diff --git a/arduino-ide-extension/src/browser/boards/boards-service-provider.ts b/arduino-ide-extension/src/browser/boards/boards-service-provider.ts
index 65842eca3..279a2e3fa 100644
--- a/arduino-ide-extension/src/browser/boards/boards-service-provider.ts
+++ b/arduino-ide-extension/src/browser/boards/boards-service-provider.ts
@@ -158,15 +158,9 @@ export class BoardsServiceProvider
     this.lastAvailablePortsOnUpload = undefined;
   }
 
-  private portToAutoSelectCanBeDerived(): boolean {
-    return Boolean(
-      this.lastBoardsConfigOnUpload && this.lastAvailablePortsOnUpload
-    );
-  }
-
   attemptPostUploadAutoSelect(): void {
     setTimeout(() => {
-      if (this.portToAutoSelectCanBeDerived()) {
+      if (this.lastBoardsConfigOnUpload && this.lastAvailablePortsOnUpload) {
         this.attemptAutoSelect({
           ports: this._availablePorts,
           boards: this._availableBoards,
@@ -185,12 +179,12 @@ export class BoardsServiceProvider
   private deriveBoardConfigToAutoSelect(
     newState: AttachedBoardsChangeEvent['newState']
   ): void {
-    if (!this.portToAutoSelectCanBeDerived()) {
+    if (!this.lastBoardsConfigOnUpload || !this.lastAvailablePortsOnUpload) {
       this.boardConfigToAutoSelect = undefined;
       return;
     }
 
-    const oldPorts = this.lastAvailablePortsOnUpload!;
+    const oldPorts = this.lastAvailablePortsOnUpload;
     const { ports: newPorts, boards: newBoards } = newState;
 
     const appearedPorts =
@@ -205,20 +199,39 @@ export class BoardsServiceProvider
         Port.sameAs(board.port, port)
       );
 
-      const lastBoardsConfigOnUpload = this.lastBoardsConfigOnUpload!;
+      const lastBoardsConfigOnUpload = this.lastBoardsConfigOnUpload;
 
-      if (
-        boardOnAppearedPort &&
-        lastBoardsConfigOnUpload.selectedBoard &&
-        Board.sameAs(
+      if (boardOnAppearedPort && lastBoardsConfigOnUpload.selectedBoard) {
+        const boardIsSameHardware = Board.hardwareIdEquals(
           boardOnAppearedPort,
           lastBoardsConfigOnUpload.selectedBoard
-        )
-      ) {
+        );
+
+        const boardIsSameFqbn = Board.sameAs(
+          boardOnAppearedPort,
+          lastBoardsConfigOnUpload.selectedBoard
+        );
+
+        if (!boardIsSameHardware && !boardIsSameFqbn) continue;
+
+        let boardToAutoSelect = boardOnAppearedPort;
+        if (boardIsSameHardware && !boardIsSameFqbn) {
+          const { name, fqbn } = lastBoardsConfigOnUpload.selectedBoard;
+
+          boardToAutoSelect = {
+            ...boardToAutoSelect,
+            name:
+              boardToAutoSelect.name === Unknown || !boardToAutoSelect.name
+                ? name
+                : boardToAutoSelect.name,
+            fqbn: boardToAutoSelect.fqbn || fqbn,
+          };
+        }
+
         this.clearBoardDiscoverySnapshot();
 
         this.boardConfigToAutoSelect = {
-          selectedBoard: boardOnAppearedPort,
+          selectedBoard: boardToAutoSelect,
           selectedPort: port,
         };
         return;
@@ -326,8 +339,10 @@ export class BoardsServiceProvider
         // it is just a FQBN, so we need to find the `selected` board among the `AvailableBoards`
         const selectedAvailableBoard = AvailableBoard.is(selectedBoard)
           ? selectedBoard
-          : this._availableBoards.find((availableBoard) =>
-              Board.sameAs(availableBoard, selectedBoard)
+          : this._availableBoards.find(
+              (availableBoard) =>
+                Board.hardwareIdEquals(availableBoard, selectedBoard) ||
+                Board.sameAs(availableBoard, selectedBoard)
             );
         if (
           selectedAvailableBoard &&
@@ -353,9 +368,28 @@ export class BoardsServiceProvider
 
