Has this been fixed yet? I have a customer with Outlook issues. Turns out I had to create an app password for their Outlook, I don't know how they were using it before. They started also stating they used to send invoices easier before in QB, so I mentioned you can do it in QuickBooks. Because I just helped a customer with QuickBooks for Mac and I believe their QB didn't ask for a password every time they sent an invoice within the program.

I thought QB Desktop would be the same, so I told the customer I can make it happen. I made it happen once, but then tried again and it kept asking for the password. That dang Yahoo app password is 16 random characters long!

No way I'm telling them to cut and paste their password every time to try an make their lives easier. If this hasn't been fixed in any recent updates, I suppose they'll just have to suffer using Outlook as an external invoice emailer. It just sucks because Outlook has to slowly load up just to send it, computer still has a spinning hard drive.

The one time it worked within QB was nice and fast! Oh well, I'll just have to tell my customer QuickBooks cannot send invoices within the program because the programmers lack the knowledge to store encrypted salted hash passwords.

Same problem, but it started following the installation of the latest QB upgrade. Using Office365 and for 2 years I have been sending out Invoices and Purchase Orders etc. without the need to enter a password, and now I get prompted to enter a password. Spent hours on a call with Quickbooks Support basically doing what is on this thread + re-upgrading QuickBooks, upgrading Office365 etc.

It seems that the problem is when you try checking the  "Use enhanced security" box the default server for Outlook/Hotmail/Live is 'smtp.live.com' but it should be 'smtp.office365.com'. (Using Office365  throws off email error messages until you make the server change in Preferences. However, when you check the "security" box you can no longer get any Office365 email to pass the webmail authorization process and you end up getting an XML error message in a QB Webmail Authorization box.

Support has no idea

I think I may have this issue partially addressed, but going to spell it out just to make sure we're all on the same page.

Problem: When trying to email invoices, it asks for password. Entering my email password fails. By getting a "Secure Mail Key" from ATT/Yahoo/SBCGlobal or "App Specific Password" from other companies, I'm given a 16 alphanumeric code instead. When putting that in, it works to send emails again, but once QB is closed, and reopened, it asks for the password again.

This is not a solution, but rather a "We understand the problem and have a workaround"

Quickbooks, in order to use the "App Specific Password" or "Secure Mail Key" needs to have the "Use Enhanced Security" option turned on in the Preferences > Send Forms > Edit section of email. However, as of some time mid-2020, this feature is missing/broken. QB has indicated they're aware of the issue, and have BEEN aware for almost a year, and not fixed it. 

That said, there are two workarounds.

1) Keep your App Specific Password in a text file on your desktop, and copy and paste it every time it asks (once a day?). This is both obnoxious, and a security concern, but still a viable option.

2) Send invoices from a different email that doesn't use an App Specific Password. Best recommendation is to use a Gmail account, and turn on the feature called "Less Secure Apps". It functions in the same method but simply 'allows stuff' rather than create a new password. This is a similar process for using Gmail on Outlook for desktop.

I'm under the impression that QB simply isn't going to fix this until a proper amount of ire is raised, which may be never, since finding solutions and even identifying the problem is a project in itself. 

SAME! So frustrating! Always just logged in using my password for my yahoo mail. Now I have to go into my yahoo mail account settings and have it generate a new password. Will only email 12 invoices before I have to go back in and generate a new password! Also can’t email from my printer anymore, same issue. Because it’s set up to my yahoo password also. All this happened since the last QB update! 

Mine is not working any more, the SECURE EMAIL setting in google is now saying APP IS BLOCKED. I'm using Gsuite.

the only way I can send invoices now is to uncheck the SECURE EMAIL checkbox, but then I have to enter in my password every time.

COMPLETE GARBAGE!

Mine is not working any more, the SECURE EMAIL setting in google is now saying APP IS BLOCKED. I'm using Gsuite.

the only way I can send invoices now is to uncheck the SECURE EMAIL checkbox, but then I have to enter in my password every time.

COMPLETE GARBAGE!

I have tried signing in as you stated, but I get an error saying your server is unavailable, try again later. Grrr. It wasn't always this complicated. Never had these issues when I first purchased Quickbooks a few years ago. Now it so time consuming to get a simple task done. We are trying to work here. It's incredibly frustrating when you have a long to-do list, but have to waste a bunch of time on something that should be and once was so simple. Time is money!!

Unfortunately for me, there wasn't any login settings under general company preferences or my preferences for that matter.

Still no fix and unfortunately that ridiculous password needs to be entered every time they will want to email anything. I recommend getting them a better program. QB used to be great, but like everything else these days it seems to be getting more and more dysfunctional with every "new and improved version". Do you happen to know of any other programs that actually work well for company financial management? I've had it with QB!

I'm sure Yahoo is partially responsible for this mess. But getting any help from them I'm guessing will be just as pointless as it has been here. These companies and their fake customer support. It is literally impossible to get good customer service anymore. Grrr.

