Select the object then in the appearance panel use the fly out menu to Clear Appearance, now try the grad tool. An easy way to set the object to a simple grad would be to select the object and tap the decimal point key in the lower right of the ten key numerical key pad. Answer from PrepressPro1 on community.adobe.com
Discussions

freeform gradient tool is grayed out and not working. – Adobe Illustrator
I have updated Illustrator and the new freeform gradient tool is grayed out in the gradient panel. It is not usable. More on illustrator.uservoice.com
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October 21, 2018
Gradient tool issues - Adobe Illustrator - Uservoice
I just upgraded to Illustrator 23.0.4. The gradient slider does not show when creating an angle or adjusting. there is actually total malfunction of the tool itself. At this point I don't have use of the gradient and I'm in the middle of a job for a client. who is going to pay me for my time while I'm trying to work... More on illustrator.uservoice.com
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Why doesn't the gradient tool appear over the object I've applied it to in Illustrator CS6? - Graphic Design Stack Exchange
Why doesn't the gradient tool appear over the object I've applied it to in Illustrator CS6? I have to click and hold down to adjust the size of the gradient on an object or just use the gradient wi... More on graphicdesign.stackexchange.com
🌐 graphicdesign.stackexchange.com
July 26, 2013
Updated to CC 2020, and the Gradient tool is not working correctly?

Sounds like an accidental reversion on Adobe's part. It's doing that in 2020 for me as well.

The live gradient update was only just added in 2019 in the first place; did you just start using AI this year?

Personally I prefer the old way, things start getting really slow when I try to adjust a gradient that's one fill/stroke in a complicated appearance stack.

Anyway. Go to the uservoice site and file a new bug, maybe it'll get fixed, maybe not.

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November 6, 2019
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Adobe Illustrator
illustrator.uservoice.com › forums › 601447-illustrator-desktop-bugs › suggestions › 35782336-freeform-gradient-tool-is-grayed-out-and-not-worki
freeform gradient tool is grayed out and not working. – Adobe Illustrator
October 21, 2018 - I have an object selected, I then go to 'Window>Gradient' and on the 'Gradient' tool panel I can see the three 'type' icons for 'linear,' 'radial,' and then 'freeform.' But the 'freeform' one is completely greyed out and I cannot click on it.
Find elsewhere
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Adobe Illustrator
illustrator.uservoice.com › forums › 601447-illustrator-desktop-bugs › suggestions › 36623800-gradient-tool-issues
Gradient tool issues - Adobe Illustrator - Uservoice
1. Handles on on object's Gradient Annotator are difficult to adjust once a gradient has been dropped. Usually, handles simply don't respond. User needs to start from scratch and create a brand new gradient rather than make small adjustments ...
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Wyzant
wyzant.com › resources › ask an expert
Gradient Tool is blocked on Illustrator cs6? | Wyzant Ask An Expert
April 20, 2019 - Easy one—the Gradient Tool isn’t yet compatible with STROKE gradients. Click on the FILL icon and you’ll be back in business. It only took them about 25 years to figure out stroke gradients at all!
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LinkedIn
linkedin.com › all › digital illustration
Troubleshooting Gradient Mesh Issues in AI
March 21, 2023 - ... Another way to troubleshoot gradient mesh issues is to apply the mesh envelope to your object. The mesh envelope is a feature that allows you to warp and transform your object using a mesh grid, without affecting the original gradient mesh.
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Creative COW
creativecow.net › forums › adobe illustrator › illustrator – gradient angle not working
Illustrator – Gradient Angle not working - Adobe Illustrator - Creative COW
Click one of the markers left or right and choose your colour. To create new ones just click below the gradient-line. In the Toolbar activate the Gradient-Tool (G) and draw any line in your shape to change the gradient position or put the number into the Angle-window and hit return.
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Vectips
vectips.com › tips-and-tricks › where-is-my-gradient-annotator
Where is My Gradient Annotator? - Vectips
March 1, 2012 - This was the first I even heard of this tool but after a bit of playing it disappeared on me. The key for me is line 4 of the original Tips and Tricks. You need to have the gradient tool active…I am such an idiot.
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Adobe Illustrator
illustrator.uservoice.com › forums › 601447-illustrator-desktop-bugs › suggestions › 38964745-cc-2020-gradient-tool-not-updating-result-live-on
CC 2020 gradient tool not updating result live, only when releasing the mouse button (like in CC 2018) – Adobe Illustrator
November 6, 2019 - In CC 2019, when using the gradient ... applied/moved it. Now in CC 2020, the tool has reverted back to how it was in CC 2018, meaning you have to let go of the mouse button to see the result....
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Adobe Illustrator
illustrator.uservoice.com › forums › 601447-illustrator-desktop-bugs › suggestions › 39687628-freeform-gradient-fails-at-transformation
Freeform Gradient fails at transformation. – Adobe Illustrator
February 12, 2020 - But it allows it if it is in some kind of object transformation. If this happens, the only work around I've found is to set the object to a non-freeform gradient, and then switch back to freeform and re-lay out the whole thing.