They can log into the Gmail web interface and upload attachments fine from that. I'd say it occurs 90 of the time I am sending an email with attachment. it easy to quickly search and locate important emails and documents. It does not matter which account I send from, I experience the same problem. Capture: With harmon.ie, you simply drag and drop emails and attachments directly. I have a gmail account, gmail business account and hosted exchange account. I did notice they have Norton on there, and I'm starting to think this is an issue dealing with that, but I'm not familiar enough with that to really say definitively. I never had the this problem with the original Outlook for Mac 2011, just with the updated Version 15.
They can click the "Always trust" box, but it seems to uncheck itself. The certificate settings for look correct. I checked the IMAP settings and it all looks correct. Even if they click "Continue" it never goes through. "A secure connection cannot be established with the server etc etc etc". They can send a plain text based email fine, but when they try to send anything with an attachment (no matter the attachment size), they get this error (gmail account specific, for this message, but they can't send attachments from any of their accounts in Outlook):
A very common problem faced by Mac Users is that they are unable to download attachments in Mac Outlook 2016. However, sometimes communication via email gets disrupted due to technical errors.
5: Now, select the destination folder on your desktop. The MS Outlook is a very popular email application among Mac and Windows users for online correspondence. 4 Choose an attachment from the message option and then click on the download all option. They have several different email accounts in their Outlook (v16.48 for Mac). 2 Now, go to the email that contains an attachment which you want to download. Click Search > More > Attachment Contains. Place the cursor in the Instant Search box to activate the Search Tools. Shift to the Mail view, and open the specified mail folder where you will search keywords in the attachment content only. Close the Preferences window and take a look at your inbox your email attachments should now be visible and functioning normally. Working with a relative a few time-zones away on this one. Please follow below steps to search words within attachment content only in Microsoft Outlook.