arduino
diff --git a/‎arduino-ide-extension/src/browser/contributions/upload-sketch.ts
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+25-2Lines changed: 25 additions & 2 deletions b/‎arduino-ide-extension/src/browser/contributions/upload-sketch.ts
Copy file name to clipboardExpand all lines: arduino-ide-extension/src/browser/contributions/upload-sketch.ts
+25-2Lines changed: 25 additions & 2 deletions
diff --git a/‎arduino-ide-extension/src/common/protocol/core-service.ts
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+5Lines changed: 5 additions & 0 deletions b/‎arduino-ide-extension/src/common/protocol/core-service.ts
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+5Lines changed: 5 additions & 0 deletions
diff --git a/‎arduino-ide-extension/src/node/core-service-impl.ts
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+14-1Lines changed: 14 additions & 1 deletion b/‎arduino-ide-extension/src/node/core-service-impl.ts
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+14-1Lines changed: 14 additions & 1 deletion
@@ -127,6 +127,7 @@ export class UploadSketch extends CoreServiceContribution {
         usingProgrammer,
         verifyOptions
       );
+
       if (!uploadOptions) {
         return;
       }
@@ -137,8 +138,30 @@ export class UploadSketch extends CoreServiceContribution {
 
       const uploadResponse = await this.doWithProgress({
         progressText: nls.localize('arduino/sketch/uploading', 'Uploading...'),
-        task: (progressId, coreService, token) =>
-          coreService.upload({ ...uploadOptions, progressId }, token),
+        task: async (progressId, coreService, token) => {
+          try {
+            const response = await coreService.upload(
+              { ...uploadOptions, progressId },
+              token
+            );
+            return response;
+          } catch (err) {
+            if (err.code === 4005) {
+              const uploadWithProgrammerOptions = await this.uploadOptions(
+                true,
+                verifyOptions
+              );
+              if (uploadWithProgrammerOptions) {
+                return await coreService.upload(
+                  { ...uploadWithProgrammerOptions, progressId },
+                  token
+                );
+              }
+            }
+
+            throw err;
+          }
+        },
         keepOutput: true,
         cancelable: true,
       });
 
@@ -71,13 +71,18 @@ export namespace CoreError {
     Upload: 4002,
     UploadUsingProgrammer: 4003,
     BurnBootloader: 4004,
+    UploadRequiresProgrammer: 4005,
   };
   export const VerifyFailed = declareCoreError(Codes.Verify);
   export const UploadFailed = declareCoreError(Codes.Upload);
   export const UploadUsingProgrammerFailed = declareCoreError(
     Codes.UploadUsingProgrammer
   );
   export const BurnBootloaderFailed = declareCoreError(Codes.BurnBootloader);
+  export const UploadRequiresProgrammer = declareCoreError(
+    Codes.UploadRequiresProgrammer
+  );
+
   export function is(
     error: unknown
   ): error is ApplicationError<number, ErrorLocation[]> {
 
@@ -1,4 +1,4 @@
-import type { ClientReadableStream } from '@grpc/grpc-js';
+import { type ClientReadableStream } from '@grpc/grpc-js';
 import { ApplicationError } from '@theia/core/lib/common/application-error';
 import type { CancellationToken } from '@theia/core/lib/common/cancellation';
 import { CommandService } from '@theia/core/lib/common/command';
@@ -41,6 +41,7 @@ import { Port as RpcPort } from './cli-protocol/cc/arduino/cli/commands/v1/port_
 import {
   BurnBootloaderRequest,
   BurnBootloaderResponse,
+  ProgrammerIsRequiredForUploadError,
   UploadRequest,
   UploadResponse,
   UploadUsingProgrammerRequest,
@@ -295,12 +296,24 @@ export class CoreServiceImpl extends CoreClientAware implements CoreService {
               reject(UserAbortApplicationError());
               return;
             }
+
+            if (
+              ServiceError.isInstanceOf(
+                error,
+                ProgrammerIsRequiredForUploadError
+              )
+            ) {
+              reject(CoreError.UploadRequiresProgrammer());
+              return;
+            }
+
             const message = nls.localize(
               'arduino/upload/error',
               '{0} error: {1}',
               firstToUpperCase(task),
               error.details
             );
+
             this.sendResponse(error.details, OutputMessage.Severity.Error);
             reject(
               errorCtor(