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How to attach a PDF to a quote

The Prompt User outcome allows admins to require sales reps to upload a document (like a Custom MSA) before they can publish a quote. The file is appended to the quote template at generation time.

Here's how to set it up:

1. Navigate to Quote Rules

2. Create a New Rule

  • Click “Create Quote Rule”.

  • Give it a name (e.g., Attach File Rule – Enterprise MSA).

3. Set the Triggering Conditions

These determine when the rep should be prompted to upload a file.

You can use any combination of:

  • Line Items → e.g., Name contains "Enterprise"

  • Deal Properties → e.g., MSA is Redlined

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Quick Tips:

  • If you want to always require a PDF to be attached to a quote you can run a blanket rule. (e.g. If Deal Name is Known Prompt User to Attach File)
  • Otherwise you can use any combination of object properties to set the conditions for when a PDF is required. 
  • When combining multiple conditions make sure to choose the AND function on the rule builder if you want to require a PDF when all those conditions are met, otherwise use an OR function, if just one of those conditions require a user to attach a file. (if line item name is Enterprise or if customer requested a Redline, we require user to attach a file).

4. Set the Outcome to “Prompt User”

  • Scroll to the Outcome section.

  • Set the dropdown to Prompt User.

This means that when the conditions are met, the rep will be blocked from publishing the quote until they provide a PDF to be attached. 

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5. Add a Required File Upload

In the “Properties Requiring Input” section:

  • Leave the “Deal Properties” selection blank (unless you also want to require a text or dropdown field).

  • Instead, scroll to the File Description input.

  • Add the name of the required file (e.g., CUSTOM MSA).

6. Save the Rule and Turn It On

  • Click Save.

  • Make sure the rule is switched ON using the toggle (bottom right hand corner)

7. Now Generate a quote and test your rule

  • When the rule conditions have been met inside HubSpot or the quote builder your sales reps should be prompted with the following prompt. (e.g. line item name contains "Enterprise")


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They will see a section labeled “Required By Your Admin” telling them to upload a file with the label “CUSTOM MSA”.

They cannot publish the quote until a file is uploaded.

Once uploaded, the file is:

  • Stored on the quote record,

  • Appended to the final PDF output of the quote.

  • Make sure the file was successfully captured. Once succesful you will now be able to publish the quote.

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Quick Tip:

  • When the the file has been successfully uploaded, wait about 15 seconds before publishing and Preview the quote to make sure the file was attached correctly.

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