Sage 100

Since late July, the client has been getting messages (failures) when sending Paperless invoices thru Office 365, but we cannot pinpoint anything that's changed. (Actually, about a month or two before this, I put up Visual Cut and set up some reports and auto emails; cannot imagine how that would interfere.) They typically send about 60-80 invoice emails in a batch and most go thru, but they could get the message if they just send 4 invoices. Our IT group tells me that O365 has a 30 email/minute limitation and that's the issue, but the messages come up even if below 30. They customer is running Sage 4.40.6 (highly modified) on Server 2008 R2, which we moved them to months ago. Any ideas? Thanks in advance, Roberta Samples of messages: Unable to verify SMTP connection. ChilkatLog: VerifySmtpConnection: Checking connectivity to SMTP server customer-com.mail.protection.outlook.com:25 smtp_host: customer-com.mail.protection.outlook.com smtp_port: 25 WaitForData timed out. Failed to get initial response The SMTP server may be denying access for this domain. (there may be more to this message, but it's all the customer sent me.) OR Unable to login to SMTP connection. ChikatLog: VerifySMTPLogin SMTP_Connect Connsecting to SMTP Server customer-com.mailprotection.outlook.com:25 smtp_host:customer-com.mail.protection.outlook.com smtp_port:25 domain: customer smtp_user: customeradmin An existing connection was forcibly closed by the remote host. Failed to receive on the TCP socket EHLO failed, sending HELO... SocketError: unknown socket error Error sending on socket send_size:26 Failed to send Hello Failed to connect to SMTP server.

It sounds like you're trying to use Option #1 from this page (https://technet.microsoft.com/en-us/library/dn554323(v=exchg.150).aspx#option1) so the smtp host should be SMTP.OFFICE365.COM (not the MX record alias), TLS should be used (port 587 is recommended, though it appears 25 is working for you) and the full username (admin@customer.com) should be entered. There's more specific details here (https://technet.microsoft.com/en-us/library/dn554323(v=exchg.150).aspx#HowtoconfigSMTPCS)

Thanks, Steve. I sent this info to our IT group. With V440 there is no SMTP encryption options. I'll post an update once we get this working all the time.

With older versions of MAS and Office 365 we've had to use an SMTP relay to get around the lack of TLS option for Paperless email.

Thank you both; it is working now. The IT group made a couple of changes after I sent them your information: 1. Removed the authentication for the email direct send in Company Maintenance 2. Added the external ip address to the relay in Office 365 3. Updated the spf record in DNS to include customer's external IP address to validate email coming from customer into Office 365. This change permits email coming from customer's external ip to be relay through Office 365.