diff --git a/.changeset/windows-prompt-underline.md b/.changeset/windows-prompt-underline.md
new file mode 100644
index 00000000000..daa7b2a0f74
--- /dev/null
+++ b/.changeset/windows-prompt-underline.md
@@ -0,0 +1,5 @@
+---
+'@shopify/cli-kit': patch
+---
+
+Fix text prompt underlines rendering as unsupported characters in Windows consoles.
diff --git a/packages/cli-kit/src/private/node/ui/components/DangerousConfirmationPrompt.test.tsx b/packages/cli-kit/src/private/node/ui/components/DangerousConfirmationPrompt.test.tsx
index b5eb3fc0d7e..69ac5628d5b 100644
--- a/packages/cli-kit/src/private/node/ui/components/DangerousConfirmationPrompt.test.tsx
+++ b/packages/cli-kit/src/private/node/ui/components/DangerousConfirmationPrompt.test.tsx
@@ -1,14 +1,37 @@
 import {DangerousConfirmationPrompt} from './DangerousConfirmationPrompt.js'
 import {getLastFrameAfterUnmount, sendInputAndWaitForChange, waitForInputsToBeReady, render} from '../../testing/ui.js'
 import {unstyled} from '../../../../public/node/output.js'
+import colors from '../../../../public/node/colors.js'
+import {platformAndArch} from '../../../../public/node/os.js'
 import React from 'react'
 
-import {describe, expect, test, vi} from 'vitest'
+import {beforeEach, describe, expect, test, vi} from 'vitest'
+
+vi.mock('../../../../public/node/os.js')
+
+beforeEach(() => {
+  vi.mocked(platformAndArch).mockReturnValue({platform: 'darwin', arch: 'arm64'})
+})
 
 const ENTER = '\r'
 const ESC = '\x1b'
 
 describe('DangerousConfirmationPrompt', () => {
+  test.each(['windows', 'darwin', 'linux'] as const)('renders the underline on %s', async (platform) => {
+    vi.mocked(platformAndArch).mockReturnValue({platform, arch: 'amd64'})
+    const renderInstance = render(
+      <DangerousConfirmationPrompt onSubmit={() => {}} message="Test question" confirmation="yes" />,
+    )
+    const underline = (platform === 'windows' ? '─' : '▔').repeat(77)
+
+    expect(renderInstance.lastFrame()).toContain(colors.cyan(underline))
+
+    await waitForInputsToBeReady()
+    await sendInputAndWaitForChange(renderInstance, ENTER)
+
+    expect(renderInstance.lastFrame()).toContain(colors.red(underline))
+  })
+
   test('default state', () => {
     const {lastFrame} = render(
       <DangerousConfirmationPrompt onSubmit={() => {}} message="Test question" confirmation="yes" />,
diff --git a/packages/cli-kit/src/private/node/ui/components/DangerousConfirmationPrompt.tsx b/packages/cli-kit/src/private/node/ui/components/DangerousConfirmationPrompt.tsx
index dfeda4abbe5..73abcf5fe25 100644
--- a/packages/cli-kit/src/private/node/ui/components/DangerousConfirmationPrompt.tsx
+++ b/packages/cli-kit/src/private/node/ui/components/DangerousConfirmationPrompt.tsx
@@ -5,6 +5,7 @@ import {handleCtrlC, useComplete} from '../../ui.js'
 import useLayout from '../hooks/use-layout.js'
 import {messageWithPunctuation} from '../utilities.js'
 import {AbortSignal} from '../../../../public/node/abort.js'
+import {platformAndArch} from '../../../../public/node/os.js'
 import useAbortSignal from '../hooks/use-abort-signal.js'
 import usePrompt, {PromptState} from '../hooks/use-prompt.js'
 
@@ -44,7 +45,6 @@ const DangerousConfirmationPrompt: FunctionComponent<DangerousConfirmationPrompt
   const complete = useComplete()
   const [error, setError] = useState<TokenItem<InlineToken> | undefined>(undefined)
   const color = promptState === PromptState.Error ? 'red' : 'cyan'
-  const underline = new Array(oneThird - 3).fill('▔')
   const {isAborted} = useAbortSignal(abortSignal)
 
