diff --git a/apps/webapp/app/routes/api.v1.artifacts.ts b/apps/webapp/app/routes/api.v1.artifacts.ts
index f0ff332812..82ae3f5375 100644
--- a/apps/webapp/app/routes/api.v1.artifacts.ts
+++ b/apps/webapp/app/routes/api.v1.artifacts.ts
@@ -52,9 +52,22 @@ export async function action({ request }: ActionFunctionArgs) {
         switch (error.type) {
           case "artifact_size_exceeds_limit": {
             logger.warn("Artifact size exceeds limit", { error });
+            const sizeMB = parseFloat((error.contentLength / (1024 * 1024)).toFixed(1));
+            const limitMB = parseFloat((error.sizeLimit / (1024 * 1024)).toFixed(1));
+
+            let errorMessage;
+
+            switch (body.data.type) {
+              case "deployment_context":
+                errorMessage = `Artifact size (${sizeMB} MB) exceeds the allowed limit of ${limitMB} MB. Make sure you are in the correct directory of your Trigger.dev project. Reach out to us if you are seeing this error consistently.`;
+                break;
+              default:
+                body.data.type satisfies never;
+                errorMessage = `Artifact size (${sizeMB} MB) exceeds the allowed limit of ${limitMB} MB`;
+            }
             return json(
               {
-                error: `Artifact size (${error.contentLength} bytes) exceeds the allowed limit of ${error.sizeLimit} bytes`,
+                error: errorMessage,
               },
               { status: 400 }
             );
diff --git a/apps/webapp/app/v3/services/deployment.server.ts b/apps/webapp/app/v3/services/deployment.server.ts
index ec9ea293af..11d659ab22 100644
--- a/apps/webapp/app/v3/services/deployment.server.ts
+++ b/apps/webapp/app/v3/services/deployment.server.ts
@@ -410,16 +410,16 @@ export class DeploymentService extends BaseService {
         })
       );
 
-    return getTokenFromCache()
-      .orElse(issueS2Token)
-      .andThen((token) =>
+    return getTokenFromCache().orElse(() =>
+      issueS2Token().andThen((token) =>
         cacheToken(token)
           .map(() => token)
           .orElse((error) => {
             logger.error("Failed to cache S2 token", { error });
             return okAsync(token); // ignore the cache error
           })
-      );
+      )
+    );
   }
 
   private getDeployment(projectId: string, friendlyId: string) {
diff --git a/packages/cli-v3/src/commands/deploy.ts b/packages/cli-v3/src/commands/deploy.ts
index 0a18e3ea70..d387c83d65 100644
--- a/packages/cli-v3/src/commands/deploy.ts
+++ b/packages/cli-v3/src/commands/deploy.ts
@@ -929,8 +929,9 @@ async function handleNativeBuildServerDeploy({
   });
 
   if (!artifactResult.success) {
-    $deploymentSpinner.stop("Failed to upload deployment files");
-    throw new Error(`Failed to create deployment artifact: ${artifactResult.error}`);
+    $deploymentSpinner.stop("Failed creating deployment artifact");
+    log.error(chalk.bold(chalkError(artifactResult.error)));
+    throw new OutroCommandError(`Deployment failed`);
   }
 
   const { artifactKey, uploadUrl, uploadFields } = artifactResult.data;
@@ -942,8 +943,9 @@ async function handleNativeBuildServerDeploy({
   const [readError, fileBuffer] = await tryCatch(readFile(archivePath));
 
   if (readError) {
-    $deploymentSpinner.stop("Failed to read deployment archive");
-    throw new Error(`Failed to read archive: ${readError.message}`);
+    $deploymentSpinner.stop("Failed reading deployment archive");
+    log.error(chalk.bold(chalkError(readError.message)));
+    throw new OutroCommandError(`Deployment failed`);
   }
 
   const formData = new FormData();
@@ -964,9 +966,14 @@ async function handleNativeBuildServerDeploy({
 
   if (uploadError || !uploadResponse?.ok) {
     $deploymentSpinner.stop("Failed to upload deployment files");
-    throw new Error(
-      `Failed to upload archive: ${uploadError?.message} ${uploadResponse?.status} ${uploadResponse?.statusText}`
+    log.error(
+      chalk.bold(
+        chalkError(
+          `${uploadError?.message} (${uploadResponse?.statusText} ${uploadResponse?.status})`
+        )
+      )
     );
+    throw new OutroCommandError(`Deployment failed`);
   }
 
   const [unlinkError] = await tryCatch(unlink(archivePath));