If you have Avast antivirus, try disabling the mail shield for SMTP messages. 

If you have Avast Antivirus, or something similar, try disabling the Mail Shield scan for SMTP messages.

I see LOTS of people with this problem, but NO solutions.  This is NOT acceptable.

It's been years.  I just contacted intuit support by phone.  They ran through their script and the useless customer service rep couldn't figure out anything different.  Then the cs rep refused to transfer me to a supervisor and then told me they can't get a supervisor to call me back.  I spent over 30 minutes replicating the invoice email procedure just to appease the idiotic customer service rep that has to follow a script.

What a waste of time.

Intuit customer service is the worst.  The reps follow a script, and blame anything but quickbooks if it doesn't go according to their script.  And without an escalation path, any major complaint get dropped right there.

Intuit customer service is horrible.

Nothing to do with that at all.  I don't think you read the issue or understand it.

Yahoo has nothing to do with this issue.  Any email system providing 3rd party access will have the same issue.

The Issue is simply that Intuit doesn't care to fix the product.

Disable your antivirus' mail-shield or mail-scanner. I had three clients with this exact issue and it worked for all three. Won't hurt to try it!

I was able to solve this by adding a default email account to my Windows 10 profile. Forgive my instructions, I'm not a formerly trained tech guy, I just like to solve problems.

1) Windows Start menu.

2) On the left side of the drop down from bottom to top will be icons for power, settings, pictures, documents, and your user account/profile.

3) Select the user account icon and then select "change account settings" in the pop up.

4) Select "Email & accounts."

5) Select "Add an Account"

6) Add in your email account and password just as it is in your email program. 

7) Hint: I use Outlook 365 for my Gmail account on multiple PCs, so I selected the "IMAP" option.

Hope this helps. As I said, I'm no expert, I just stumbled across this solution while trying to solve this problem.

The generate app password feature for Yahoo is broken, with an unknown ETA for it to be fixed. Is there a work around for this scenario? 

Hello there, queen. I know how important this feature be fixed as soon as possible and your patience will be highly appreciated. I'm here to help you. 

I've checked our resources and verified there are open cases related to your Yahoo concern. If you've already tried the suggested troubleshooting steps provided by my colleagues above.

I'd suggest reaching out to our QuickBooks Desktop Support Team. This way, they can securely look into your account setup and provide a workaround. Also, they can investigate further about the issue since there are already open cases with generating passwords feature for Yahoo. Here's how:
 

1. Click Help at the top menu bar, then select QuickBooks Desktop Help.
2. Select Contact us and then enter that you get Reminder prompts and Continue.
3. Then choose either to Message an Agent or Talk to a Specialist.
    

Please check out this article for QuickBooks support hours: Contact QuickBooks Desktop Support.

You may also refer to the following articles on how to manage your email services and fix your password concerns:
 

• Connect your email to QuickBooks Desktop
• Fix webmail password issues in QuickBooks Desktop
   

If you have any other QuickBooks-related concerns. I'll be around. Have a good one!

How ill informed quickbook employees are. It took non intuit years to reply to this post.  Then they reply with false and misleading information.  There are no workarounds.  This bug hasn't been fixed in years.  And your company again takes no action. Takes no accountability.  Blames users for your company mistakes.  If you call in regarding this bug you have to walk through some junior rep's script. Then the rep will say there is no bug. Also they won't escalate the issue.  Continue burying your head on the sand and further creating more customer service issues.  Definitely Not a helpful nor valid reply!

Good to know if not just me.  Thought about upgrading to newest version of QB but see that won't help.  Want to stay in the loop to see if anyone gets a fix.

Glad it's not just me.  So irritating.  Was thinking of upgrading QB to a newer version but I see that won't help.  Please keep me in the loop.

 I hear your sentiments and I can see how difficult it is not to be able to send invoices properly in QuickBooks. I want to ensure this will be taken care of.

If you have already performed the steps provided in this thread and still experiencing the issue, I highly recommend reaching out to our Technical Support team. They'll be able to further investigate the root cause of the issue and provide additional steps to fix this. Once connected, you can also request a screen-sharing session so they can check your setup. Let me guide you on how:

1. Open your QuickBooks company file and go to Help, then select QuickBooks Desktop Help.
2. Next, select Contact Us.
3. Enter a brief description of your issue and select Continue.
4. Log in to your Intuit account and select Continue and then Continue with my account.
5. You'll receive a single-use code. Enter it and select Continue.
6. Choose either Chat with us or Have us call you.

To ensure you'll get assisted immediately, feel free to visit our support hours page.

In the meantime, you can refer to the workaround provided by @jnmccool1 to resolve the password prompt when emailing invoices in QuickBooks. 

QuickBooks also makes it easy to modify the email templates to make them more personalized when sending them to your customers or vendors. For the detailed instructions, please read this article: Create custom email templates in QuickBooks Desktop.

If you have any other concerns managing invoices in QuickBooks. Don't hesitate to post a reply below. Have a good one.