diff --git a/src/Virtual.ts b/src/Virtual.ts
index 93ba42f..051de4a 100644
--- a/src/Virtual.ts
+++ b/src/Virtual.ts
@@ -897,9 +897,19 @@ export class Virtual {
       }
     });
 
+    const isShiftPressed = modifiers.some(
+      (modifier) => MacOSModifiers[modifier] === "shift"
+    );
+
     const keyboardCommand = [
       ...modifiers.map((modifier) => `{${modifier}>}`),
-      ...keys.map((key) => `{${key}}`),
+      ...keys.map((key) => {
+        if (key.length === 1) {
+          return isShiftPressed ? key.toUpperCase() : key;
+        }
+
+        return `{${key}}`;
+      }),
       ...modifiers.reverse().map((modifier) => `{/${modifier}}`),
     ].join("");
 
diff --git a/test/int/press.int.test.ts b/test/int/press.int.test.ts
index 44e6b40..a9bcb5b 100644
--- a/test/int/press.int.test.ts
+++ b/test/int/press.int.test.ts
@@ -35,9 +35,8 @@ describe("press", () => {
     expect(await virtual.itemText()).toEqual("Input Some Text");
 
     await virtual.press("Shift+a+b+c");
-    // TODO: FAIL Testing Library user-event doesn't support modification yet, this should be "ABC"
-    expect(getByRole(container, "textbox")).toHaveValue("abc");
-    expect(await virtual.itemText()).toEqual("Input Some Text, abc");
+    expect(getByRole(container, "textbox")).toHaveValue("ABC");
+    expect(await virtual.itemText()).toEqual("Input Some Text, ABC");
 
     await virtual.stop();
   });
@@ -80,11 +79,93 @@ describe("press", () => {
     expect(await virtual.itemText()).toEqual("Input Some Text");
 
     await virtual.press("Shift+a+b+c");
-    // TODO: FAIL Testing Library user-event doesn't support modification yet, this should be "ABC"
-    expect(getByRole(container, "textbox")).toHaveValue("abc");
-    expect(await virtual.itemText()).toEqual("Input Some Text, abc");
+    expect(getByRole(container, "textbox")).toHaveValue("ABC");
+    expect(await virtual.itemText()).toEqual("Input Some Text, ABC");
     expect(advanceTimers).toHaveBeenCalled();
 
     await virtual.stop();
   });
+
+  it("should capitalise single character keys when Shift is pressed", async () => {
+    const container = document.body;
+
+    await virtual.start({ container });
+
+    await virtual.next();
+    await virtual.next();
+
+    expect(await virtual.itemText()).toEqual("Input Some Text");
+
+    await virtual.press("Shift+a");
+    expect(getByRole(container, "textbox")).toHaveValue("A");
+    expect(await virtual.itemText()).toEqual("Input Some Text, A");
+
+    await virtual.stop();
+  });
+
+  it("should preserve uppercase for single character keys already uppercase when Shift is pressed", async () => {
+    const container = document.body;
+
+    await virtual.start({ container });
+
+    await virtual.next();
+    await virtual.next();
+
+    expect(await virtual.itemText()).toEqual("Input Some Text");
+
+    await virtual.press("Shift+A");
+    expect(getByRole(container, "textbox")).toHaveValue("A");
+    expect(await virtual.itemText()).toEqual("Input Some Text, A");
+
+    await virtual.stop();
+  });
+
+  it("should not capitalise single character keys when Shift is not pressed", async () => {
+    const container = document.body;
+
+    await virtual.start({ container });
+
+    await virtual.next();
+    await virtual.next();
+
+    expect(await virtual.itemText()).toEqual("Input Some Text");
+
+    await virtual.press("a");
+    expect(getByRole(container, "textbox")).toHaveValue("a");
+    expect(await virtual.itemText()).toEqual("Input Some Text, a");
+
+    await virtual.stop();
+  });
+
+  it("should handle non-shift modifiers when pressing single character keys", async () => {
+    const container = document.body;
+
+    await virtual.start({ container });
+
+    await virtual.next();
+    await virtual.next();
+
+    expect(await virtual.itemText()).toEqual("Input Some Text");
+
+    await virtual.press("Control+a");
+    expect(getByRole(container, "textbox")).toHaveValue("");
+
+    await virtual.stop();
+  });
+
+  it("should handle multi-character keys when Shift is pressed", async () => {
+    const container = document.body;
+
+    await virtual.start({ container });
+
+    await virtual.next();
+    await virtual.next();
+
+    expect(await virtual.itemText()).toEqual("Input Some Text");
+
+    await virtual.press("Shift+Enter");
+    expect(getByRole(container, "textbox")).toHaveValue("");
+
+    await virtual.stop();
+  });
 });