Paperless Office e-mails not sending after June 1st using Office365

We have not been able to send any automatic paperless office e-mails (Customer Invoices, Payroll Stubs) since June 1st. Our e-mail configuration in Sage 100 uses smtp.office365.com as the mail server.  We have not changed anything with this setup since we started using this feature over 2 years ago.   I know Microsoft was going to implement some TLS changes starting June 1st (I think disabling TLS 1.0 and 1.1 support).  Everything worked just fine for us on Friday the 29th of May.  I have reached out to Sage support and they are telling me I'm the only one who has reported this issue and haven't been able to figure out why we can't send e-mails.

What's weird is every time I do a test e-mail from company maintenance it errors out with the following error:

Failed to read beginning of SSL/TLS record.
b: 0
dbSize: 0
nReadNBytes: 0
idleTimeoutMs: 30000
--readHandshakeMessages
--clientHandshake2
--clientHandshake
Client handshake failed. (1)
connectionClosed: 0
Failed to establish TLS connection

When we try and send customer invoices we get the same error we get when doing a test e-mail, but when we do payroll, we do not get any errors.  Yesterday when i did payroll I checked our sent items folder and only 4 employee e-mails were sent out of 17.  I originally thought the issue could be with our firewall (Fortigate), but if the firewall was blocking things, then the 4 e-mails that were sent shoudn't have been.

If anyone out there has any ideas of what could be going on, we would really appreciate some help.  I'm still waiting for support to provide me with information on exactly what Sage 100 is doing in the background when sending e-mails, so I can contact Fortinet or even Microsoft to figure this out.

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    Works for us.  For address we have: outlook.office365.com  and the port is 587

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    BigLouie, thanks for the reply!  Yeah we have tried it using outlook.office365.com and get the same error.  Support had me test it using my personal Gmail account, so I configured using gmail and it worked fine if I was using SSL, but as soon as I switched to TLS gmail failed.  Need to determine where the failure is coming from, our Vipre AV Firewall, our Fortinet Firewall or something with our Office365 account.   When I did a wireshark on my PC during our initial testing, it seems that we are connecting using TLS 1.2.

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    You are not the only one.  I have a client with the same issue. They use Office 365, some go, some don't.  Sage support said it was an issue on the clients side and that they couldn't help.  It seemed to have started right after the client implemented 2-factor on their email. 

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    Sued2, thanks for the reply!  Sage 100 thought the same thing, but we do not have 2FA active on our Office365 account, I logged into my portal and confirmed this.  I may have to reach back out to Microsoft again.  The first time I did, they were absolutely no help, go figure!

  • 0 in reply to ktager

    Ktager or Sued2 reaching out to see how you resolved this issue? This started for us a about a week ago. Some emails deliver others get an error, click on proceed and about 5 - 10 more are sent. The pdf is created and can be emailed from the customer viewer, just seems to happen during invoice printing.

  • 0 in reply to ldion

    Idion,

    We didn't end up doing anything.  Microsoft supposedly reversed what they did on the Office365 servers that stopped the e-mails from working originally.  Could never get an answer to exactly what they did that was preventing them from sending.  Once they did this we haven't had any issues sending e-mails with Paperless office in Sage 100.  Below are our settings in Sage 100.  You may need to reach out to Office365 support to inquire.  Sorry I couldn't be of more help.