diff --git a/src/windowsPtyAgent.test.ts b/src/windowsPtyAgent.test.ts
index 3a80d64b8..a4a065768 100644
--- a/src/windowsPtyAgent.test.ts
+++ b/src/windowsPtyAgent.test.ts
@@ -64,10 +64,10 @@ if (process.platform === 'win32') {
         check('asdf', ['quotes "in the" middle'], 'asdf "quotes \\"in the\\" middle"');
       });
       it('array argument quotes near start', () => {
-        check('asdf', ['"quotes" near start'], 'asdf \\"quotes\\" near start');
+        check('asdf', ['"quotes" near start'], 'asdf "\\"quotes\\" near start"');
       });
       it('array argument quotes near end', () => {
-        check('asdf', ['quotes "near end"'], 'asdf quotes \\"near end\\"');
+        check('asdf', ['quotes "near end"'], 'asdf "quotes \\"near end\\""');
       });
     });
 
diff --git a/src/windowsPtyAgent.ts b/src/windowsPtyAgent.ts
index a94454860..2db771357 100644
--- a/src/windowsPtyAgent.ts
+++ b/src/windowsPtyAgent.ts
@@ -129,13 +129,14 @@ export function argsToCommandLine(file: string, args: ArgvOrCommandLine): string
     }
     const arg = argv[argIndex];
     // if it is empty or it contains whitespace and is not already quoted
+    const hasLopsidedEnclosingQuote = xOr((arg[0] !== '"'), (arg[arg.length - 1] !== '"'));
+    const hasNoEnclosingQuotes = ((arg[0] !== '"') && (arg[arg.length - 1] !== '"'));
     const quote =
       arg === '' ||
       (arg.indexOf(' ') !== -1 ||
       arg.indexOf('\t') !== -1) &&
       ((arg.length > 1) &&
-      ((arg[0] !== '"') &&
-      (arg[arg.length - 1] !== '"')));
+      (hasLopsidedEnclosingQuote || hasNoEnclosingQuotes));
     if (quote) {
       result += '\"';
     }
@@ -175,3 +176,7 @@ function repeatText(text: string, count: number): string {
   }
   return result;
 }
+
+function xOr(arg1: boolean, arg2: boolean): boolean {
+  return ((arg1 && !arg2) || (!arg1 && arg2));
+}