diff --git a/cli/metadata.ts b/cli/metadata.ts
index d547cee29f..1591bedba6 100644
--- a/cli/metadata.ts
+++ b/cli/metadata.ts
@@ -49,6 +49,13 @@ import { FlowFile, replaceInlineScripts } from "./flow.ts";
 import { getIsWin } from "./main.ts";
 import { FlowValue } from "./gen/types.gen.ts";
 
+export class LockfileGenerationError extends Error {
+  constructor(message: string) {
+    super(message);
+    this.name = 'LockfileGenerationError';
+  }
+}
+
 export async function generateAllMetadata() { }
 
 function findClosestRawReqs(
@@ -376,9 +383,16 @@ async function updateScriptLock(
     const response = JSON.parse(responseText);
     const lock = response.lock;
     if (lock === undefined) {
-      throw new Error(
-        `Failed to generate lockfile. Full response was: ${JSON.stringify(
-          response
+      if (response?.["error"]?.["message"]) {
+        throw new LockfileGenerationError(
+          `Failed to generate lockfile: ${response?.["error"]?.["message"]}`
+        );
+      }
+      throw new LockfileGenerationError(
+        `Failed to generate lockfile: ${JSON.stringify(
+          response,
+          null,
+          2
         )}`
       );
     }
@@ -395,8 +409,11 @@ async function updateScriptLock(
       metadataContent.lock = "";
     }
   } catch (e) {
-    throw new Error(
-      `Failed to generate lockfile. Status was: ${rawResponse.statusText}, ${responseText}, ${e}`
+    if (e instanceof LockfileGenerationError) {
+      throw e;
+    }
+    throw new LockfileGenerationError(
+      `Failed to generate lockfile:${rawResponse.statusText}, ${responseText}, ${e}`
     );
   }
 }
diff --git a/cli/script.ts b/cli/script.ts
index 6ab67212e8..37ae635380 100644
--- a/cli/script.ts
+++ b/cli/script.ts
@@ -990,7 +990,7 @@ const command = new Command()
   .action(bootstrap as any)
   .command(
     "generate-metadata",
-    "re-generate the metadata file updating the lock and the script schema (for flows, use `wmill flow generate - locks`)"
+    "re-generate the metadata file updating the lock and the script schema (for flows, use `wmill flow generate-locks`)"
   )
   .arguments("[script:file]")
   .option("--yes", "Skip confirmation prompt")