Even with that filename, I get the icon. See the attachment.
Does the problem happen in any folder? It seems that your file is on a network drive. Isn't it connected to the problem? Or do you have the problem even on local drive?
Do you see the icon correctly in Windows File Explorer in the same folder, where WinSCP fails to display it?

Hi Martin,
Sorry, I gave a different file in my reply. For the original screenshot, my file was Dell PERC H730_H730P_H830_FD33xS_FD33xD Mini_Adapter RAID Controllers firmware version 25.5.9.0001 _ Driver Details _ Dell U.pdf. I then changed the filename to this Dell PERC H730_H730P_H830_FD33xS_FD33xD Mini_Adapter RAID Controllers firmware version 25.5.9.0001.pdf and the GUI picked it up fine. Thanks.

Hi Martin,
The filename is Upgrading vCenter Server 7.0 fails during precheck with _Host(s) were found in the vCenter Inventory, that are potentially problematic for a vCenter upgrade_ (86447).pdf. And I've tried both 6.1.2 and 6.2.2 beta versions.

Thanks for your report.
How long is the filename? How long is the complete path? What version of WinSCP are you using? Did you try the beta version?

Hello,
I have a pdf file with a little long name and in the GUI left pane, the Type is not showing it as a pdf file. Is it related to Issue 2242 – Cannot browse long local paths. Thank you.