diff --git a/src/actions/commands/commandLine.ts b/src/actions/commands/commandLine.ts
index 6b455fc6383..d922e2d6702 100644
--- a/src/actions/commands/commandLine.ts
+++ b/src/actions/commands/commandLine.ts
@@ -115,9 +115,14 @@ class CommandLineTab extends CommandLineAction {
         isRemote,
         shouldAddDotItems
       );
+      const startWithBaseNameRegex = new RegExp(
+        `^${baseName}`,
+        process.platform === 'win32' ? 'i' : ''
+      );
       newCompletionItems = dirItems
-        .filter((name) => name.startsWith(baseName))
-        .map((name) => name.slice(name.search(baseName) + baseName.length))
+        .map((name): [RegExpExecArray | null, string] => [startWithBaseNameRegex.exec(name), name])
+        .filter(([isMatch]) => isMatch !== null)
+        .map(([match, name]) => name.slice(match![0].length))
         .sort();
     }
 
diff --git a/test/cmd_line/tabCompletion.test.ts b/test/cmd_line/tabCompletion.test.ts
index 1d8fa054a82..d594d65f42a 100644
--- a/test/cmd_line/tabCompletion.test.ts
+++ b/test/cmd_line/tabCompletion.test.ts
@@ -279,4 +279,37 @@ suite('cmd_line tabComplete', () => {
       await t.removeFile(spacedFilePath);
     }
   });
+
+  test('command line file tab completion case-sensitivity platform dependent', async () => {
+    const dirPath = await t.createRandomDir();
+    const filePath = await t.createEmptyFile(join(dirPath, 'testfile'));
+    const fileAsTyped = join(dirPath, 'TESTFIL');
+    const cmd = `:e ${fileAsTyped}`.split('');
+
+    try {
+      if (process.platform === 'win32') {
+        await modeHandler.handleMultipleKeyEvents(cmd);
+        await modeHandler.handleKeyEvent('<tab>');
+        const statusBarAfterTab = StatusBar.getText().trim();
+        await modeHandler.handleKeyEvent('<Esc>');
+        assert.strictEqual(
+          statusBarAfterTab.toLowerCase(),
+          `:e ${filePath}|`.toLowerCase(),
+          'Cannot complete path case-insensitive on windows'
+        );
+      }
+      else {
+        await modeHandler.handleMultipleKeyEvents(cmd);
+        const statusBarBeforeTab = StatusBar.getText();
+        await modeHandler.handleKeyEvent('<tab>');
+        const statusBarAfterTab = StatusBar.getText().trim();
+        await modeHandler.handleKeyEvent('<Esc>');
+        assert.strictEqual(statusBarBeforeTab, statusBarAfterTab, 'Is case-insensitive on non-windows');
+      }
+
+    } finally {
+      await t.removeFile(filePath);
+      await t.removeDir(dirPath);
+    }
+  });
 });