Hi rileyvenne,
Welcome to Community! It's essential that your QuickBooks Online estimates are complete, when sending them to your customers. Missing attachments is concerning. I would be happy to help!
I recommend turning on, Microsoft XPS Document Writer. Here's how;
1. Press Windows + R and type appwiz.cpl in the Run window.
2. Press Enter, and from the left side panel, click Turn Windows features on or off
3. See if the checkbox beside the Microsoft XPS Document Writer is marked and if not, then select the box.
Should you require additional assistance, please don't hesitate to contact us, outside of this forum. They'll be able to look into your situation in more depth and escalate it for further investigation if necessary.
If you have any other questions, feel free to reach back out. We would be happy to help!