Problem With Cross-Platform Skype

[ameerat42]

The scene:
I have Win 10 and the latest version of Skype for it.
A contact has the latest Mac version of Skype on his Mac.
Everything works as far as normal calls/video/Instant Messaging go...

But:
Try to send a file (usually an image) the way you USUALLY do in Skype, and...
He gets a link to click on, and there he has to sign in again to receive the file
(at least we think so, as we haven't bovvered to do so).

And then:
If he logs into the Windows (7) version of Skype that he has, there is NO SUCH PROBLEM/Step
involved in sending and receiving the file. It just downloads in his open session of Skype.

Qs:
Have other people found this when communicating cross-platform using Skype?
Is there a simple solution (like use Yahoo Messenger instead)?
Do you find it is "Improving your Skype Experience"?
Any good expressions to use in a fit of pique?

Ta.
Am.

[ameerat42]

Thought I'd kick this along. Come on! We don't all use Windows!!

You use Skype on a Mac? Call your mates who use Windows?

What happens when you transfer files?

[MissionMan]

You have a virus called Windows Uninstall Windows and install an anti-virus called OSX.

Just sent a colleague a file from my windows 10 SP3 and he's on Mac. Didn't have any request to log in so it must be unique to one of the machines.

[ameerat42]

I see. Ta MM. Oh, I might add, if he starts up Win 7 on that Mac instead and the Win version of Skype, there's no problem.
(Do you think a Leopard eats the files)

[MissionMan]

I see. Ta MM. Oh, I might add, if he starts up Win 7 on that Mac instead and the Win version of Skype, there's no problem.
(Do you think a Leopard eats the files)

Might be firewall or security settings on Mac.

[ameerat42]

***Woops! Wrong post!***

[ameerat42]

UPDATE on problem.

Here's the go...
If I send a full sized image file from my camera, or one that is nearly full size (bit of editing in Photoshop)
the Mac recipient can get it using normal Skype file transfer.

When I tried with two half-sized files - resampled in Photoshop - that's when he got directed to a Skype website
to download the file. At that website it asks you to enter all your Skype login first, even though you have a Skype session going.

Well, that's it!?<>*&^