AdobeSign sync not functional

We are integrated with AdobeSign to generate quotes, contracts, and agreements to send to customers. This is the typical flow:

1. Sales enters quote info on the Opp in SF
2. Clicks "Generate Agreement"
3. All quote info is auto-populated into our agreement template
4. Sales saves the filled agreement to the opp in SF, and sends it to customer for review and signing

However, what's currently happening is:

1. Sales enters quote info into Opp on SF
2. Clicks "Generate Agreement"
3. No data is populated, sales has to manually add all quote info
4. Sales saves agreement to computer, adds it to opp in SF, and sends it to customer for review and signing

Obviously the way it's being done now is not efficient. The sales user in question is an admin in adobe, and has all necessary permissions in SF to be able to generate quotes. There are no validation rules on the opp object that interact or interfere with AdobeSign, and there is a checkbox field labeled "Syncing" but it's greyed out and nothing we tried makes it clickable. I can't edit it to default to "checked" and it isn't a custom field, either.