   protected tryReconnect(): boolean {
     if (this.latestValidBoardsConfig && !this.canUploadTo(this.boardsConfig)) {
+      // ** Reconnect to a board unplugged from, and plugged back into the same port
       for (const board of this.availableBoards.filter(
         ({ state }) => state !== AvailableBoard.State.incomplete
       )) {
+        if (
+          Board.hardwareIdEquals(
+            this.latestValidBoardsConfig.selectedBoard,
+            board
+          )
+        ) {
+          const { name, fqbn } = this.latestValidBoardsConfig.selectedBoard;
+          this.boardsConfig = {
+            selectedBoard: {
+              name: board.name === Unknown || !board.name ? name : board.name,
+              fqbn: board.fqbn || fqbn,
+              port: board.port,
+            },
+            selectedPort: board.port,
+          };
+          return true;
+        }
+
         if (
           this.latestValidBoardsConfig.selectedBoard.fqbn === board.fqbn &&
           this.latestValidBoardsConfig.selectedBoard.name === board.name &&
@@ -365,12 +399,15 @@ export class BoardsServiceProvider
           return true;
         }
       }
+      // **
 
+      // ** Reconnect to a board whose port changed due to an upload
       if (!this.boardConfigToAutoSelect) return false;
 
       this.boardsConfig = this.boardConfigToAutoSelect;
       this.boardConfigToAutoSelect = undefined;
       return true;
+      // **
     }
     return false;
   }
diff --git a/arduino-ide-extension/src/common/protocol/boards-service.ts b/arduino-ide-extension/src/common/protocol/boards-service.ts
index cbb057028..c955b9462 100644
--- a/arduino-ide-extension/src/common/protocol/boards-service.ts
+++ b/arduino-ide-extension/src/common/protocol/boards-service.ts
@@ -245,6 +245,7 @@ export interface Port {
   readonly protocol: string;
   readonly protocolLabel: string;
   readonly properties?: Record<string, string>;
+  readonly hardwareId?: string;
 }
 export namespace Port {
   export type Properties = Record<string, string>;
@@ -553,6 +554,19 @@ export namespace Board {
     return left.name === right.name && left.fqbn === right.fqbn;
   }
 
+  export function hardwareIdEquals(left: Board, right: Board): boolean {
+    if (left.port && right.port) {
+      const { hardwareId: leftHardwareId } = left.port;
+      const { hardwareId: rightHardwareId } = right.port;
+
+      if (leftHardwareId && rightHardwareId) {
+        return leftHardwareId === rightHardwareId;
+      }
+    }
+
+    return false;
+  }
+
   export function sameAs(left: Board, right: string | Board): boolean {
     // How to associate a selected board with one of the available cores: https://typefox.slack.com/archives/CJJHJCJSJ/p1571142327059200
     // 1. How to use the FQBN if any and infer the package ID from it: https://typefox.slack.com/archives/CJJHJCJSJ/p1571147549069100
diff --git a/arduino-ide-extension/src/node/board-discovery.ts b/arduino-ide-extension/src/node/board-discovery.ts
index bce8a36d0..8699b7232 100644
--- a/arduino-ide-extension/src/node/board-discovery.ts
+++ b/arduino-ide-extension/src/node/board-discovery.ts
@@ -323,14 +323,14 @@ export class BoardDiscovery
   }
 
   private fromRpcPort(rpcPort: RpcPort): Port {
-    const port = {
+    return {
       address: rpcPort.getAddress(),
       addressLabel: rpcPort.getLabel(),
       protocol: rpcPort.getProtocol(),
       protocolLabel: rpcPort.getProtocolLabel(),
       properties: Port.Properties.create(rpcPort.getPropertiesMap().toObject()),
+      hardwareId: rpcPort.getHardwareId(),
     };
-    return port;
   }
 }