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Sage 100 Paperless Email Electronic Delivery Failing With Rackspace

November 8, 2022 by Wayne Schulz

We have had two of our customers – both using Rackspace – secure.emailsrvr.com – call to report Sage 100 Paperless Email errors. In both cases they suddenly couldn’t use electronic delivery to send Sage 100 paperless office forms.

Fortunately there is a fast fix which you can perform yourself to completely resolve this problem.

A paperless email error mean that critical forms such as sales orders, invoices, purchase orders and payroll stubs suddenly stop going out over the company’s SMTP email connection.

The first (and most common) cause of this type of error is a login password that was changed for the account used to send email in Sage 100.

If you can verify that no account password changes have happened then the resolution might be the same one that I found worked for both of these customers.

The Sage 100 Paperless Email Error Message

In all cases when Sage 100 cannot send an email it will generate a very lengthy and somewhat confusing error message. The error message may look similar to below.

If you are using secure.emailsrvr.com as your SMTP outgoing email connection and your error matches the one shown below then there’s a good chance this fix will resolve your issue.

Here’s the error which both my customers received. I’ve removed only the smtp_user: field and replaced it with [email address here]. In actuality your error message will include the name of the email account being used to send mail.

Unable to login to SMTP connection.
ChilkatLog:
  VerifySmtpLogin:
    DllDate: Jan 19 2012
    UnlockPrefix: SBestSoftMAILQ
    Username: RECOS02:Accountant
    Architecture: Little Endian; 32-bit
    Language: ActiveX
    Need new SMTP connection
    checkForExistingConnection: Elapsed time: 0 millisec
    SMTP_Connect:
      Connecting to SMTP server secure.emailsrvr.com:25
      smtp_host: secure.emailsrvr.com
      smtp_port: 25
      smtp_user: [email address here]
      ConnectTimeoutMs_1: 30000
      calling ConnectSocket2
      IPV6 enabled connect with NO heartbeat.
      connectingTo: secure.emailsrvr.com
      dnsCacheLookup: secure.emailsrvr.com
      dnsCacheHit: 173.203.187.10
      GetHostByNameHB_ipv4: Elapsed time: 0 millisec
      maxTimeMs_connect: 30000
      myIP_1: 210.105.50.10
      myPort_1: 50785
      connect successful (1)
      socketConnect: Elapsed time: 31 millisec
      InitialResponse: 220 smtp5.relay.iad3a.emailsrvr.com ESMTP – VA Code Section 18.2-152.3:1 forbids use of this system for unsolicited bulk electronic mail (Spam)

      initialResponse: Elapsed time: 47 millisec
      sendingHello: EHLO RECOS02

      sendEhlo: Elapsed time: 0 millisec
      helloResponse: 250-smtp5.relay.iad3a.emailsrvr.com
250-PIPELINING
250-SIZE 75000000
250-ETRN
250-STARTTLS
250-AUTH PLAIN LOGIN
250-AUTH=PLAIN LOGIN
250-ENHANCEDSTATUSCODES
250 8BITMIME

      helloResponse: Elapsed time: 31 millisec
      login_method: LOGIN
      535 5.7.8 Error: authentication failed: UGFzc3dvcmQ6
      Failed to get response to login password
      ConnectionLog:
        220 smtp5.relay.iad3a.emailsrvr.com ESMTP – VA Code Section 18.2-152.3:1 forbids use of this system for unsolicited bulk electronic mail (Spam)
EHLO RECOS02
250-smtp5.relay.iad3a.emailsrvr.com
250-PIPELINING
250-SIZE 75000000
250-ETRN
250-STARTTLS
250-AUTH PLAIN LOGIN
250-AUTH=PLAIN LOGIN
250-ENHANCEDSTATUSCODES
250 8BITMIME
AUTH LOGIN
334 VXNlcm5hbWU6
YWNjb3VudGluZ0ByZWVzZWNvLmNvbQ==
334 UGFzc3dvcmQ6
PlVtPDJnNVo=
535 5.7.8 Error: authentication failed: UGFzc3dvcmQ6

      –ConnectionLog
      Failed to login using LOGIN method
    –SMTP_Connect
    Failed to connect to SMTP server.
    Failed.
  –VerifySmtpLogin
–ChilkatLog

What Worked To Resolve This Paperless Office Email Error

In both cases the fix was the very same. And it had nothing to do with a changed email password. For some reason we had to change one parameter in the Library Master – Company Maintenance screen.

In the field marked SMTP Encryption I changed the value from NONE to TLS/STARTTLS and then tested the email ( use the “Test E-Mail” button in the lower right corner) and found the issue was resolved.

For SMTP Encryption, the following is an explanation of the encryption each option would use between the SMTP client and SMTP server when sending e-mail.

None – Select this for no encryption. This is traditionally offered on port ID 25

SSL – Also known as Implicit SSL, select this to encrypt the communication for the entire session. This is normally offered on port ID 465

Note: SSL is a deprecated standard. It has been replaced by TLS.

TSL/Start TSL – Also known as Explicit SSL, select this to begin the communication unencrypted, then later when the client issues a STARTTLS command, communication will be encrypted for authenticating and sending the e-mail. This can be offered on a variety of ports including port ID 25, 443, or 587

Important Note: The e-mail engine used in Sage 100 2018 and Sage 100 2017 and lower use TLS 1.0. TLS (Transport Layer Security) is a cryptographic security protocol designed to provide communications security over a computer network and over the Internet. TLS 1.0 and 1.1 standards is deprecated due to known security issues. Major providers such as Apple, Google, Microsoft, Cisco, etc. have either already discontinued use in favor of current TLS 1.2 standards, or have plans to do so in the immediate future.

If the above doesn’t work – and you are using the same smtp.emailsrvr.com as the example – then try re-entering the password for the email account and test your email again.

If that still doesn’t work then you should consult your Sage partner to see if you may need to upgrade your Sage 100 to meet TLS 1.2 requirements which some email providers have been implementing.

If you found this information helpful and would like to receive timely Sage 100 news on a weekly basis – you become a member of my Sage 100 email newsletter. This newsletter goes out Thursday with tips and news related to Sage 100 ( formerly MAS 90 ).

Filed Under: Sage 100 ERP, sage 100cloud Tagged With: amyuni, email, rackspace

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