as far as i know Typeform does only sync a certain number of fields. And it appears to be that your image field is not one of them. Therefore it is not syncing the files to HubSpot.
You might be able to connect Typeform and HubSpot via Zapier to also sync custom fields from Typeform to HubSpot.
Are you still experiencing this issue? If so, can you please share screenshots of where you are getting stuck and outlined what troubleshooting you have done so far?
I did want to share this resource as well which outlines what actions are available through the integration.
The more information, screenshots and details you can provide, the better the Community can assist!