"Taking this down is sexist. I have every right to show I have a better body than Putin," the 39-year-old actress and talk show host said on her Twitter feed after the spat erupted Thursday night.
The picture showed Handler on a horse, next to one of a similar pose to Putin in 2009, which provoked much amused debate at the time over his attempts to present him as an all-action leader.
But it was taken down three times in succession by the image-sharing service, which blocked it with a message saying "@chelseahandler, We removed your post because it doesn't follow our Community Guidelines."
Those guidelines ban "nudity and mature content."
Handler countered: "If a man posts a photo of his nipples, it's ok, but not a woman? Are we in 1825?" adding: "If instagram takes this down again, you're saying Vladimir Putin Has more 1st amendment rights than me.
"Talk to your bosses," she told them.
She subsequently reposted the picture to Twitter, where it remained viewable Friday, albeit behind a warning which said "The following media may contain sensitive material."
"You can now find my dogs and my breasts on Twitter only where my followers have the right to choose what they say. Bye bye instablock," she wrote.For the latest tech news and reviews, follow Gadgets 360 on X, Facebook, WhatsApp, Threads and Google News. For the latest videos on gadgets and tech, subscribe to our YouTube channel. If you want to know everything about top influencers, follow our in-house Who'sThat360 on Instagram and YouTube.