Proper Etiquette to Drawing OC's

Glue
Hard Work - Merited Perfect Pony Plot Provider badge with only their own art
Perfect Pony Plot Provider - Uploader of 10+ images with 350 upvotes or more (Questionable/Explicit)
The Power of Love - Given to a publicly verified artist with an image under their artist’s tag that has reached 1000 upvotes
Artist -

I’ve been wondering. Whats the proper way to go about drawing other peoples OC’s. I assume the proper way is you just ask the owner if its alright to draw their character. What if I drew a popular character, and I only drew it in situations similar to other art it is in?
 
Also, what about meme characters? For example, the internet browser ponies. Would I have to hunt down the creator of them for permission? Or could I just draw them as much as I want because they are meme characters?
 
I know its not like I am gonna get sued over it or anything, I just wouldn’t want to come across as rude and upset anyone.
Luna
Luna - For Patreon supporters
Woona - Derpi Supporter
Flower Trio - Helped others get their OC into the 2023 Derpibooru Collab.
Roseluck - Had their OC in the 2023 Derpibooru Collab.
Solar Supporter - Fought against the New Lunar Republic rebellion on the side of the Solar Deity (April Fools 2023).
Lunar Supporter - Helped forge New Lunar Republic's freedom in the face of the Solar Empire's oppressive tyrannical regime (April Fools 2023).
Princess of Love - Extra special version for those who participated in the Canterlot Wedding 10th anniversary event by contributing art.
Tree of Harmony - Drew someone's OC for the 2022 Community Collab
Elements of Harmony - Had an OC in the 2022 Community Collab
Non-Fungible Trixie -

Luna Best Pony~
Generally ask the owner. If you are drawing a gift, and the owner doesn’t specify anywhere on their page that they don’t wish their OC drawn by others, and provided you’re drawing a similar scenario, that is the only case where you may draw without permission.
 
As for the popular OCs (such as Fluffle Puff, Blackjack, etc), you generally can draw them, unless again their creator explicitly forbids you from drawing them.
 
In the end of the day, the booru has no real takedown rules for OC owners, so draw what you wish, but beware that the art may still be taken down if it’s in violation of Rule #0.
Interested in advertising on Derpibooru? Click here for information!
Ministry of Image - Fanfiction Printing

Help fund the $15 daily operational cost of Derpibooru - support us financially!

Syntax quick reference: **bold** *italic* ||hide text|| `code` __underline__ ~~strike~~ ^sup^ %sub%

Detailed syntax guide