Hi, ciccioesse!
How are you?
Are you using our last version?
Would you please the form tags (maybe in pastebin)?
We process and save the uploaded files with wp_unique_filename function to avoid overwriting (that’s why the second Schermata become Schermata-1 and so on). I tested here indeed and the problem did not happen.
Are you using any other plugin for CF7? Maybe it’s a conflict case.
My form:
[file file-example]
[file file-example2]
My files:

Thanks for answer,
I use CF7 Version 5.1.4 with CF7 to Webhook Version 2.2.3.
Yes I use some other CF7 extension, I can try to disable, but I think this isn’t the problem.
This is my form:
<label> Driving Licence Front Picture (Mandatory)
[file file-dl-front limit:5242880 filetypes:jpeg|jpg|pdf|png]</label>
<label> Driving Licence Rear Picture (Mandatory)
[file file-dl-rear limit:5242880 filetypes:jpeg|jpg|pdf|png]</label>
<label> CBT (if needed)
[file file-cbt limit:5242880 filetypes:jpeg|jpg|pdf|png]</label>
<label> DVLA Code PDF (Mandatory)
[file file-dval limit:5242880 filetypes:jpeg|jpg|pdf|png]</label>
<label> National Insurance Picture
[file file-nti limit:5242880 filetypes:jpeg|jpg|pdf|png]</label>
<label> Proof of Address (Mandatory only for independent riders, not for companies)
[file file-proof-address limit:5242880 filetypes:jpeg|jpg|pdf|png]</label>
<label> Screenshot of profile in rider app (Deliveroo, UberEats, Stuart, Ryders etc only for indipendent rider, not for companies)
[file file-screenshot limit:5242880 filetypes:jpeg|jpg|pdf|png]</label>
Hi. Did you try disabling other plugins?