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Experienced Member

Error Sending Email with Quickbooks for Mac 2019: 5.7.8 Error: authentication failed (error message in error)

Greetings,

 

Quickbooks for Mac 2019 offers two options for sending invoices/statements in Preferences -> Email; one is to use the clunky, but functioning, method of generating invoices and a cover letter using Apple Mail; the other is to use the integrated emailer directly inside Quickbooks, as also exists and works on Windows.

 

I have tested six different email accounts with the integrated function, from private servers using different hosts, as well as testing with gmail (the largest email provider on the planet), and all validate properly during setup: the edit window shows 'Testing Connection… ' and then closes itself to the main Email panel; ergo, the absence of an error message indicates success.

 

The logs further reflect this successful test with code:0 (zero errors).

 

This proves that the username/password/ports/authentication-type/etc are all correct, or else it would timeout or produce an error. Indeed, if I intentionally enter the wrong information, or choose the wrong connection parameter, an error message indicating the same bad information to be at fault appears swiftly; the logs then indicate codes ranging from 1-9, depending on what I intentionally set incorrectly.

 

Once I enter information correctly, and the test is validated, when I go to test actually sending an invoice or statement, QB quickly returns the exact same error with every account of every type: 

 

Unable to authenticate with the current session's credentials.

The server returned the response: 5.7.8 Error: authentication failed: 

 

(notice the empty colon ':" ; the engineers failed to even allow for a complete error message)

 

The logs then actually report two separate errors:

 

19/05/23 03:00:50.613: {emailer} Error setting up SMTP: Error Domain=MCOErrorDomain Code=1 "A stable connection to the server could not be established." UserInfo={NSLocalizedDescription=A stable connection to the server could not be established.


19/05/23 03:02:49.635: {emailer} Error sending email: Error Domain=MCOErrorDomain Code=5 "Unable to authenticate with the current session's credentials." UserInfo={MCOSMTPResponseCodeKey=535, NSLocalizedDescription=Unable to authenticate with the current session's credentials., MCOSMTPResponseKey=5.7.8 Error: authentication failed:
}

 

The second one claims that my username/password are incorrect, however, we know that not to be the case (see above); it is the first error ("A stable connection to the server could not be established.") that is likely at the root of this problem.

 

Before you ask, no, none of these accounts use 2FA; gmail is properly set for 'Allow Less Secure Access', etc.; the settings entered in QB are identical to the settings in macOS Apple Mail, and a dozen other devices using these accounts with other third party applications and utilities that allow for custom (self-owned) email accounts from within said app.

 

The same gmail account works with QB Pro 2016 Windows, and previously worked in earlier versions of QB Mac.

 

This is a major bug in an advertised feature selling on a $300/seat application; I think it reasonable it be expected to actually work. I had to spend a considerable amount of time with support, both arguing and demonstrating via screen sharing, as well as on hold, transferred to a supervisor, etc., in order to convince them of the same and give me a trouble ticket with a promise to escalate to engineering.

 

And, again, just using the clunky, slow process of passing the ball off to Apple Mail using the obviously-AppleScript method isn't acceptable; if I'm going to batch send a few hundred statements, I'm not okay with not being able to use Mail myself while I'm waiting, especially if a bunch of statements throw errors (e.g., missing email address); nor is it particularly enjoyable watching all the window opening/flashing even when it works "smoothly".

 

If anyone has any solutions -- again, not workarounds using Apple Mail -- I'd very much appreciate your information. If and when engineering gets back to me, I will update; similarly, if this is bound to be wrapped in a bug fix, I will likewise update. However, that latter outcome is likely months and months away, at best, if the QB Mac release history in past years is any indication.

 

Happy Wednesday

 

Frederico 

 

 

 

 

 

 

 

 

 

 

8 Comments
QuickBooks Team

Re: Error Sending Email with Quickbooks for Mac 2019: 5.7.8 Error: authentication failed (error m...

Thanks for providing detailed information, Frederico. 

 

I suggest updating your QuickBooks Desktop to improve program functionality and fix software issues: Update QuickBooks Mac Desktop.

 

Also, I recommend reaching out to our customer support team again for updates and resolution. 

 

Always know the Community is always around if you need more help. 

Experienced Member

Re: Error Sending Email with Quickbooks for Mac 2019: 5.7.8 Error: authentication failed (error m...

Thanks for the suggestion, Catherine.

 

QB Update Reports:

 

You’re up-to-date!

QuickBooks 18.0.5.3312 R6 is currently the newest version available.

 

The link you provided links to another page which appears to be dead (at least it refuses to load for the last ten minutes).

