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I'm sorry that you are having trouble syncing fonts from Typekit!
> Then I have to open the CC App, which always needs to do a half hour update it seems.
The Creative Cloud desktop application does need to be running on your computer in order for the fonts to sync. If you use font sync regularly, try adding the Creative Cloud desktop application to the startup options on your computer, so that it will run automatically whenever you restart or after shutting down the computer for the night.
Once the Creative Cloud desktop application is running, all the fonts you have synced from Typekit should be listed in the Assets > Fonts tab (screenshot below) within a minute or two.
If you find that it's taking longer than that for the fonts to sync, or they still aren't available to InDesign once they show up in the Fonts tab, please make a note of time by the computer clock the next time this happens, i.e. you open the Creative Cloud desktop application at [time] and the fonts don't sync until [time].
Then send the sync log file from your computer with those two times to email@example.com, and our team can check for any issues that are slowing down your font sync. Here are instructions on where to find the logs on OS X and Windows:
> And also, why if I have synced the font on both of my computers does it keep unsycing?
This sounds related to not having the Creative Cloud desktop application running on the computer(s). If the problem persists with the Creative Cloud desktop application always running, please send some more details on what you see happening. The CC app is open, but the fonts disappear at random, for example, or something else?
Please feel free to email us (or post here) any screenshots to help explain the issue! Here are instructions on how to take a screenshot, in case you need them: http://www.take-a-screenshot.org/
I agree with the "nightmare" part. I'm only working on my files using InDesign on one machine, and yet, because I have used TypeKit fonts in those files, I'm constantly prompted with 'missing font' messages upon opening said files. Sometimes syncing the fonts works, but more often than not it doesn't. And, often, even when syncing the fonts works on opening a file, I'll still receive a 'fonts missing' error upon attempting to export the file to PDF and, here again, sometimes it works and other times it doesn't. The error messages aren't helpful, either, as they direct you to the Adobe Creative Cloud desktop app for "more information"—but there isn't any.
I've gotta say, Adobe are pretty fortunate that InDesign has no real competitors. If it did, very few people would put up with the poorly-implemented, inconvenient, bug-ridden mess that is TypeKit.
Ben from Typekit here. We're currently looking into this very issue. If you would like to help, you can reach out to us at: firstname.lastname@example.org and we'll ask for some diagnostic details.
We really don't like when this happens but need to gather more information to determine when/why it's happening. Feel free to reach out to our support anytime. We appreciate the feedback and help.