.Test,
+    subscriptions: [],
+    workspaceState: {
+      get: (_name: string) => undefined,
+      update: (_name: string, _value: any) => Promise.resolve(),
+    },
+  } as unknown as vscode.ExtensionContext;
+  let workspacePath: string;
+  let workspaceUri: vscode.Uri;
+  let workspaceFolder: vscode.WorkspaceFolder;
+
+  beforeEach(() => {
+    workspacePath = fs.mkdtempSync(
+      path.join(os.tmpdir(), "ruby-lsp-test-workspace-"),
+    );
+    workspaceUri = vscode.Uri.file(workspacePath);
+
+    workspaceFolder = {
+      uri: workspaceUri,
+      name: path.basename(workspacePath),
+      index: 0,
+    };
+  });
+
+  afterEach(() => {
+    fs.rmSync(workspacePath, { recursive: true, force: true });
+  });
+
+  test("repeated rebase steps don't trigger multiple restarts", async () => {
+    const gitDir = path.join(workspacePath, ".git");
+    fs.mkdirSync(gitDir);
+
+    const workspace = new Workspace(
+      context,
+      workspaceFolder,
+      FAKE_TELEMETRY,
+      () => {},
+      new Map(),
+    );
+
+    const startStub = sinon.stub(workspace, "start");
+    const restartSpy = sinon.spy(workspace, "restart");
+
+    await workspace.activate();
+
+    for (let i = 0; i < 5; i++) {
+      await new Promise((resolve) => setTimeout(resolve, 200));
+      fs.writeFileSync(path.join(gitDir, "rebase-apply"), "1");
+      await new Promise((resolve) => setTimeout(resolve, 200));
+      fs.rmSync(path.join(gitDir, "rebase-apply"));
+    }
+
+    // Give enough time for all watchers to fire and all debounces to run off
+    await new Promise((resolve) => setTimeout(resolve, 10000));
+
+    startStub.restore();
+    restartSpy.restore();
+
+    // The start call only happens once because of the inhibitRestart flag
+    assert.strictEqual(startStub.callCount, 1);
+    // The restart call only happens once because of the debounce
+    assert.strictEqual(restartSpy.callCount, 1);
+  }).timeout(60000);
+});
diff --git a/vscode/src/workspace.ts b/vscode/src/workspace.ts
index 98e6fc4db..d6a785541 100644
--- a/vscode/src/workspace.ts
+++ b/vscode/src/workspace.ts
@@ -417,12 +417,16 @@ export class Workspace implements WorkspaceInterface {
     const start = () => {
       this.#inhibitRestart = true;
     };
-    const stop = async () => {
-      this.#inhibitRestart = false;
+    const debouncedRestart = debounce(async () => {
       this.outputChannel.info(
         `Restarting the Ruby LSP because ${glob} changed`,
       );
       await this.restart();
+    }, 5000);
+
+    const stop = async () => {
+      this.#inhibitRestart = false;
+      await debouncedRestart();
     };
 
     this.context.subscriptions.push(