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Baskerville supports ligatures, as you can see in this screenshot from Word:

Word screenshot

However, in Photoshop, the ligature options are greyed out when using Baskerville:

Photoshop screenshot

I can get the ligature to display by manually inserting U+FB01 , but that's not ideal. Is it possible to enable automatic Baskerville ligatures in Photoshop?

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Unfortunately, Photoshop doesn't recognize the ligature table in your version of Baskerville. I get the same result with my TrueType version from Monotype. I have tested Adobe's ITC New Baskerville Std (opentype) and it does work. It looks extremely close to the Monotype version I have, so that's a good way to go if you have it, or can buy it. Aside from that, your method of manually inserting the glyph using the ascii code is the next best solution.

enter image description here

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Baskerville doesn't allow me either to toggle ligatures on or off. It works with other fonts like Myriad Pro Regular for example, the fi ligature in not grayed out in the character's menu.

I see 2 options:

1- Change the font

or

2- If you really want to keep this font, create your text with the ligature in a word document then save it in PDF with a font size big enough, then open it in photoshop and take it from there.

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