diff --git a/src/api.ts b/src/api.ts
index 22de2618..063b7ae2 100644
--- a/src/api.ts
+++ b/src/api.ts
@@ -12,6 +12,7 @@ import * as vscode from "vscode";
 import * as ws from "ws";
 import { errToStr } from "./api-helper";
 import { CertificateError } from "./error";
+import { FeatureSet } from "./featureSet";
 import { getHeaderArgs } from "./headers";
 import { getProxyForUrl } from "./proxy";
 import { Storage } from "./storage";
@@ -174,6 +175,7 @@ export async function startWorkspaceIfStoppedOrFailed(
 	binPath: string,
 	workspace: Workspace,
 	writeEmitter: vscode.EventEmitter<string>,
+	featureSet: FeatureSet,
 ): Promise<Workspace> {
 	// Before we start a workspace, we make an initial request to check it's not already started
 	const updatedWorkspace = await restClient.getWorkspace(workspace.id);
@@ -191,6 +193,10 @@ export async function startWorkspaceIfStoppedOrFailed(
 			"--yes",
 			workspace.owner_name + "/" + workspace.name,
 		];
+		if (featureSet.buildReason) {
+			startArgs.push(...["--reason", "vscode_connection"]);
+		}
+
 		const startProcess = spawn(binPath, startArgs);
 
 		startProcess.stdout.on("data", (data: Buffer) => {
diff --git a/src/featureSet.ts b/src/featureSet.ts
index 958aeae5..67121229 100644
--- a/src/featureSet.ts
+++ b/src/featureSet.ts
@@ -4,6 +4,7 @@ export type FeatureSet = {
 	vscodessh: boolean;
 	proxyLogDirectory: boolean;
 	wildcardSSH: boolean;
+	buildReason: boolean;
 };
 
 /**
@@ -29,5 +30,10 @@ export function featureSetForVersion(
 		wildcardSSH:
 			(version ? version.compare("2.19.0") : -1) >= 0 ||
 			version?.prerelease[0] === "devel",
+
+		// The --reason flag was added to `coder start` in 2.25.0
+		buildReason:
+			(version?.compare("2.25.0") || 0) >= 0 ||
+			version?.prerelease[0] === "devel",
 	};
 }
diff --git a/src/remote.ts b/src/remote.ts
index 4a13ae56..59f04562 100644
--- a/src/remote.ts
+++ b/src/remote.ts
@@ -68,6 +68,7 @@ export class Remote {
 		workspace: Workspace,
 		label: string,
 		binPath: string,
+		featureSet: FeatureSet,
 	): Promise<Workspace | undefined> {
 		const workspaceName = `${workspace.owner_name}/${workspace.name}`;
 
@@ -140,6 +141,7 @@ export class Remote {
 									binPath,
 									workspace,
 									writeEmitter,
+									featureSet,
 								);
 								break;
 							case "failed":
@@ -159,6 +161,7 @@ export class Remote {
 										binPath,
 										workspace,
 										writeEmitter,
+										featureSet,
 									);
 									break;
 								}
@@ -393,6 +396,7 @@ export class Remote {
 				workspace,
 				parts.label,
 				binaryPath,
+				featureSet,
 			);
 			if (!updatedWorkspace) {
 				// User declined to start the workspace.