When you reply to an email in the iPhone Mail app, attachments from the original message are normally left out, which is what you want most of the time. If you need to send the file back (for example, a signed contract or an edited document), Mail can include the original attachments in your reply. This guide shows how to do that, when Mail asks, what to do if it doesn’t, and how the same thing works in Gmail and Outlook on iPhone.
Quick Answer
Open the email in Mail, tap the Reply arrow, and choose Reply or Reply All. When Mail asks Include attachments from original message?, tap Include. If you don’t see the prompt, use Forward instead and enter the sender’s address, since forwarding always keeps attachments.
How to Include Attachments When Replying in Mail
- Open the Mail app and tap the email with the attachment.
- Wait for the attachment to download fully (tap it once if it shows “Tap to Download”).
- Tap the Reply arrow at the bottom of the screen.
- Choose Reply or Reply All.
- When prompted, tap Include. The attachment appears in the quoted message.
- Type your reply and tap the blue Send arrow.
Mail usually shows the prompt only when the original attachments are downloaded and the message is replied to with its original content quoted.
No Prompt? Use Forward Instead
- Tap the Reply arrow > Forward.
- Tap Include if asked about attachments.
- In To, type the original sender’s name or address.
- Edit the subject from “Fwd:” to “Re:” if you like, then send.
Attach the File Again Manually
- In the original email, touch and hold the attachment and tap Save to Files (or tap Share > Save to Files).
- Start your reply, then tap in the message body.
- Tap the < arrow above the keyboard (or the format bar) and choose the document icon to attach from Files, or the photo icon for images.
- Select the file and send.
This is also how you send an edited version, such as a PDF you signed with Markup. Tip: tap a PDF attachment, tap the Markup pen, sign it, then tap Done > Reply to All to send the signed copy back automatically.
Gmail and Outlook Apps
- Gmail app: Reply doesn’t include attachments. Tap Forward to keep them, or tap the paperclip in the reply to attach a file.
- Outlook app: Reply doesn’t include the original attachments either. Use Forward, or tap the paperclip to attach a file from your phone or cloud storage.
Troubleshooting
- Attachment missing after tapping Include: make sure the attachment finished downloading before replying.
- File too large to send: Mail offers Mail Drop for large files (up to 5 GB) if you use iCloud. Otherwise, share a link from iCloud Drive or another cloud service.
- Recipient says the file is broken: some winmail.dat attachments from Outlook can’t be forwarded correctly; ask the sender to resend as PDF.
Frequently Asked Questions
Why doesn’t Reply include attachments by default?
It avoids sending large files back to someone who already has them.
Does this work on iPad?
Yes. The Mail app on iPad works the same way.
Can I include only one of several attachments?
After including them, touch and hold an attachment in the draft and delete the ones you don’t need.
Summary
- Open the email and let the attachment download.
- Tap Reply and choose Include when asked.
- If there’s no prompt, forward the email to the sender.
- Or save the file and attach it manually.
Kermit Matthews is a freelance writer based in Philadelphia, Pennsylvania with more than a decade of experience writing technology guides. He has a Bachelor’s and Master’s degree in Computer Science and has spent much of his professional career in IT management.
He specializes in writing content about iPhones, Android devices, Microsoft Office, and many other popular applications and devices.