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Hello there, joe.
I appreciate the steps you've performed and the details you shared. The option that allows you to enter 10,000 characters in the estimate or an attachment to a template is currently unavailable. I can see how crucial it is to make running your business easier. I'll ensure you can send feedback so this suggestion is forwarded to the Product Development Team.
I recommend submitting feedback on the ability to have more than 4000 characters or add an attachment to the estimate template. The recommendations are sent to our engineer for consideration in future updates.
Here's how:
On the other hand, please know that when duplicating an estimate, the attachment will also automatically be included. Since this doesn't happen on your end, I recommend logging into QBO using a private/incognito browser. Then, duplicate the transaction from there. This is to rule out any webpage issues, as incognito mode doesn't store local files or cache.
Use these keyboard shortcuts based on the browser you're using:
If it works in incognito, you'll need to clear the cache of your regular browser. It deletes the history or log of sites so you can start with a clean slate. If the steps above don't work, use another supported browser as an alternative.
In case you need steps on how you can view all created estimates and their status at a glance, you can read this article: View sales transactions in QuickBooks Online.
Please don't hesitate to come back again if you need further help with your estimates or any QuickBooks-related concerns. We'd be more than happy to assist you 24/7, joe. Take care!