Make sure you're logged in with the same CC account on both your Mac and on your iPad?
I do have the same CC account on both. I checked just in case, but it also makes sense since the option "Save PSD to Creative Cloud" does work from my iPad and I can access those files on my synced folder on my Mac. Also, with the "Send to..." options the computer seems to receive the message that "something" was sent from the iPad (which I assume is the result of a dialog between my iPad and CC) but somehow it doesn't go through with it and gives the error message.
I am sending to both Mac and Win successfully. I don't have any permissions set to anything but default.
Even my Sync Settings in Ai are set to "None"
You may want to just double check your Ai preferences to ensure that it does see your correct CC account.
If you could post your iOS and OS versions that would help too.
I suspect that there may be something in the new desktop OS that is blocking you from pushing a file that is automatically opened.
**Possible connection fix: LOG OUT / LOG BACK IN to your iPad app / CreativeCloud app. It's possible that the connection needs a refresh.
I have an updated version of Creative Cloud - Illustrator CC (Win 7). Sketch 2.2 on my updated iPad (iOS 8.3).
When trying to a simple one layer Sketch image with "Send to Illustrator", the following error message appears in Illustrator CC:
"Version 2 of the Adobe Photoshop Sketch file format is not supported in the version of Adobe Illustrator."
What to do?
I get the same error warning on Illustrator CC 2014 (Win7) on updated iPad (iOS 8.3),
BUT, I'm not sure what it's balking about.
1) Click OK
2) Select the image
3) In the OBJECT menu pulldown, select "Sketch & Line Art" and then EXPAND TO PATHS
The vector information from Photoshop Sketch is restored.
Is your desktop machine where you are running Photoshop and Illustrator in a corporate network within a firewall ? If that is the case, it could be possible that some data sent to the desktop apps have been blocked and the "Send to Photoshop/Illustrator" functionality can not be completed. If this is your case, can you try the "Send to Photoshop/Illustrator" outside of the corporate network? The "Save PSD to Creative Cloud" is a different workflow as the files are stored in the cloud.
Hope this helps,
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The warning message you are seeing ""Version 2 of the Adobe Photoshop Sketch file format is not supported in the version of Adobe Illustrator." will be addressed in the next release of Adobe Illustrator. You can dismiss this warning message and still continue your work, including "Expand to Paths"
Hope this helps,