Apple Mail Not Showing Attachments on Mac? How to Fix It (2026)

When the Mail app on your Mac doesn't show an attachment, the file is usually there in a form you didn't expect: Mail displays images and one-page PDFs inside the message instead of as an icon, the account only downloads some file types, the account is offline, or the sender's app wrapped the file in winmail.dat. The first three take a minute in Mail's own menus; the last one needs the sender.

It's an irritating problem because it looks like nothing happened. Someone says "it's attached," you see a paperclip or a line of text, and no file. Below is how to tell which of the causes you're looking at, the fix for each in macOS, where Mail keeps the files once they do arrive, and what to ask the sender when the problem is on their side.

Quick diagnosis: what you see and what it means

Match what's on your screen to a row, then jump to that section. The causes come from Apple's Mail User Guide and Microsoft's article on message formats.

Why Apple Mail shows an attachment inside the message

Apple Mail displays some attachments, such as images and one-page PDFs, directly in the body of the email rather than as a file icon, according to Apple's guide to viewing attachments. The file is attached; it just doesn't look like one, and it still trips me up. A contract I was waiting for once arrived as what looked like a plain letter, and I scrolled up and down for a while before I realized the whole message body was the PDF.

To switch an inline attachment to an icon:

1. Open the message in Mail.
2. Control-click the image or PDF in the body.
3. Choose View as Icon.

To go back, Control-click the icon and choose View in Place. Either way, you can preview the file without opening another app by selecting it and pressing the Space bar, or by force clicking it on a trackpad that supports it. To open it in a specific app, Control-click it and choose Open With.

How to make Apple Mail download every attachment

Apple Mail decides which attachments to download for each account with the Download Attachments setting in Mail > Settings > Accounts > Account Information. Media files (images, PDFs, video and audio) always download, per Apple's Account Information settings page. Other files, such as spreadsheets and zip archives, follow the option you pick.

• All: Mail always downloads these attachments.
• Recent: Mail downloads only attachments of this type received in the past 15 months.
• None: Mail doesn't download them.

So if photos come through but an old Excel file or a zip doesn't, this setting is the first suspect. To change it:

1. In Mail, choose Mail > Settings.
2. Click Accounts, then select the account the message arrived in.
3. Click Account Information.
4. Set Download Attachments to All.
5. Close the window and reopen the message.

On my work account I leave this on All. Disk space is cheaper than the minute I lose wondering where a spreadsheet went, and with Recent, a file from a project two years ago is exactly the one that won't be there when I search for it. The trade-off is space on your Mac, so on a small drive, Recent is a fair compromise for a personal account.

Bring an offline Apple Mail account back online

An offline account can't fetch attachments that haven't downloaded yet. Apple Mail marks an offline account with a lightning bolt icon next to its mailboxes in the sidebar, according to Apple's page on offline mailboxes. Settings shows the same thing as a red status dot, where green means online (Account Information settings).

1. Click the lightning bolt next to the account, or choose Mailbox > Take All Accounts Online.
2. With several accounts, you can bring just one back with Mailbox > Online Status, then the account's name.
3. If it stays offline, check that your Mac is connected to the internet.
4. If a warning icon appears next to the account name, click it to open Connection Doctor.

You can also open Connection Doctor any time from Window > Connection Doctor. Apple's Connection Doctor guide says to follow the instructions in its Details column; double-clicking that text opens the account in Mail's settings. Click Show Detail, then Check Again, to watch the connection log while Mail retries. If it still fails, Apple suggests contacting your email provider to check your account details. Our guide to Apple Mail not sending emails covers the account and server side in more depth.

Rebuild the mailbox when attachments look missing or garbled

Rebuilding a mailbox makes Apple Mail refresh its list of messages, and Apple recommends it when messages appear missing or garbled (Apple's rebuild instructions). It's the fix to try when one attachment shows a blank icon or a whole folder of messages behaves oddly, after the settings above check out.

1. In the Mail sidebar, select the mailbox that has the problem (Inbox, for example).
2. Choose Mailbox > Rebuild.
3. Wait for Mail to finish before opening the message again.

I rebuild only the one folder that's acting up rather than every mailbox at once. Apple's page doesn't spell out what a rebuild does to each kind of account, but it does note that Time Machine can restore what Mail downloaded, so if any of your mail lives only on this Mac (in an On My Mac mailbox, say), I'd make sure a recent backup exists before you start.

Check webmail before you blame your Mac

Opening the same message in your provider's website (Gmail, iCloud Mail at icloud.com, Outlook.com) tells you in seconds whether the problem is Apple Mail or the email itself. If the file is there on the web, the fix is on your Mac, in one of the sections above. If it's missing on the web too, no setting on your Mac will bring it back.

