Fonts showing as .exec files

In Ventura, old legacy OS 9 style TrueType fonts, and the outline portion of Type 1 PostScript fonts display with an EXEC icon. Actually, it's been like that since at least Monterey.

There's technically nothing wrong. It's an indication these fonts are on their way out. I wouldn't be surprised if either is allowed to be used with the next major release of macOS.

For old TrueType fonts, you can still activate those with Font Book, or any other font manager. For Type 1 PostScript, Font Book ignores this font type. But you can still use them by either activating those fonts with a different font manager, or manually placing them in the Fonts folder of your user account.

Be aware all recent versions of Adobe's software will not load T1 PS fonts. They have been sent to the dustbin of history.

The Unix EXEC icons won't change no matter what you do. But that's irrelevant. The OS just no longer assigns that font type the icon it used to use.

That message is now normal for Font Book in Ventura. It will not activate Type 1 PostScript fonts, even if everything you have for a set is correct.

You show eight outline printer fonts and what should be the suitcase of screen fonts for the set (HTF Gotham TM). If you place those in the Fonts folder of your user account, you should then see those eight fonts in any app that recognizes T1 PS fonts.

That is by far the best choice. Type 1 PostScript is just short of dead. I think within two years - tops - no modern OS or app will let you use them.

Watch this great seminar by Thomas Phinney on why T1 PS fonts need to go away. He's been involved with fonts practically since the beginning of computers. Originally with Adobe for many years, and currently at the head of FontLab.