Squarespace custom file upload interface broken?

Trying to upload woff and woff2 fonts to Website > Website Tools > Custom CSS custom files section. I've changed my otf files to woff woff2 with transfonter and fontsquirrel. When I go to upload the interface grays out woff/woff2 files but would let me upload otf. Then when I try to drag and drop I get an error (see screenshot) saying woff/woff2 are supported but still can't upload.

Squarespace "support" wasn't helpful, just got links to docs.

Wow, with how documented this issue is it really sucks that their "support" didn't even let me know they knew it was an issue. Thanks @creedon

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Wow, with how documented this issue is it really sucks that their "support" didn't even let me know they knew it was an issue.

It's a bad joke on all of us customers. CSS on SS is a disaster at the moment. Multiple documented issues with CSS and SS is content to let it go on for weeks.

4 minutes ago, creedon said:

It's a bad joke on all of us customers. CSS on SS is a disaster at the moment. Multiple documented issues with CSS and SS is content to let it go on for weeks.

Truly! Especially at a premium price point 😕