diff --git a/src/arduino/arduino.ts b/src/arduino/arduino.ts
index 73619a7b..865032d9 100644
--- a/src/arduino/arduino.ts
+++ b/src/arduino/arduino.ts
@@ -24,6 +24,12 @@ import { SerialMonitor } from "../serialmonitor/serialMonitor";
 import { UsbDetector } from "../serialmonitor/usbDetector";
 import { ProgrammerManager } from "./programmerManager";
 
+export enum BuildMode {
+    Verify = "Verify",
+    Upload = "Upload",
+    UploadUsingProgrammer = "Upload (w/programmer)",
+};
+
 /**
  * Represent an Arduino application based on the official Arduino IDE.
  */
@@ -93,7 +99,7 @@ export class ArduinoApp {
         }
     }
 
-    public async upload() {
+    public async buildSketch(mode: BuildMode, output: string = "") {
         const dc = DeviceContext.getInstance();
         const boardDescriptor = this.getBoardBuildString();
         if (!boardDescriptor) {
@@ -109,7 +115,7 @@ export class ArduinoApp {
             await this.getMainSketch(dc);
         }
 
-        if ((!dc.configuration || !/upload_method=[^=,]*st[^,]*link/i.test(dc.configuration)) && !dc.port) {
+        if (this.configRequiresSerialForUpload(mode) && !dc.port) {
             const choice = await vscode.window.showInformationMessage(
                 "Serial port is not specified. Do you want to select a serial port for uploading?",
                 "Yes", "No");
@@ -120,12 +126,10 @@ export class ArduinoApp {
         }
 
         arduinoChannel.show();
-        arduinoChannel.start(`Upload sketch - ${dc.sketch}`);
+        arduinoChannel.start(`${mode} sketch - ${dc.sketch}`);
 
         const serialMonitor = SerialMonitor.getInstance();
 
-        const needRestore = await serialMonitor.closeSerialMonitor(dc.port);
-        UsbDetector.getInstance().pauseListening();
         await vscode.workspace.saveAll(false);
 
         if (dc.prebuild) {
@@ -141,146 +145,35 @@ export class ArduinoApp {
         }
 
         const appPath = path.join(ArduinoWorkspace.rootPath, dc.sketch);
-        const args = ["--upload", "--board", boardDescriptor];
-        if (dc.port) {
-            args.push("--port", dc.port);
-        }
-        args.push(appPath);
-        if (VscodeSettings.getInstance().logLevel === "verbose") {
-            args.push("--verbose");
-        }
-        if (dc.output) {
-            const outputPath = path.resolve(ArduinoWorkspace.rootPath, dc.output);
-            const dirPath = path.dirname(outputPath);
-            if (!util.directoryExistsSync(dirPath)) {
-                Logger.notifyUserError("InvalidOutPutPath", new Error(constants.messages.INVALID_OUTPUT_PATH + outputPath));
-                return;
-            }
 
-            args.push("--pref", `build.path=${outputPath}`);
-            arduinoChannel.info(`Please see the build logs in Output path: ${outputPath}`);
+        const args = [];
+        if (mode === BuildMode.Verify) {
+            args.push("--verify");
         } else {
-            const msg = "Output path is not specified. Unable to reuse previously compiled files. Upload could be slow. See README.";
-            arduinoChannel.warning(msg);
-        }
-        await util.spawn(this._settings.commandPath, arduinoChannel.channel, args).then(async () => {
-            UsbDetector.getInstance().resumeListening();
-            if (needRestore) {
-                await serialMonitor.openSerialMonitor();
-            }
-            arduinoChannel.end(`Uploaded the sketch: ${dc.sketch}${os.EOL}`);
-        }, (reason) => {
-            arduinoChannel.error(`Exit with code=${reason.code}${os.EOL}`);
-        });
-    }
-
-    public async uploadUsingProgrammer() {
-        const dc = DeviceContext.getInstance();
-        const boardDescriptor = this.getBoardBuildString();
-        if (!boardDescriptor) {
-            return;
-        }
-
-        const selectProgrammer = this.getProgrammerString();
-        if (!selectProgrammer) {
-            return;
-        }
+            args.push("--upload");
 
-        if (!ArduinoWorkspace.rootPath) {
-            vscode.window.showWarningMessage("Cannot find the sketch file.");
-            return;
-        }
-
-        if (!dc.sketch || !util.fileExistsSync(path.join(ArduinoWorkspace.rootPath, dc.sketch))) {
-            await this.getMainSketch(dc);
-        }
-        if (!dc.port) {
-            const choice = await vscode.window.showInformationMessage(
-                "Serial port is not specified. Do you want to select a serial port for uploading?",
-                "Yes", "No");
-            if (choice === "Yes") {
-                vscode.commands.executeCommand("arduino.selectSerialPort");
+            if (dc.port) {
+                args.push("--port", dc.port);
             }
-            return;
-        }
-
-        arduinoChannel.show();
-        arduinoChannel.start(`Upload sketch - ${dc.sketch}`);
-
-        const serialMonitor = SerialMonitor.getInstance();
-
-        const needRestore = await serialMonitor.closeSerialMonitor(dc.port);
-        UsbDetector.getInstance().pauseListening();
-        await vscode.workspace.saveAll(false);
 
