diff --git a/src/commands.ts b/src/commands.ts
index cff624105..e55283c2b 100644
--- a/src/commands.ts
+++ b/src/commands.ts
@@ -98,6 +98,7 @@ export enum Commands {
     COVER_ALL_TESTS = "swift.coverAllTests",
     OPEN_MANIFEST = "swift.openManifest",
     RESTART_LSP = "swift.restartLSPServer",
+    SELECT_TOOLCHAIN = "swift.selectToolchain",
 }
 
 /**
diff --git a/src/toolchain/SelectedXcodeWatcher.ts b/src/toolchain/SelectedXcodeWatcher.ts
index d7954e810..5d06c4c05 100644
--- a/src/toolchain/SelectedXcodeWatcher.ts
+++ b/src/toolchain/SelectedXcodeWatcher.ts
@@ -17,6 +17,7 @@ import * as vscode from "vscode";
 import { SwiftOutputChannel } from "../ui/SwiftOutputChannel";
 import { showReloadExtensionNotification } from "../ui/ReloadExtension";
 import configuration from "../configuration";
+import { removeToolchainPath, selectToolchain } from "../ui/ToolchainSelection";
 
 export class SelectedXcodeWatcher implements vscode.Disposable {
     private xcodePath: string | undefined;
@@ -66,20 +67,40 @@ export class SelectedXcodeWatcher implements vscode.Disposable {
      */
     private async setup() {
         this.xcodePath = await this.xcodeSymlink();
+        if (
+            this.xcodePath &&
+            configuration.path &&
+            !configuration.path.startsWith(this.xcodePath)
+        ) {
+            this.xcodePath = undefined; // Notify user when initially launching that xcode changed since last session
+        }
         this.interval = setInterval(async () => {
             if (this.disposed) {
                 return clearInterval(this.interval);
             }
 
             const newXcodePath = await this.xcodeSymlink();
-            if (!configuration.path && newXcodePath && this.xcodePath !== newXcodePath) {
+            if (newXcodePath && this.xcodePath !== newXcodePath) {
                 this.outputChannel.appendLine(
                     `Selected Xcode changed from ${this.xcodePath} to ${newXcodePath}`
                 );
                 this.xcodePath = newXcodePath;
-                await showReloadExtensionNotification(
-                    "The Swift Extension has detected a change in the selected Xcode. Please reload the extension to apply the changes."
-                );
+                if (!configuration.path) {
+                    await showReloadExtensionNotification(
+                        "The Swift Extension has detected a change in the selected Xcode. Please reload the extension to apply the changes."
+                    );
+                } else {
+                    const selected = await vscode.window.showWarningMessage(
+                        'The Swift Extension has detected a change in the selected Xcode which does not match the value of your "swift.path" setting. Would you like to update your configured "swift.path" setting?',
+                        "Remove From Settings",
+                        "Select Toolchain"
+                    );
+                    if (selected === "Remove From Settings") {
+                        await removeToolchainPath();
+                    } else if (selected === "Select Toolchain") {
+                        await selectToolchain();
+                    }
+                }
             }
         }, this.checkIntervalMs);
     }
diff --git a/src/ui/ToolchainSelection.ts b/src/ui/ToolchainSelection.ts
index 622f2042c..202ba8785 100644
--- a/src/ui/ToolchainSelection.ts
+++ b/src/ui/ToolchainSelection.ts
@@ -17,6 +17,7 @@ import * as path from "path";
 import { showReloadExtensionNotification } from "./ReloadExtension";
 import { SwiftToolchain } from "../toolchain/toolchain";
 import configuration from "../configuration";
+import { Commands } from "../commands";
 
 /**
  * Open the installation page on Swift.org
@@ -28,7 +29,7 @@ export async function downloadToolchain() {
             "Select Toolchain"
         );
         if (selected === "Select Toolchain") {
-            await vscode.commands.executeCommand("swift.selectToolchain");
+            await selectToolchain();
         }
     }
 }
@@ -43,7 +44,7 @@ export async function installSwiftly() {
             "Select Toolchain"
         );
         if (selected === "Select Toolchain") {
-            await vscode.commands.executeCommand("swift.selectToolchain");
+            await selectToolchain();
         }
     }
 }
@@ -87,10 +88,14 @@ export async function showToolchainError(): Promise<void> {
     if (selected === "Remove From Settings") {
         await removeToolchainPath();
     } else if (selected === "Select Toolchain") {
-        await vscode.commands.executeCommand("swift.selectToolchain");
+        await selectToolchain();
     }
 }
 
