emails with attachments never arrive, without attachments they do..

I have a couple of people at a client that often have issues receiving attachments in emails.

The email will not arrive at all. Most are running Outlook 2013 or 2016. It will not arrive on their iDevices either.

They have no junk-mail enabled in their Outlook only a spam service where the emails do not get caught either.

The same person tries to send an email without an attachment and it arrives.

This is from several different people sending to two different employees at the client.

I've heard people talk about Outlook misunderstanding the coding of the attachments but usually then the email arrives with a winmail.dat attached or similar.
KaiAsked:
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xtermieCommented:
Hi!  Please try working in safe-mode with networking and check if you are able to send emails with attachments - to start in safe mode
Hold Ctrl (keep it held down while application launches) and then click the outlook icon to start it, say yes when asked if you want to start in safe mode.
Note: After you have finished troubleshooting in Safemode with networking, ensure you restart the computer in normal mode.

If issue resolves in safe-mode with networking then this might be due to security settings on the computer causing this issue

Also, are you scanning mail with mcafee? That can cause issues, too
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JohnBusiness Consultant (Owner)Commented:
Are the attachments bigger than the allowance of the mail server?  That is a very common reason.
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KaiAuthor Commented:
No they are usually 1 or 2 page PDF's. The Server has a 25MB limit on attachments...
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Sajid Shaik MSr. System AdminCommented:
do u have any firewall in between ? or any email security ? check there...

all the best
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xtermieCommented:
If safe mode does not work you could try creating a new profile as profiles seem to get corrupt over time.  To create a new Outlook profile via the steps this article:

https://support.microsoft.com/en-us/kb/829918

Generally, this will not interfere with your existing files, and for fear of losing data, you can export the data files to a PST file referring to the article below:

https://support.office.com/en-us/article/Export-or-backup-email-contacts-and-calendar-to-an-Outlook-pst-file-14252b52-3075-4e9b-be4e-ff9ef1068f91
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xtermieCommented:
good options and suggestions provided
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