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Buy nowHello, @Drew500.
I appreciate you performing those steps to save the login credentials when emailing receipts or invoices from QuickBooks Desktop. Since it's still asking you to enter your email and password, I suggest updating your QuickBooks first. Then follow the steps MadelynC provided to start fresh.
Once completed, set up web-mail from the preferences as provided above. This way, you don't have to reenter the password when sending an email.
If that doesn't make a difference, I encourage reaching out to our Support Team to check and investigate this further.
As always, feel free to skim through our help articles in case you need related line
Keep in touch with me if you have any other questions. I'm always here to help. Have a great day!