   useInput((input, key) => {
@@ -133,9 +133,20 @@ const DangerousConfirmationPrompt: FunctionComponent<DangerousConfirmationPrompt
                 />
               </Box>
             </Box>
-            <Box marginLeft={3}>
-              <Text color={color}>{underline}</Text>
-            </Box>
+            {platformAndArch().platform === 'windows' ? (
+              <Box
+                marginLeft={3}
+                borderStyle="single"
+                borderColor={color}
+                borderBottom={false}
+                borderLeft={false}
+                borderRight={false}
+              />
+            ) : (
+              <Box marginLeft={3}>
+                <Text color={color}>{'▔'.repeat(oneThird - 3)}</Text>
+              </Box>
+            )}
             {promptState === PromptState.Error && error ? (
               <Box marginLeft={3}>
                 <Text color={color}>
diff --git a/packages/cli-kit/src/private/node/ui/components/TextPrompt.test.tsx b/packages/cli-kit/src/private/node/ui/components/TextPrompt.test.tsx
index 939cec7006e..b41b31b0842 100644
--- a/packages/cli-kit/src/private/node/ui/components/TextPrompt.test.tsx
+++ b/packages/cli-kit/src/private/node/ui/components/TextPrompt.test.tsx
@@ -3,13 +3,33 @@ import {getLastFrameAfterUnmount, sendInputAndWaitForChange, waitForInputsToBeRe
 import {unstyled} from '../../../../public/node/output.js'
 import {AbortController} from '../../../../public/node/abort.js'
 import colors from '../../../../public/node/colors.js'
+import {platformAndArch} from '../../../../public/node/os.js'
 import React from 'react'
 
-import {describe, expect, test, vi} from 'vitest'
+import {beforeEach, describe, expect, test, vi} from 'vitest'
+
+vi.mock('../../../../public/node/os.js')
+
+beforeEach(() => {
+  vi.mocked(platformAndArch).mockReturnValue({platform: 'darwin', arch: 'arm64'})
+})
 
 const ENTER = '\r'
 
 describe('TextPrompt', () => {
+  test.each(['windows', 'darwin', 'linux'] as const)('renders the underline on %s', async (platform) => {
+    vi.mocked(platformAndArch).mockReturnValue({platform, arch: 'amd64'})
+    const renderInstance = render(<TextPrompt onSubmit={() => {}} message="Test question" />)
+    const underline = (platform === 'windows' ? '─' : '▔').repeat(77)
+
+    expect(renderInstance.lastFrame()).toContain(colors.cyan(underline))
+
+    await waitForInputsToBeReady()
+    await sendInputAndWaitForChange(renderInstance, ENTER)
+
+    expect(renderInstance.lastFrame()).toContain(colors.red(underline))
+  })
+
   test('default state', () => {
     const {lastFrame} = render(<TextPrompt onSubmit={() => {}} message="Test question" defaultValue="Placeholder" />)
 
diff --git a/packages/cli-kit/src/private/node/ui/components/TextPrompt.tsx b/packages/cli-kit/src/private/node/ui/components/TextPrompt.tsx
index 37e24221c94..1ca5f5a4749 100644
--- a/packages/cli-kit/src/private/node/ui/components/TextPrompt.tsx
+++ b/packages/cli-kit/src/private/node/ui/components/TextPrompt.tsx
@@ -4,6 +4,7 @@ import {handleCtrlC, useComplete} from '../../ui.js'
 import useLayout from '../hooks/use-layout.js'
 import {messageWithPunctuation} from '../utilities.js'
 import {AbortSignal} from '../../../../public/node/abort.js'
+import {platformAndArch} from '../../../../public/node/os.js'
 import useAbortSignal from '../hooks/use-abort-signal.js'
 import usePrompt, {PromptState} from '../hooks/use-prompt.js'
 import React, {FunctionComponent, useCallback, useEffect, useState} from 'react'
@@ -64,7 +65,6 @@ const TextPrompt: FunctionComponent<TextPromptProps> = ({
   const complete = useComplete()
   const [error, setError] = useState<string | undefined>(undefined)
   const color = promptState === PromptState.Error ? 'red' : 'cyan'
-  const underline = new Array(oneThird - 3).fill('▔')
   const {isAborted} = useAbortSignal(abortSignal)
 
   useInput((input, key) => {
@@ -128,9 +128,20 @@ const TextPrompt: FunctionComponent<TextPromptProps> = ({
               />
             </Box>
           </Box>
-          <Box marginLeft={3}>
-            <Text color={color}>{underline}</Text>
-          </Box>
+          {platformAndArch().platform === 'windows' ? (
+            <Box
+              marginLeft={3}
+              borderStyle="single"
+              borderColor={color}
+              borderBottom={false}
+              borderLeft={false}
+              borderRight={false}
+            />
+          ) : (
+            <Box marginLeft={3}>
+              <Text color={color}>{'▔'.repeat(oneThird - 3)}</Text>
+            </Box>
+          )}
           {promptState === PromptState.Error ? (
             <Box marginLeft={3}>
               <Text color={color}>{error}</Text>