-        const appPath = path.join(ArduinoWorkspace.rootPath, dc.sketch);
-        const args = ["--upload", "--board", boardDescriptor, "--port", dc.port, "--useprogrammer",
-            "--pref", "programmer=" + selectProgrammer, appPath];
-        if (VscodeSettings.getInstance().logLevel === "verbose") {
-            args.push("--verbose");
-        }
-        if (dc.output) {
-            const outputPath = path.resolve(ArduinoWorkspace.rootPath, dc.output);
-            const dirPath = path.dirname(outputPath);
-            if (!util.directoryExistsSync(dirPath)) {
-                Logger.notifyUserError("InvalidOutPutPath", new Error(constants.messages.INVALID_OUTPUT_PATH + outputPath));
-                return;
-            }
+            if (mode === BuildMode.UploadUsingProgrammer) {
+                const programmer = this.getProgrammerString();
+                if (!programmer) {
+                    return;
+                }
 
-            args.push("--pref", `build.path=${outputPath}`);
-            arduinoChannel.info(`Please see the build logs in Output path: ${outputPath}`);
-        } else {
-            const msg = "Output path is not specified. Unable to reuse previously compiled files. Upload could be slow. See README.";
-            arduinoChannel.warning(msg);
-        }
-        await util.spawn(this._settings.commandPath, arduinoChannel.channel, args).then(async () => {
-            UsbDetector.getInstance().resumeListening();
-            if (needRestore) {
-                await serialMonitor.openSerialMonitor();
+                args.push("--useprogrammer", "--pref", "programmer=" + programmer);
             }
-            arduinoChannel.end(`Uploaded the sketch: ${dc.sketch}${os.EOL}`);
-        }, (reason) => {
-            arduinoChannel.error(`Exit with code=${reason.code}${os.EOL}`);
-        });
-    }
-
-    public async verify(output: string = "") {
-        const dc = DeviceContext.getInstance();
-        const boardDescriptor = this.getBoardBuildString();
-        if (!boardDescriptor) {
-            return;
-        }
-
-        if (!ArduinoWorkspace.rootPath) {
-            vscode.window.showWarningMessage("Cannot find the sketch file.");
-            return;
-        }
-
-        if (!dc.sketch || !util.fileExistsSync(path.join(ArduinoWorkspace.rootPath, dc.sketch))) {
-            await this.getMainSketch(dc);
         }
 
-        await vscode.workspace.saveAll(false);
+        args.push("--board", boardDescriptor)
 
-        arduinoChannel.start(`Verify sketch - ${dc.sketch}`);
-
-        if (dc.prebuild) {
-            arduinoChannel.info(`Run prebuild command: ${dc.prebuild}`);
-            const prebuildargs = dc.prebuild.split(" ");
-            const prebuildCommand = prebuildargs.shift();
-            try {
-                await util.spawn(prebuildCommand, arduinoChannel.channel, prebuildargs, { shell: true, cwd: ArduinoWorkspace.rootPath });
-            } catch (ex) {
-                arduinoChannel.error(`Run prebuild failed: \n${ex.error}`);
-                return;
-            }
-        }
+        args.push(appPath);
 
-        const appPath = path.join(ArduinoWorkspace.rootPath, dc.sketch);
-        const args = ["--verify", "--board", boardDescriptor, appPath];
         if (VscodeSettings.getInstance().logLevel === "verbose") {
             args.push("--verbose");
         }
+
         if (output || dc.output) {
             const outputPath = path.resolve(ArduinoWorkspace.rootPath, output || dc.output);
             const dirPath = path.dirname(outputPath);
@@ -290,28 +183,37 @@ export class ArduinoApp {
             }
 
