The standard settings of Adobe Photoshop prevent that you can undo more than 20 actions. Here comes how you can change this.
Quickest: Go and figure with the screenshot!
Step-by-step: Go to “Edit”->”Preferences”->General… (CTRL+K). There choose “Performance”. Look for the block “History & Cache”. Change the number of “History States”. Photoshop will be able to undo up to 1000 actions.

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