 

Are you saying there is a newer release available than the one I just downloaded last week?

 

TIA

 

QuickBooks Team

Re: Error Sending Email with Quickbooks for Mac 2019: 5.7.8 Error: authentication failed (error m...

Our system updates time to time to provided fixes, Frederico.

 

Since your QuickBooks Desktop for Mac is already up-to-date, I'd recommend contacting our Customer Care team again. They have the tools that can pull up your company file in a secure environment. Also, they can help you further in resolving this concern.

 

Let me know how it goes by leaving a comment below.

Experienced Member

Re: Error Sending Email with Quickbooks for Mac 2019: 5.7.8 Error: authentication failed (error m...

At this point I'm waiting for your team to return a promised call back; but I keep hoping another member or community participant has seen this and knows the answer.

 

Several threads on this forum and elsewhere describe the *exact* same problem, however, the solution nearly always offered is to just use Apple Mail and ignore the broken feature.

 

It appears as though this SMTP bug comes and goes with update releases, and the fix doesn't always hold. Even for those gmail users who manage to get 2FA working with an app token, it doesn't last.

 

Regardless, I need to use my own company domain, not hosted by gmail or Intuit.

 

Kind Regards

 

Frederico 

 

Experienced Member

Re: Error Sending Email with Quickbooks for Mac 2019: 5.7.8 Error: authentication failed (error m...

At this point I'm waiting for your team to return a promised call back; but I keep hoping another member or community participant has seen this and knows the answer.

 

Several threads on this forum and elsewhere describe the *exact* same problem, however, the solution nearly always offered is to just use Apple Mail and ignore the broken feature.

 

It appears as though this SMTP bug comes and goes with update releases, and the fix doesn't always hold. Even for those gmail users who manage to get 2FA working with an app token, it doesn't last.

 

Regardless, I need to use my own company domain, not hosted by gmail or Intuit.

 

Kind Regards

 

Frederico 

 

 

QuickBooks Team

Re: Error Sending Email with Quickbooks for Mac 2019: 5.7.8 Error: authentication failed (error m...

Hello there, @Frederico,

 

I see you've already contacted our support team to report your email concern. I'm here to point you in the right direction. 

 

Since you want to use your company domain, I’d suggest consulting your email provider to see if they support the sending of forms functionality in the program. If supported, they can also help fix the authentication error.

 

You can also download this helpful guide and refer to the page 230 on how to troubleshoot it: QuickBooks Desktop for Mac 2019 User’s Guide

 

Keep in touch with me how it goes after contacting your email provider, @Frederico

 

I'll be here if you need further help. Have a great day. 

 

Thanks,

 

Raymond

Experienced Member

Re: Error Sending Email with Quickbooks for Mac 2019: 5.7.8 Error: authentication failed (error m...

Hi Raymond, than you for your suggestions.

 

First, the help you suggest actually begins on page 226-228 of the linked document (for others reading this thread); second, it again only discusses in general details the options for using third party email clients to send email. As stated quite clearly in my OP, I do not want to use the third party option; I want to use the integrated SMTP feature built-in to QB 2019 for Mac. I can find absolutely no mention of this integrated "emailer" feature in the linked document, let alone instructions on how to set it up or troubleshoot it.

 

As far as my compnay domain, I know for a fact it supports what I need, because we also do it from Quickbooks Pro 2016 for Windows, and it works fine.

 

Additionally, the integrated emailer feature as of this writing, doesn't even work with gmail, the largest provider on the planet; there are a number of threads on this forum making the same complaint as I have.

 

I have filed a trouble ticket, and I'm awaiting a return call. Again, I keep hoping someone who has both experienced this same issue/bug/broken feature and has actually read my post to know I *DO NOT WANT* to use third party email will offer up their discovered solution, or at least commiserate with "me too" so as to make engineering understand this bug is affecting more than just me and needs to be fixed.

 

Thanks

 

Frederico 

 

 

 

Established Community Backer ***

Re: Error Sending Email with Quickbooks for Mac 2019: 5.7.8 Error: authentication failed (error m...

I'm on the engineering team. Obviously this feature worked in our testing or we would not have shipped it. Email configuration being as varied as it is the likelihood is that something particular about your configuration is causing the issue. To fix it we'll need to reproduce your configuration. 

 

Please send me an email at qbmacforum1 @ intuit.com  (remove the extra spaces I put in to allow this to post) and include the url to this discussion in the body. I'll reply to try and get information from you to duplicate your configuration and reproduce the issue - including the truncated error message. 

 

I work directly with QA and engineering on QuickBooks Mac.