Last updated on September 30th, 2014

This tutorial contains detailed steps to resolve or bypass the following error in Outlook 2003, 2007 or 2007: Microsoft Outlook doesn’t always download attachments from various senders; in fact, the attachment is missing and the paper clip is not there. If the user chooses to read the e-mail through his webmail, then the attachment is there, so the error is caused by Outlook's application settings.

Since you can download the attachments in OWA, my understanding is that the attachments should be kept on the server side. The issue might be related to your outlook 2016 for Mac client side. As a result, you may give it a shot via the following aspects: 1. Clear the cache of your Office 365 account in Outlook 2016 for Mac. For attachments, Outlook 2011 can use Mac OS X’s Quick Look function to easily preview the attachment contents. While Outlook 2011 does have an updated junk mail filter, it’s still the same.

Feb 27, 2020 Notes do not display attachments in Outlook for Mac. If you move a mail message with the attachment to Notes folder, you will be not able to view it. Downloading Attachments infinite loop. Outlook for Mac downloads all attachments in Inbox folder in batches of 20, and if you let it be, the process will eventually be finished. When Office 365 users try to open or view attachments in email messages in Outlook Web App, they experience the following symptoms: In Office 365, the attachment isn't displayed in the message. Instead, a generic placeholder, such as '1 Attachment' is displayed, and this can't be opened. Use a web browser to see whether you can access Internet sites. If you are on a local network, see if you can access intranet sites. For information about checking the status of your network connections, see Mac OS Help. Solution: Verify that Outlook is online. On the Outlook menu, make sure that Work Offline is not checked.

How to resolve attachments receive problem in Outlook 2003, 2007 or 2010.

Solution 1: Modify Download Settings.

1. From Outlook main menu go to “Tools” > “Options”.

2. Choose the “Security” tab and then click “Change Automatic Download Settings”. *

* In Office 2007, 2010, navigate to “File” > “Options” > “Trust Center” > “Trust Center Settings”.

3. Uncheck the “Don’t download pictures or other content automatically in HTML e-mail” and press “OK” twice to save your settings and exit.

4. Now see if the problem is gone.

Solution 2. Modify Security settings

1. Close MS Outlook and open Internet Explorer.

2. From IE’s main menu choose “Tools” > “Internet Options”.

3. At “Security” tab, click “Trusted Sites”.

4. Click the “Default level” button to reset the Trusted sites security level to default.

5. Click “OK” to save your settings and exit. Then open Outlook and check if your problem was solved.*

* If not, perform the same procedure and set the “Trusted sites” security level to “Low”.

Solution 3. Delete Temporary Internet files.

1. Close MS Outlook and open Internet Explorer.

2. From IE’s main menu choose “Tools” > “Internet Options”.

3. At General tab under Browsing history section, press the “Delete” button.

4, At “Delete Browsing History” options, check all given options and press “Delete”.

5. When the deletion process is completed, open MS Outlook and see if your problem is solved.

Solution 4. Contact your Internet Service and Mail provider.

In some cases the Internet service (or the e-mail) provider may scan the incoming e-mails for malicious code and then remove all attachments that considered suspicious or unsafe. So contact your providers to ensure that your attachments are not removed by them.

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Mail User Guide

You can include photos, documents, and more when you write messages.

When you attach images or PDF documents, you can mark them up in Mail before you send your message.

Include photos and other files in emails


In the Mail app on your Mac, do any of the following:

  • Click the Attach button in the toolbar, locate a file (you may need to click the sidebar button to see additional folders), select it, then click Choose File.

    You can also drag files from the desktop, the Finder, or an app into your message.

  • For photos, click the Photo Browser button in the toolbar, then drag a photo into your message. You can also take a photo or scan documents, or add a sketch, using your nearby iPhone or iPad.

By default, Mail inserts images at their actual size. If different sizes are available, you can choose one from the pop-up menu located on the right side of the message header.

Auto Download Outlook Attachments

Send large email attachments using Mail Drop

You can use Mail Drop to send files that exceed the maximum size allowed by your email account provider. Mail Drop uploads large attachments to iCloud, where they’re encrypted and stored for up to 30 days.

  • If you have an iCloud account and you’re signed in to iCloud when you click Send, Mail automatically sends the attachments using Mail Drop. Mail Drop attachments don’t count against your iCloud storage.

  • If you don’t have an iCloud account, or if you’re not signed in, Mail asks you whether to use Mail Drop (to always use Mail Drop select “Don’t ask again for this account”).

If a recipient uses Mail in OS X 10.10 or later, the attachments are included in your message. For other recipients, your message includes links for downloading the attachments, and their expiration date.

You can turn Mail Drop on or off for an account. Choose Mail > Preferences, click Accounts, select the account, click Advanced, then select or deselect “Send large attachments with Mail Drop.”

See the Apple Support article Mail Drop limits.

Put email attachments at the end of messages

In the Mail app on your Mac, do one of the following:

  • For the current message: Choose Edit > Attachments > Insert Attachments at End of Message.

  • For all messages: From the Message viewer, choose Edit > Attachments > Always Insert Attachments at End of Message (a checkmark shows it’s on).

Include or exclude email attachments in replies

In the Mail app on your Mac, do one of the following:

  • Include or exclude original attachments in a reply: In the toolbar of the message window, click the Include Attachment button or the Exclude Attachment button .

  • Include or exclude original attachments in all replies: From the Message viewer, choose Edit > Attachments > Include Original Attachments in Reply (a checkmark shows it’s on). To turn it off and exclude attachments, choose the command again (the checkmark is removed).

Send email attachments to Windows users

In the Mail app on your Mac, try these suggestions:

  • Send Windows-friendly attachments. To do so for all messages, choose Edit > Attachments, then select Always Send Windows-Friendly Attachments. For a specific message, click the Attach button in the toolbar of the new message window, then select Send Windows-Friendly Attachments (if you don’t see the checkbox, click Options in the bottom corner).

  • Send documents as PDFs instead of in their original format.

  • Use filename extensions (such as .docx for a Microsoft Word document).

  • If the recipient sees two attachments (such as “MyFile” and “._MyFile”), the recipient can ignore the file with the underscore (such as “._MyFile”).

To display an attachment (such as a one-page PDF document or an image) as an icon, Control-click the attachment in your message, then choose View as Icon. To show the attachment again, Control-click it, then choose View in Place.

If the message size shown on the left side of the message header is red, the attachments are causing your message to exceed size limits set by your email account provider. Try reducing the number or size of attachments or use Mail Drop.

See alsoEmail a webpage shared from Safari in Mail on Mac