diff --git a/packages/wrangler/e2e/versions.test.ts b/packages/wrangler/e2e/versions.test.ts
index d065d5a54bb9..8d0eef3e5358 100644
--- a/packages/wrangler/e2e/versions.test.ts
+++ b/packages/wrangler/e2e/versions.test.ts
@@ -546,7 +546,7 @@ describe("versions deploy", { timeout: TIMEOUT }, () => {
 		);
 
 		expect(normalize(upload.output)).toMatchInlineSnapshot(`
-			"X [ERROR] Legacy Assets are not supported in Gradual Deployments.
+			"X [ERROR] Legacy Assets does not support uploading versions through \`wrangler versions upload\`. You must use \`wrangler deploy\` instead.
 			🪵  Logs were written to "<LOG>""
 		`);
 	});
@@ -580,7 +580,7 @@ describe("versions deploy", { timeout: TIMEOUT }, () => {
 		const upload = await helper.run(`wrangler versions upload  --x-versions`);
 
 		expect(normalize(upload.output)).toMatchInlineSnapshot(`
-			"X [ERROR] Workers Sites are not supported in Gradual Deployments.
+			"X [ERROR] Workers Sites does not support uploading versions through \`wrangler versions upload\`. You must use \`wrangler deploy\` instead.
 			🪵  Logs were written to "<LOG>""
 		`);
 	});
diff --git a/packages/wrangler/src/versions/index.ts b/packages/wrangler/src/versions/index.ts
index 0d52d2bc5e9a..a541b3a13bc6 100644
--- a/packages/wrangler/src/versions/index.ts
+++ b/packages/wrangler/src/versions/index.ts
@@ -219,12 +219,12 @@ export async function versionsUploadHandler(
 
 	if (args.site || config.site) {
 		throw new UserError(
-			"Workers Sites are not supported in Gradual Deployments."
+			"Workers Sites does not support uploading versions through `wrangler versions upload`. You must use `wrangler deploy` instead."
 		);
 	}
 	if (args.legacyAssets || config.legacy_assets) {
 		throw new UserError(
-			"Legacy Assets are not supported in Gradual Deployments."
+			"Legacy Assets does not support uploading versions through `wrangler versions upload`. You must use `wrangler deploy` instead."
 		);
 	}
 
diff --git a/packages/wrangler/src/versions/secrets/index.ts b/packages/wrangler/src/versions/secrets/index.ts
index a4266c08ce49..206af9ca8da8 100644
--- a/packages/wrangler/src/versions/secrets/index.ts
+++ b/packages/wrangler/src/versions/secrets/index.ts
@@ -254,7 +254,7 @@ async function parseModules(
 		// Workers Sites is not supported
 		if (formData.get("__STATIC_CONTENT_MANIFEST") !== null) {
 			throw new UserError(
-				"Workers Sites is not supported for `versions secret put` today."
+				"Workers Sites and Legacy Assets do not support updating secrets through `wrangler versions secret put`. You must use `wrangler secret put` instead."
 			);
 		}