Email authentication error when sending invoices via email

Hello there, @Bruuske.

Thank you for posting in the Community. Allow me to help share some ways to make sure you're able to send invoices in QuickBooks.

To start, let's check the system requirements to make sure your email account is compatible with your QuickBooks version. For more information about the system requirements, you can visit this article: QuickBooks for Mac 2019.

After that, let's make sure to use your Gmail account as the default email. QuickBooks sends the emails, with invoices attached as PDF forms, from your business email account.

To do that, let's check this on your email preferences. Let me show you how:

1. Choose Apple Mail.
2. Select Preferences.
3. On the Preferences pane, click General.
4. Confirm the email is your default email account. 

If the default email is not your Gmail account, I recommend reaching out to the Apple support to change it. This way, you can use the correct email when sending invoices in QuickBooks Mac. 

I've also attached an article for additional reference: QuickBooks Desktop for Mac 2019 User's Guide (page 228).

If you need to reach out for more help, I also suggest calling our phone agents. They have the tools that can help you get this resolved in no time. 

Here's how you can reach them: 

1. Go to: https://help.quickbooks.intuit.com/en_US/contact.
2. At the top right, select your product.
3. Choose your QuickBooks version.
4. Select a topic.
5. Click on the Get Phone Number button.

That should point you in the right direction today. I'm just a post away if you have any other questions about sending an invoice. I'll be happy to help you out. Wishing you and your business success. 

Hi @MaryGraceS 

Thanks for your quick reply to my issue. I'm not using the desktop client email on my Mac. I'm using the built-in smtp set-up in quickbooks. See the attached screenshot (replaced my info with fake info). What's interesting is this same set-up worked before the latest update of QB and when I hit OK with my real info in the fields it says it has authenticated properly and it worked. When I go to send the emails from the invoice screen, I get the error message that is attached to my first message.

Best, 

Chris

Hi @Anonymous 

I called tech support and they worked on the issue for about an hour and couldn't resolve it. It looks like setting up QB to email directly via SMTP with a Gmail account is not working for the 2019 Mac version at this time. She told me to contact Google to try to resolve it, but I don't think it's an issue on their end. I'm going to just use the default mail client on my Mac as a workaround until the custom email issue is resolved.

Cheers,

Chris

Hi LilyC,

I've just upgrading to QBM 2019, and I have essentially the same problem, except that I don't use 2FA or tokens, so this shouldn't be an issue; additionally I've tried several email accounts hosted by different providers/servers. I can verify that all my settings are correct, and that the Email area where the account is entered both tests and verifies the accounts as working and able to connect.

I'm very curious about what you mean by, "You can create another profile to check if you still get the same error message."

Do you mean essentially what I've already done, i.e., create new/different Email account profiles in the same pane, or is there another Profiles feature I'm not aware of or that isn't directly related to Email?

Thanks in advance for clarifying this suggestion.

Frederico 

Hi, MikiD, thanks for the response.

I should have been more explicit, and less implicit; in testing numerous email accounts, including gmail, none have 2FA, and gmail was already set for 'Less Secure'.

Thanks, but the bug is real, needs to be addressed by engineers, and I have another thread that goes into precise details.

Happy Thursday

Thanks for providing feedback, Frederico.

To create an investigation ticket, we need you to get in touch with our Customer Care hotline. The form needs the affected user's credential information, and the steps tried for the email authentication error. That way, they can start further investigation according to the data gathered.

Since Community is a public forum, we don't encourage customers to post their personal details here. To secure your private data, follow the steps below on how to reach out to our one-on-one interaction support.

1. Visit this link: https://help.quickbooks.intuit.com/en_US/contactus.
2. Select QuickBooks Mac Desktop.
3. Select the issue/topic.
4. Click the Get Phone Number button to see the support number.

Keep me posted on how it goes or there's anything else you need about QB Mac. I'm always here to offer my assistance. Have a good one.

This is the second time this has happened to me.  

Thanks for joining this thread, @kenjohn. I'm here to help you get your invoices sent via email.

The error message you're having implies that the username and password set in your Preferences aren't matching the sign-in info of your email address. I recommend ensuring your login info for your email is correct. 

Here's how:

1. Go to the QuickBooks menu, then Preferences.
2. Click the Email icon.
3. From Send Emails Using, hit Custom.
4. A list of email accounts will appear. If you haven't added any email accounts to QuickBooks, this list will be empty.
5. Select the + button to add a new account.
6. Add an account name, then add the settings from your email provider.
7. Repeat for any other accounts you’d like to add.

Then, make sure your Gmail account is the default email reader from the Apple Mail menu. Doing this ensures the program sends your sales forms through the default email account. 

1. Select Apple Mail.
2. Choose Preferences.
3. On the Preferences pane, click General.
4. Confirm Gmail is your default email account. If not, set your default email reader to Gmail. 

Additionally, you can go back to your Preferences to make sure Gmail is your default email reader by performing the steps below.

1. Go to QuickBooks from the top menu.
2. Select Preferences.
3. Click the Email icon.
4. Configure QuickBooks to talk to Gmail.

Once done, try sending your email again.

1. Open the form you'd want to send.
2. Click the Email button at the top of the form. Here you can: 
   • Choose the default message text 
   • Customize the subject 
   • Choose the sending email address
     
3.  Click Send.

For detailed steps, see page 228 through this website: QuickBooks for Mac. 

Visit me here again in the Community and keep me posted on your progress with this authentication error. I'm determined to help you succeed.

I have the same issue too. We have been using our email with QB for years and then one day it just stopped working with the same errors as you and I can't fix it.

I know this hasn't been an easy process for you, erinloewy.

I'm here to make sure you'll be able to send invoices again. If you're done following the troubleshooting steps, I'd suggest reaching out to them to determine the main cause of this. They can also further check and have this investigated.

Here's how you can reach them: 

1. Go to: https://help.quickbooks.intuit.com/en_US/contact.
2. At the top right, select your product.
3. Choose your QuickBooks version.
4. Click Search for something else. 
5. Enter your concern in the Ask us anything field, then choose Search.
6. Once done, click on Start a Message.

Additionally, I've included our QuickBooks Desktop for Mac 2019 User's Guide. This contains articles that'll help you in achieving your future task.

In case you'll need assistance in dealing with QuickBooks transactions, don't hesitate to get back to this thread. We're always here to help you.