diff --git a/site/src/api/api.test.ts b/site/src/api/api.test.ts
index 5d3abc999d..99eb768384 100644
--- a/site/src/api/api.test.ts
+++ b/site/src/api/api.test.ts
@@ -1,4 +1,5 @@
 import {
+	MockProvisionerJob,
 	MockStoppedWorkspace,
 	MockTemplate,
 	MockTemplateVersion2,
@@ -275,6 +276,102 @@ describe("api.ts", () => {
 		});
 	});
 
+	describe("changeWorkspaceVersion", () => {
+		it("stops workspace before changing version if running", async () => {
+			vi.spyOn(API, "stopWorkspace").mockResolvedValueOnce({
+				...MockWorkspaceBuild,
+				transition: "stop",
+			});
+			vi.spyOn(API, "waitForBuild").mockResolvedValueOnce({
+				...MockProvisionerJob,
+				status: "succeeded",
+			});
+			vi.spyOn(API, "getWorkspaceBuildParameters").mockResolvedValueOnce([]);
+			vi.spyOn(API, "getTemplateVersionRichParameters").mockResolvedValueOnce(
+				[],
+			);
+			vi.spyOn(API, "postWorkspaceBuild").mockResolvedValueOnce({
+				...MockWorkspaceBuild,
+				template_version_id: MockTemplateVersion2.id,
+				transition: "start",
+			});
+
+			await API.changeWorkspaceVersion(MockWorkspace, MockTemplateVersion2.id);
+
+			expect(API.stopWorkspace).toHaveBeenCalledWith(MockWorkspace.id);
+			expect(API.postWorkspaceBuild).toHaveBeenCalledWith(MockWorkspace.id, {
+				transition: "start",
+				template_version_id: MockTemplateVersion2.id,
+				rich_parameter_values: [],
+			});
+		});
+
+		it("does not stop workspace if already stopped", async () => {
+			vi.spyOn(API, "stopWorkspace");
+			vi.spyOn(API, "getWorkspaceBuildParameters").mockResolvedValueOnce([]);
+			vi.spyOn(API, "getTemplateVersionRichParameters").mockResolvedValueOnce(
+				[],
+			);
+			vi.spyOn(API, "postWorkspaceBuild").mockResolvedValueOnce({
+				...MockWorkspaceBuild,
+				template_version_id: MockTemplateVersion2.id,
+				transition: "start",
+			});
+
+			await API.changeWorkspaceVersion(
+				MockStoppedWorkspace,
+				MockTemplateVersion2.id,
+			);
+
+			expect(API.stopWorkspace).not.toHaveBeenCalled();
+		});
+
+		it("rejects if stop is canceled", async () => {
+			vi.spyOn(API, "stopWorkspace").mockResolvedValueOnce({
+				...MockWorkspaceBuild,
+				transition: "stop",
+			});
+			vi.spyOn(API, "waitForBuild").mockResolvedValueOnce({
+				...MockProvisionerJob,
+				status: "canceled",
+			});
+			vi.spyOn(API, "getWorkspaceBuildParameters").mockResolvedValueOnce([]);
+			vi.spyOn(API, "getTemplateVersionRichParameters").mockResolvedValueOnce(
+				[],
+			);
+			vi.spyOn(API, "postWorkspaceBuild");
+
+			await expect(
+				API.changeWorkspaceVersion(MockWorkspace, MockTemplateVersion2.id),
+			).rejects.toThrow("Workspace stop was canceled");
+			expect(API.postWorkspaceBuild).not.toHaveBeenCalled();
+		});
+
+		it("throws MissingBuildParameters for missing params", async () => {
+			vi.spyOn(API, "getWorkspaceBuildParameters").mockResolvedValueOnce([]);
+			vi.spyOn(API, "getTemplateVersionRichParameters").mockResolvedValueOnce([
+				MockTemplateVersionParameter1,
+				{ ...MockTemplateVersionParameter2, mutable: false },
+			]);
+
+			let error = new Error();
+			try {
+				await API.changeWorkspaceVersion(
+					MockStoppedWorkspace,
+					MockTemplateVersion2.id,
+				);
+			} catch (e) {
+				error = e as Error;
+			}
+
+			expect(error).toBeInstanceOf(MissingBuildParameters);
+			expect((error as MissingBuildParameters).parameters).toEqual([
+				MockTemplateVersionParameter1,
+				{ ...MockTemplateVersionParameter2, mutable: false },
+			]);
+		});
+	});
+
 	describe("chat configuration endpoints", () => {
 		it.each<[string, () => Promise<unknown>, unknown]>([
 			[
diff --git a/site/src/api/api.ts b/site/src/api/api.ts
index 99d3e44e38..4fef6cbc16 100644
--- a/site/src/api/api.ts
+++ b/site/src/api/api.ts
@@ -2498,6 +2498,24 @@ class ApiMethods {
 		}));
 	};
 
+	/**
+	 * Stops a workspace if it is currently running and waits for the stop
+	 * to complete. Throws if the stop build is canceled.
+	 */
+	private stopWorkspaceIfRunning = async (
+		workspace: TypesGen.Workspace,
+	): Promise<void> => {
+		// Workspace is already in a state where it's "stopped".
+		if (workspace.latest_build.status !== "running") return;
+
+		const stopBuild = await this.stopWorkspace(workspace.id);
+		const awaitedStopBuild = await this.waitForBuild(stopBuild);
+
+		if (awaitedStopBuild?.status === "canceled") {
+			throw new Error("Workspace stop was canceled.");
+		}
+	};
+
 	/** Steps to change the workspace version
 	 * - Get the latest template to access the latest active version
 	 * - Get the current build parameters
@@ -2505,6 +2523,7 @@ class ApiMethods {
 	 * - Update the build parameters and check if there are missed parameters for
 	 *   the new version
 	 *   - If there are missing parameters raise an error
+	 * - Stop the workspace if it is already running
 	 * - Create a build with the version and updated build parameters
 	 */
 	changeWorkspaceVersion = async (
@@ -2539,6 +2558,8 @@ class ApiMethods {
 			throw new MissingBuildParameters(missingParameters, templateVersionId);
 		}
 
+		await this.stopWorkspaceIfRunning(workspace);
+
 		return this.postWorkspaceBuild(workspace.id, {
 			transition: "start",
 			template_version_id: templateVersionId,
@@ -2553,7 +2574,7 @@ class ApiMethods {
 	 * - Update the build parameters and check if there are missed parameters for
 	 *   the newest version
 	 *   - If there are missing parameters raise an error
-	 * - Stop the workspace with the current template version if it is already running
+	 * - Stop the workspace if it is already running
 	 * - Create a build with the latest version and updated build parameters
 	 */
 	updateWorkspace = async (
@@ -2585,18 +2606,7 @@ class ApiMethods {
 			}
 		}
 
-		// Stop the workspace if it is already running.
-		if (workspace.latest_build.status === "running") {
-			const stopBuild = await this.stopWorkspace(workspace.id);
-			const awaitedStopBuild = await this.waitForBuild(stopBuild);
-			// If the stop is canceled halfway through, we bail.
-			// This is the same behaviour as restartWorkspace.
-			if (awaitedStopBuild?.status === "canceled") {
-				return Promise.reject(
-					new Error("Workspace stop was canceled, not proceeding with update."),
-				);
-			}
-		}
+		await this.stopWorkspaceIfRunning(workspace);
 
 		try {
 			return await this.postWorkspaceBuild(workspace.id, {