"Show transform controls" missing from my toolbar

The easiest workaround would be create two tool presets, one with and one without the checkbox enabled. You can record those into an action and assign a keyboard shortcut. You can also copy as Javascript and use Batchplay/UXP scripting for more control.

async function transformControls() {
    let result;
    let psAction = require("photoshop").action;

    let command = [
        // Select tool preset “Move Tool 2”
        {"_obj":"select","_target":[{"_name":"Move Tool 2","_ref":"toolPreset"}]},
        // Select tool preset “Move Tool 1”
        {"_obj":"select","_target":[{"_name":"Move Tool 1","_ref":"toolPreset"}]}
    ];
    result = await psAction.batchPlay(command, {});
}

async function runModalFunction() {
    await require("photoshop").core.executeAsModal(transformControls, {"commandName": "Action Commands"});
}

await runModalFunction();

I'm having the same issue and use it all the time too. I don't understand why they would remove this in their "update". It's not very convienient having to select/unselect in the settings (gear icon).

For some reason, my "show transform controls" checkbox is now hidden behind a gear icon on my toolbar. 

 

By @PonytailsDesigns

I think the reason is that your software was updated to the latest version.

I'm not a fan of this change either.

EDIT: Adobe listened to user feedback and moved this back in a later update!