diff --git a/src/vs/platform/terminal/node/ptyService.ts b/src/vs/platform/terminal/node/ptyService.ts
index ddadd6a069d..5d6b474148c 100644
--- a/src/vs/platform/terminal/node/ptyService.ts
+++ b/src/vs/platform/terminal/node/ptyService.ts
@@ -210,10 +210,11 @@ export class PtyService extends Disposable implements IPtyService {
 
 	async attachToProcess(id: number): Promise<void> {
 		try {
-			this._throwIfNoPty(id).attach();
+			await this._throwIfNoPty(id).attach();
 			this._logService.trace(`Persistent process reconnection "${id}"`);
 		} catch (e) {
 			this._logService.trace(`Persistent process reconnection "${id}" failed`, e.message);
+			throw e;
 		}
 	}
 
@@ -543,8 +544,16 @@ export class PersistentTerminalProcess extends Disposable {
 		}));
 	}
 
-	attach(): void {
+	async attach(): Promise<void> {
 		this._logService.trace('persistentTerminalProcess#attach', this._persistentProcessId);
+		if (!this._disconnectRunner1.isScheduled() && !this._disconnectRunner2.isScheduled()) {
+			// Something wrong happened if the disconnect runner is not canceled, this likely means
+			// multiple windows attempted to attach.
+			if (!await this._isOrphaned()) {
+				throw new Error(`Cannot attach to persistent process "${this._persistentProcessId}", it is already adopted`);
+			}
+			this._logService.warn(`Persistent process "${this._persistentProcessId}": Process had no disconnect runners but was an orphan`);
+		}
 		this._disconnectRunner1.cancel();
 		this._disconnectRunner2.cancel();
 	}
diff --git a/src/vs/workbench/contrib/terminal/browser/terminalProcessManager.ts b/src/vs/workbench/contrib/terminal/browser/terminalProcessManager.ts
index bba89cdbcee..3e2725c70ff 100644
--- a/src/vs/workbench/contrib/terminal/browser/terminalProcessManager.ts
+++ b/src/vs/workbench/contrib/terminal/browser/terminalProcessManager.ts
@@ -210,7 +210,7 @@ export class TerminalProcessManager extends Disposable implements ITerminalProce
 		this._dimensions.rows = rows;
 		this._isScreenReaderModeEnabled = isScreenReaderModeEnabled;
 
-		let newProcess: ITerminalChildProcess;
+		let newProcess: ITerminalChildProcess | undefined;
 
 		if (shellLaunchConfig.customPtyImplementation) {
 			this._processType = ProcessType.PsuedoTerminal;
@@ -251,10 +251,12 @@ export class TerminalProcessManager extends Disposable implements ITerminalProce
 					if (result) {
 						newProcess = result;
 					} else {
-						this._logService.trace(`Attach to process failed for terminal ${shellLaunchConfig.attachPersistentProcess}`);
-						return undefined;
+						// Warn and just create a new terminal if attach failed for some reason
+						this._logService.warn(`Attach to process failed for terminal`, shellLaunchConfig.attachPersistentProcess);
+						shellLaunchConfig.attachPersistentProcess = undefined;
 					}
-				} else {
+				}
+				if (!newProcess) {
 					await this._terminalProfileResolverService.resolveShellLaunchConfig(shellLaunchConfig, {
 						remoteAuthority: this.remoteAuthority,
 						os: this.os
@@ -294,10 +296,12 @@ export class TerminalProcessManager extends Disposable implements ITerminalProce
 					if (result) {
 						newProcess = result;
 					} else {
-						this._logService.trace(`Attach to process failed for terminal ${shellLaunchConfig.attachPersistentProcess}`);
-						return undefined;
+						// Warn and just create a new terminal if attach failed for some reason
+						this._logService.warn(`Attach to process failed for terminal`, shellLaunchConfig.attachPersistentProcess);
+						shellLaunchConfig.attachPersistentProcess = undefined;
 					}
-				} else {
+				}
+				if (!newProcess) {
 					newProcess = await this._launchLocalProcess(backend, shellLaunchConfig, cols, rows, this.userHome, isScreenReaderModeEnabled, variableResolver);
 				}
 				if (!this._isDisposed) {
@@ -335,7 +339,7 @@ export class TerminalProcessManager extends Disposable implements ITerminalProce
 
 				if (this._preLaunchInputQueue.length > 0 && this._process) {
 					// Send any queued data that's waiting
-					newProcess.input(this._preLaunchInputQueue.join(''));
+					newProcess!.input(this._preLaunchInputQueue.join(''));
 					this._preLaunchInputQueue.length = 0;
 				}
 			}),