In the second case, the problem started before the message reached you: the sender forgot to attach it, or their email service refused the file. Gmail, for example, won't let anyone attach certain file types, including .exe, .dmg and .iso, and blocks them inside zip files too, according to Google's list of blocked file types. Google's suggested workaround is sharing the file through Google Drive instead. This webmail check is now the first thing I do, because it splits the problem in half before I touch a single setting.

Attachment shows up as winmail.dat or ATT00001.dat

A file named winmail.dat, or one with a generic name like ATT00001.dat, means the sender used Rich Text format in Microsoft Outlook. Outlook packages Rich Text messages with Transport Neutral Encapsulation Format (TNEF), and apps that aren't built on Microsoft Exchange, Apple Mail among them, can fail to read it, as Microsoft explains in its article on message formats. The real attachments are often packed inside that .dat file.

The clean fix is on the sender's side, and Microsoft lists it as the solution when a recipient "doesn't receive regular file attachments":

• For one message: in Outlook for Windows, open the message, go to the Format Text tab, choose Message Format, and pick HTML or Plain Text.
• For every message: in Outlook, choose File > Options > Mail and set Compose messages in this format to HTML or Plain Text.

Microsoft also notes that the winmail.dat file carries the path of the sender's Outlook data file and their sign-in name, which is one more reason to ask for a resend instead of hunting for a converter. When I've had to ask a client for this, I keep it short and practical so nobody feels told off:

Hi,

Your attachment came through as a file called winmail.dat on my Mac, so I can't open it. Could you resend it with the message set to HTML? In Outlook it's on the Format Text tab, under Message Format.

Thanks,
[Your name]

A download link instead of an attachment: Mail Drop

If the email has a link where you expected a file, the sender probably used Mail Drop, Apple's way of sending large files through iCloud. Mail Drop handles attachments up to 5 GB, and recipients have 30 days to download them, according to Apple's Mail Drop limits page. After that the files expire, so download them promptly and ask for a new copy if the link has run out.

Mail Drop kicks in when a message is bigger than the sender's email provider allows. With an iCloud account Mail uses it automatically, and with other accounts Mail asks first, per Apple's guide to sending attachments. Apple also notes that heavy download traffic can stop recipients from reaching a link, so a link that fails once is worth trying again later.

When the attachments were removed on purpose

Apple Mail has a Message > Remove Attachments command, and on IMAP accounts it deletes the files from the mail server too, so they can't be recovered, according to Apple's attachments guide. The message stays in your mailbox, marked to show its attachments were removed. If that's what you're looking at, the only way back is asking the sender to send the file again.

Deleting a message also deletes its attachment from Mail, though Apple says Mail doesn't delete attachments you've already saved somewhere else.

Where Apple Mail saves attachments on a Mac

Attachments you save from Apple Mail go to your Downloads folder by default, and you can choose a different folder in Mail > Settings > General > Downloads folder (Apple's General settings page). Files Mail downloads automatically, before you save them, live in a special folder inside your home Library folder (Account Information settings), and by default those copies are deleted when you delete the message, unless you change Remove unedited downloads in the same General pane.

To save attachments, per Apple's attachments guide:

1. Select the message and hover over its header.
2. Click the Attach button, then click one file's name or choose Save All.
3. Pick a folder and click Save.

You can also choose File > Save Attachments, or drag an attachment straight onto the desktop. When I need a file from months ago and can't remember the subject line, searching beats scrolling; our guide to Apple Mail search and Smart Mailboxes covers how to narrow a search down to messages with attachments.

Make sure your own attachments show up for others

The same problem runs the other way: a file you send from a Mac can look odd to someone on Windows. Apple Mail has two settings for this, both in Edit > Attachments in Apple's guide to sending attachments:

• Always Send Windows-Friendly Attachments for every message, or Send Windows-Friendly Attachments from the Attach button for just one.
• Always Insert Attachments at End of Message, which keeps files below your text instead of wherever the cursor was.

Apple also suggests sending documents as PDFs and keeping filename extensions like .docx, so the other person's computer knows what to open them with. Before a proposal goes to a client I don't know well, I export it to PDF. It's the format least likely to arrive looking different from what I sent.

A short checklist for next time

• Look for the file in the body first; Mail shows images and one-page PDFs in place.
• Open the message in webmail to see whether the file exists at all.
• Set Download Attachments to All on the accounts where files matter.
• Watch for a lightning bolt in the sidebar and use Mailbox > Take All Accounts Online.
• Rebuild only the mailbox that's misbehaving.
• Download Mail Drop files within 30 days.
• Ask Outlook senders to switch to HTML when you get winmail.dat.

New to Mail, or setting up a second account? Our Apple Mail guide walks through accounts and the settings worth changing, and Gmail vs. Apple Mail helps if you're deciding whether to keep reading Gmail in Mail at all.