Every time I email an invoice, your crappy software asks me for my yahoo password, some odd 16 character mess. Why doesn't your crappy sofware save the password?

Hey there, @MarkWantsBetterCS.

For users with sensitive information, setting a password is mandatory. It ensures that only authorized users can access your data.

You can set up webmail to work with QuickBooks. This way, you don’t have to reenter your password every time you send an email.

Here’s how:

1. Go the Edit menu and choose Preferences.
2. Select Send Forms.
3. Click Webmail and Add.
4. Fill out the Add Email Info and select OK.
5. Select OK to save your changes.

To get more about setting up an email, please visit this article: Connect your email to QuickBooks Desktop.

Moving forward, you can create and use customize email templates to send messages.

You can always get back to me if you need more help in setting up your email in QuickBooks. I'll be around to help.

I'm encountering the same issue.  Once I've created an invoice then will send the invoice by email to the customer, QB2018 asks me to enter my password for my email account.  Then it says that if I run Schedule Reports, the password will be saved.  I did not see that option under Schedule Reports. 

Do I have to enter the email password every time I send an invoice?

I recently have been having the same issue sending emails through QB via, Outlook via, Yahoo .

I've been receiving notifications from Yahoo about using their app on my phone but have ignored them until today as after reading the email, the same notice applies to my Desktop as well because I use Outlook. I would think that you would of received the same notifications as me.

I manage multiple emails on my Desktop PC using Outlook as I manage multiple companies in QB. I reset the Yahoo password in Outlook and in QB per Yahoo's instructions below.

IN YAHOO go to:

Some older, third-party email apps (that do not use our Yahoo branded sign in page) require you to enter a single password for login credentials. To access your Yahoo Mail account on these apps, you'll need to generate and use an app password. An app password is a long, randomly generated code that gives a non-Yahoo app permission to access your Yahoo account. You’ll only need to provide this code once to sign in to your third-party email app.

Generate an app password

Using the instructions above initially resolved my issue but I later discovered for it to work without interruption, having to enter the secure password when I sign out and back in, my Yahoo email must be listed in Outlook as my default email account, which I have not done as it is not my primary email address. Unfortunately for me I will always have to renter my password in order to send emails through QB. If you only use Yahoo as your email provider then these instructions should resolve any issues you have sending emails through QB.

Hope this helps!!

I'm not a QB rep - just another qbuser but after finding no help from QB, I fixed this problem this way (Desktop QB version): Open Company preferences (Edit tab on the task bar and last option "preferences".)  When the box opens, find from the menu on the left, the "General" tab and open it.  Then choose "Company Preferences".   Find "Manage login settings" middle of box and choose "Keep user logged in for _____ , and choose the option you want.  

Next, go back to the tab, "Service Connection" on the left menu. (QB may ask if you want to save your changes at this point. Choose "yes" (obviously). 

Under Company Preferences again, choose "Automatically connect without using a password."  

This solution assumes that you have already properly set up your email account for use by QB, which requires you to make certain changes within your email service provider security protocols, e.g., Googe requires you to turn on "allow less secure apps" in your preferences before you can send email via qb.  That's a different issue and QB actually does have a step by step help answer to get you through that.

I hope this helps some of you.   

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.