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Is there a way to automatically change the TODO keyword into PROGRESS when I clock in to an agenta item/task? If so, how? (OK, this isn't a big deal, I currently press I t p to achieve this, but it would be nice to have (and save 50% on keystrokes when including the Shift for I).)

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You should set org-clock-in-switch-to-state to the intended state:

(setq org-clock-in-switch-to-state "PROGRESS")

Documentation: Set task to a special todo state while clocking it. The value should be the state to which the entry should be switched.

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    Very nice! This also alludes to how to set the todo state to WAITING when clocking out... :-) – AstroFloyd Apr 18 at 8:42
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Sacha Chua achieves this by doing the reverse, clocking-in when the state is changed to 'progress' (instead of changing state when clocking-in): https://sachachua.com/blog/2007/12/clocking-time-with-emacs-org/

Hopefully that helps!

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