Hi Jason C ,

Thanks for raising this—and apologies for the delay in getting back to you!

You’re not alone in experiencing issues sending paystubs or VP documents to Gmail accounts, especially when using Microsoft Outlook. Sometimes messages to Gmail may be flagged or blocked due to security filters.

Here are a few helpful resources that might apply:

•  Emails not received by Gmail recipients
•  Improve email deliverability for Gmail
•  Emailing from Sage 50 CA using Outlook – setup tips
•  Microsoft email troubleshooting

A few things that can help: 

️ Make sure you're using a supported version of Outlook
 ️ Check SPF/DKIM settings if you're on a custom domain
 ️ Ask recipients to check spam/junk folders and whitelist your sending address

Glad you found a workaround by manually resending for Gmail, but hopefully one of these steps streamlines things a bit.

If this helps, please mark it as verified :)
Let us know if the issue is still ongoing—others may benefit from the discussion too!

Hi Jason C - have you been able to resolve this issue?  I too am having issues sending paystubs to employees using Microsoft Outlook (desktop version).  I have lots of companies that I do payroll for and recently I've been getting a few emails every week that state they didn't receive their paystubs, I'm hoping the rest have all gone through(?).  I occasionally had the issue before 2025.1 update, but not many.  One or two a week is one or two too many.  It's a pretty tedious and time consuming task to send each paystub separately.

No.

Like you say, 1 or 2 is too many.  And a tedious task to send each Paystub separately.

Hi,

The links provided, though interesting, do not address the issue at hand as I am trying to send to Gmail Addresses from a non-Gmail Account.

Jason

Hi Jason C and Brenda - The Office ,

Thanks for raising this! I haven’t come across this specific combination recently, but I checked in with our Sage 50 CA support team who advised that this seems more like an Outlook-related issue rather than Sage 50, especially if other emails are sending without problems.

A quick test would be to change the recipient's email to your own—if it comes through, that would suggest Sage 50 is sending correctly. From there, you could forward it manually as a temporary workaround.

If you're using Microsoft 365 through Sage, our support team can dig deeper. If not, and it's confirmed to be outside Sage 50’s scope, it may require support from Microsoft directly.

If anyone else in the community has seen this or found a reliable fix, please chime in—we’d love to hear more tips!

If this helps, please mark it as verified :)

Fair enough.

As a note, I have since used Outlook Desktop version in 'Offline Mode' where I could add my non-Gmail E-mail address as a BCC and am receiving the messages.  So, fair enough, Sage 50 seems to be doing what it needs to do.

However, now I need to find out why Gmail is not delivering the messages.  It could be because they are being treated as spam.  On that note, I wonder if there is a way I can create multiple messages from Sage and a Gmail address to see if the Sender needs to be 'unblocked'.

Going further, I use the same process for another tool and have not received any indications those messages are not being delivered to Gmail addresses.  That leaves me to think Sage includes some code in the messages that is being picked up by Gmail and in turn prevents them from being delivered.

More testing to be done.

I have had 3 pay advices bounce back just today sent to Gmail accounts. I don’t have time to print/save them and send again. What is a solution to this problem?

Just had 8 more bounce