+export async function selectToolchain() {
+    await vscode.commands.executeCommand(Commands.SELECT_TOOLCHAIN);
+}
+
 /** A {@link vscode.QuickPickItem} that contains the path to an installed Swift toolchain */
 type SwiftToolchainItem = PublicSwiftToolchainItem | XcodeToolchainItem;
 
@@ -351,7 +356,7 @@ async function showDeveloperDirQuickPick(xcodePaths: string[]): Promise<string |
 /**
  * Delete all set Swift path settings.
  */
-async function removeToolchainPath() {
+export async function removeToolchainPath() {
     const swiftSettings = vscode.workspace.getConfiguration("swift");
     const swiftEnvironmentSettings = swiftSettings.inspect("swiftEnvironmentVariables");
     if (swiftEnvironmentSettings?.globalValue) {
diff --git a/test/unit-tests/toolchain/SelectedXcodeWatcher.test.ts b/test/unit-tests/toolchain/SelectedXcodeWatcher.test.ts
index 490bca449..8b9022eb1 100644
--- a/test/unit-tests/toolchain/SelectedXcodeWatcher.test.ts
+++ b/test/unit-tests/toolchain/SelectedXcodeWatcher.test.ts
@@ -25,11 +25,15 @@ import {
     mockObject,
 } from "../../MockUtils";
 import configuration from "../../../src/configuration";
+import { Commands } from "../../../src/commands";
 
 suite("Selected Xcode Watcher", () => {
     const mockedVSCodeWindow = mockGlobalObject(vscode, "window");
     let mockOutputChannel: MockedObject<SwiftOutputChannel>;
     const pathConfig = mockGlobalValue(configuration, "path");
+    const mockWorkspace = mockGlobalObject(vscode, "workspace");
+    const mockCommands = mockGlobalObject(vscode, "commands");
+    let mockSwiftConfig: MockedObject<vscode.WorkspaceConfiguration>;
 
     setup(function () {
         // Xcode only exists on macOS, so the SelectedXcodeWatcher is macOS-only.
@@ -42,6 +46,12 @@ suite("Selected Xcode Watcher", () => {
         });
 
         pathConfig.setValue("");
+
+        mockSwiftConfig = mockObject<vscode.WorkspaceConfiguration>({
+            inspect: mockFn(),
+            update: mockFn(),
+        });
+        mockWorkspace.getConfiguration.returns(instance(mockSwiftConfig));
     });
 
     async function run(symLinksOnCallback: (string | undefined)[]) {
@@ -84,11 +94,50 @@ suite("Selected Xcode Watcher", () => {
         );
     });
 
-    test("Ignores when path is explicitly set", async () => {
+    test("Warns that setting is out of date", async () => {
         pathConfig.setValue("/path/to/swift/bin");
 
-        await run(["/foo", "/bar"]);
+        await run(["/path/to/swift/bin", "/foo", "/foo"]);
 
-        expect(mockedVSCodeWindow.showWarningMessage).to.have.not.been.called;
+        expect(mockedVSCodeWindow.showWarningMessage).to.have.been.calledOnceWithExactly(
+            'The Swift Extension has detected a change in the selected Xcode which does not match the value of your "swift.path" setting. Would you like to update your configured "swift.path" setting?',
+            "Remove From Settings",
+            "Select Toolchain"
+        );
+    });
+
+    test("Warns that setting is out of date on startup", async () => {
+        pathConfig.setValue("/path/to/swift/bin");
+
+        await run(["/foo", "/foo"]);
+
+        expect(mockedVSCodeWindow.showWarningMessage).to.have.been.calledOnceWithExactly(
+            'The Swift Extension has detected a change in the selected Xcode which does not match the value of your "swift.path" setting. Would you like to update your configured "swift.path" setting?',
+            "Remove From Settings",
+            "Select Toolchain"
+        );
+    });
+
+    test("Remove setting", async () => {
+        pathConfig.setValue("/path/to/swift/bin");
+
+        mockedVSCodeWindow.showWarningMessage.resolves("Remove From Settings" as any);
+
+        await run(["/foo", "/foo"]);
+
+        expect(mockSwiftConfig.update.args).to.deep.equal([
+            ["path", undefined, vscode.ConfigurationTarget.Global],
+            ["path", undefined, vscode.ConfigurationTarget.Workspace],
+        ]);
+    });
+
+    test("Select toolchain", async () => {
+        pathConfig.setValue("/path/to/swift/bin");
+
+        mockedVSCodeWindow.showWarningMessage.resolves("Select Toolchain" as any);
+
+        await run(["/foo", "/foo"]);
+
+        expect(mockCommands.executeCommand).to.have.been.calledOnceWith(Commands.SELECT_TOOLCHAIN);
     });
 });