@david@collantes.us While you’re typing? I guess this could be used as a starting point (doesn’t work on the very first line):

inoremap <CR> <Esc>:r!date +"\%F \%T"<CR>A 

What’s the end goal here? 😅

@movq@www.uninformativ.de wow, that almost works as I want it! Only think missing is the first time stamp, on opening. Hmm…

This works! Any way to streamline it further?

autocmd BufNewFile * call s:InsertTimestamp()
inoremap <CR> <Esc>:r!date +"\%F \%T"<CR>A 
function! s:InsertTimestamp()
  call setline(1, strftime('%Y-%m-%d %H:%M:%S '))
  normal! G$
endfunction

@david@collantes.us Ah, I just went to bed, great to see you figured it out. 😅 I probably would have ended up with something similar (but I’m not a Vimscript guru). 🤔