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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 ).

Sage 100 2018 Paperless Email Delivery Problems?

November 1, 2021 by Wayne Schulz

Sage 100 version 2018 users may experience problems sending email forms such as invoices or statements through Paperless Office. This issue can be sporadic or it may cause a complete shutdown of email delivery. The root cause is the lack of support for TLS 1.2+ by the 2018 ( and earlier ) versions of Sage 100.

Sage 100 v2018 uses TLS 1.0 which is an outdated protocol no longer accepted by many email providers. Versions 2019 and higher of Sage 100 provide support for TLS 1.2 and therefore won’t experience this type of error.

On November 3, 2021, Sage released a patch for Sage 100 version 2018.x which enables the use of TLS 1.2 when communicating with email servers.

Sample Sage 100 Paperless Delivery Error Message

If your email delivery fails you due to incompatible TLS levels you will see the following as part of your error message.

Connection closed by server.
Failed to read beginning of SSL/TLS record.
Failed to read incoming handshake messages. (1)
Client handshake failed.
Failed to establish TLS connection.
–SMTP_Connect
Failed to connect to SMTP server.
Failed.
–VerifySmtpLogin
–ChilkatLog

How Can I Fix Sage 100 Paperless Email Delivery Issues?

The most complete way to resolve Paperless Office email delivery issues with Sage 100 2018 is to update to Sage 100 v2021 which includes both TLS 1.2 support as well as OAuth (Open Authorization): This new option ( available for subscription versions of Sage 100 only ) is an open standard authorization protocol used to grant access using access tokens instead of sharing a user name and password.

Update – Sage released LM6026T on 11-3-2021. It may resolve this issue for those users on Sage 100 2018 as it adds the ability to use TLS 1.2 with email servers.

What If We Can’t Upgrade Sage 100 Right Away?

If you cannot upgrade your Sage 100 to the latest release there are several options available to restore the ability of your Sage 100 v2018 email capabilities.

SMTP2GO – External SMTP Email Server

The easiest way to resolve this issue is by using a third-party SMTP service like smtp2go. These types of services charge a fee for the flexibility of configuring their SMTP server to accept external email and many won’t require a specific level of TLS.

With an external SMTP server, you’ll swap in the external server’s address and configure Sage 100 to send all email

SMTP Relay Using An Office 365 Connector

SMTP relay lets Microsoft 365 or Office 365 relay emails on your behalf by using a connector that’s configured with your public IP address or a TLS certificate.

Follow these instructions to create an SMTP relay if you are using Office 365.

Wait For A Sage Patch for Sage 100 2018

Sage has indicated they are working on a patch for Sage 100 2018. This is likely the only version that will receive a patch and even with the patch to allow for TLS 1.2 compatibility the version 2018 release still lacks OAuth which may soon be required to connect an email to Microsoft Office 365.

The issue that many on older versions of Sage 100 have experienced underscores the importance of remaining current on Sage 100. If you have not updated we recommend doing so as soon as practical and adopting version 2021 or higher for maximum compatibility with future technology.

Sage 100 Paperless with Gmail and Less Secure Apps

November 17, 2020 by Wayne Schulz

We just ran across an instance where a customer using Sage 100 2020.x and paperless office for electronic delivery of statements was suddenly having their Google Workspace ( aka G-Suite or Gmail ) email account login and password rejected.

It’s important to note that this customer was NOT using two-factor authentication with Google. If they were to use two-factor this issue likely would have been resolved by using an app-specific password ( only available to those with two-factor enabled).

Just one month ago we thought we’d resolved this issue by enabling less secure applications within their Google email.

Google has begun tightening their security protocols for what they term less secure apps. Essentially these are apps which require you to enter in your Google credentials as opposed to using a more secure authentication which might grant access to only a portion of your Google account such as only email or only calendar access.

You can read more about Google’s less secure apps policy here.

It appears that while you can enable access for less secure apps, Google will periodically disable that access should the app not login for an undefined period of time.

This is apparently what was happening as our customer only printed statements every 30 days.

The resolution to the rejected login from within Sage 100 paperless office was to once again enable less secure apps from the Google account.

Email Scam Warning: Beware Of Friends Claiming To Be Trapped Overseas Needing Quick Money

October 10, 2012 by Wayne Schulz

This morning I awoke to the email below in my inbox. I immediately suspected that it was a scam because:

It was from someone who I did not know well enough to be asking me for money
The person claimed that their credit cards were stolen and they were being told by the hotel that they must settle their room charges before departing. Now I don’t know about you but it’s been a good 10 to 20 years since I’ve been to a hotel where they did not keep my credit card on file. In many cases the charges are even prepaid.

How does this scam work?

Someone’s email account is hacked – usually by tricking them into a bogus (but official looking) site that prompts them to enter their user name and password for their email account. This is quite often done in “pfishing” emails that seem valid but their intent is to steal your user name and password.

Once the email login and password has been stolen the hacker has full access to send out emails to anyone in the address book. Since these contacts likely know each other it’s far more likely that a hack of this type might work on at least one or two unsuspecting friends.

Here’s The Email That Was Sent

From: xxxxxx
Date: Wed, Oct 10, 2012 at 7:24 AM
Subject: Awful Ordeal……xxxxxx (friend’s name)
To: Undisclosed recipients

Hello,

This message may be coming to you as a surprise but I need your help. Few days back we made an unannounced vacation trip to London, United Kingdom. Everything was going fine until last night when we got mugged on our way back to the hotel, all cash and credit card were stolen off us but luckily for us we still have our passports with us.

I’ve been to the Embassy and the Police here but they’re not helping issues at all they asked us to wait for 3 weeks but we can’t wait till then and our flight leaves in few hours from now but we’re having problems settling the hotel bills and the hotel manager won’t let us leave until we settle the hotel bills, Dealing with foreign authorities here is extremely frustrating, It would take us about 24 hours to get everything straighten out before we could leave, we are freaked out at the moment…I really need your financial assistance.

Please let me know if you could help us out financially?

What The Scammer Hopes Happens

The scam relies on you knowing the person who sent the email. They hope you will reply back (remember the scammer is in control of the email account) and at that point you’ll likely be given instructions to wire transfer funds urgently overseas.

If you do transfer funds – expect that will be the last you ever see of the money.

Your best bet is to contact your friend immediately by phone (do not reply to the compromised email) and verify the information.