             args.push("--pref", `build.path=${outputPath}`);
+
             arduinoChannel.info(`Please see the build logs in Output path: ${outputPath}`);
         } else {
-            const msg = "Output path is not specified. Unable to reuse previously compiled files. Verify could be slow. See README.";
+            const msg = `Output path is not specified. Unable to reuse previously compiled files. ${mode} could be slow. See README.`;
             arduinoChannel.warning(msg);
         }
-
-        arduinoChannel.show();
-        // we need to return the result of verify
+        // we need to return the result of the process
+        let restoreSerial: boolean = false;
         try {
+            if (mode !== BuildMode.Verify) {
+                restoreSerial = await serialMonitor.closeSerialMonitor(dc.port);
+                UsbDetector.getInstance().pauseListening();
+            }
+
             await util.spawn(this._settings.commandPath, arduinoChannel.channel, args);
-            arduinoChannel.end(`Finished verify sketch - ${dc.sketch}${os.EOL}`);
+            arduinoChannel.end(`${mode} finished - ${dc.sketch}${os.EOL}`);
             return true;
         } catch (reason) {
             const msg = reason.code ?
                 `Exit with code=${reason.code}${os.EOL}` :
-                reason.message ?
-                    reason.message :
-                    JSON.stringify(reason);
+                reason.message ? reason.message : JSON.stringify(reason);
             arduinoChannel.error(msg);
             return false;
+        } finally {
+            if (mode !== BuildMode.Verify) {
+                UsbDetector.getInstance().resumeListening();
+                if (restoreSerial) {
+                    await serialMonitor.openSerialMonitor();
+                }
+            }
         }
-
     }
 
     public tryToUpdateIncludePaths() {
@@ -760,4 +662,20 @@ Please make sure the folder is not occupied by other procedures .`);
             throw new Error("No sketch file was found.");
         }
     }
+
+    private configRequiresSerialForUpload(mode: BuildMode): boolean {
+        const dc = DeviceContext.getInstance();
+
+        if (mode === BuildMode.Verify) {
+            return false;
+        } else if (mode === BuildMode.UploadUsingProgrammer) {
+            // Currently all programmer configurations require a selected serial port
+            return true;
+        }
+
+        // Certain boards allow configuration of the STLink programmers as part of the board
+        // config and use during the regular upload, rather than "Upload using programmer"
+        // https://github.com/microsoft/vscode-arduino/issues/595
+        return (!dc.configuration || !/upload_method=[^=,]*st[^,]*link/i.test(dc.configuration));
+    }
 }
diff --git a/src/debug/configurationProvider.ts b/src/debug/configurationProvider.ts
index c08546f2..614dc542 100644
--- a/src/debug/configurationProvider.ts
+++ b/src/debug/configurationProvider.ts
@@ -4,7 +4,7 @@
 import * as path from "path";
 import * as vscode from "vscode";
 
-import { ArduinoApp } from "../arduino/arduino";
+import { BuildMode } from "../arduino/arduino";
 import ArduinoActivator from "../arduinoActivator";
 import ArduinoContext from "../arduinoContext";
 
@@ -136,7 +136,7 @@ export class ArduinoDebugConfigurationProvider implements vscode.DebugConfigurat
             config.program = path.join(ArduinoWorkspace.rootPath, outputFolder, `${path.basename(dc.sketch)}.elf`);
 
             // always compile elf to make sure debug the right elf
-            if (!await ArduinoContext.arduinoApp.verify(outputFolder)) {
+            if (!await ArduinoContext.arduinoApp.buildSketch(BuildMode.Verify, outputFolder)) {
                 vscode.window.showErrorMessage("Failure to verify the program, please check output for details.");
                 return false;
             }
diff --git a/src/extension.ts b/src/extension.ts
index c4112bd7..e999abae 100644
--- a/src/extension.ts
+++ b/src/extension.ts
@@ -27,6 +27,7 @@ const completionProviderModule = impor("./langService/completionProvider") as ty
 import * as Logger from "./logger/logger";
 const nsatModule =
     impor("./nsat") as typeof import ("./nsat");
+import { BuildMode } from "./arduino/arduino";
 import { SerialMonitor } from "./serialmonitor/serialMonitor";
 const usbDetectorModule = impor("./serialmonitor/usbDetector") as typeof import ("./serialmonitor/usbDetector");
 
@@ -121,7 +122,7 @@ export async function activate(context: vscode.ExtensionContext) {
                     location: vscode.ProgressLocation.Window,
                     title: "Arduino: Verifying...",
                 }, async () => {
-                    await arduinoContextModule.default.arduinoApp.verify();
+                    await arduinoContextModule.default.arduinoApp.buildSketch(BuildMode.Verify);
                 });
             } catch (ex) {
             }
@@ -142,7 +143,7 @@ export async function activate(context: vscode.ExtensionContext) {
                     location: vscode.ProgressLocation.Window,
                     title: "Arduino: Uploading...",
                 }, async () => {
-                    await arduinoContextModule.default.arduinoApp.upload();
+                    await arduinoContextModule.default.arduinoApp.buildSketch(BuildMode.Upload);
                 });
             } catch (ex) {
             }
@@ -177,7 +178,7 @@ export async function activate(context: vscode.ExtensionContext) {
         if (!status.compile) {
             status.compile = "upload";
             try {
-                await arduinoContextModule.default.arduinoApp.uploadUsingProgrammer();
+                await arduinoContextModule.default.arduinoApp.buildSketch(BuildMode.UploadUsingProgrammer);
             } catch (ex) {
             }
             delete status.compile;