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I've had this issue come up multiple times during my time here: a new user comes in full of enthusiasm and things to contribute but their posts are riddled with grammar/punctuation errors and the format is all over the place. I am comfortable with guiding a user through best practices formatting-wise since there is a bit of an art to doing it effectively on the stack specifically.

However, I have always been hesitant to act to overtly encourage a user to improve their grammar. I know there are many reasons a person might have poor grammar. They could be young and still learning, they could never have learned, or they could even be new to the language entirely (and trust me, I sympathise with anybody trying to learn English as a second language). It is entirely possible that a user might even be unaware that their grammar is poor/hard to understand.

However, often the user's grammar is clearly affecting what may be good content in a way that makes it very hard to tell what they are saying (and acquiring downvotes as a result). When this happens repeatedly, I feel that maybe a nudge to tell them that they should pay closer attention to their grammar to improve their answers, but I'm never sure how or if I should do this.

Correcting the grammar/punctuation is one way of course, but after many answers it gets to be tiring and sometimes it is even unclear what is being said and thus there is no easy way to clean it up.

Should I worry about this? Is this just something that users are expected to "get" just from being around and getting downvotes? Is there an effective way to do this that minimizes the risk of insult? Should I not even try?

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Just edit their answer/question and in the Edit Summary write "Fixed grammar. Improved syntax.".

I'm not a native English speaker and I had noted that in Worldbuilding SE a lot of people edited my questions/answers in order to fix my grammar. I didn't like the fact that I had so many errors and that other people wasted time editing my posts so I tried to improve my grammar.

Now I pay more attention to it and I have found a perfect Chrome extension called Grammarly. The app is "freemium", but the free part is enough to solve the majority of normal mistakes. Even more, you can choose between American, British, Australian or Canadian English (and the premium part can choose between formal/informal/friends/work, and fix "advanced issues").

By the way, Grammarly fixed four errors in this post!

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I like to update the post to my liking and then comment. "I have made some/moderate/major changes to your post. Please look over my changes and confirm that the question still captures your intent and feelings."

This is a stolen methodology, to be sure. I've seen this on dozens of posts, and likely one of my earlier questions as well. I don't find it insulting, while still modeling what is expected.

(and besides, a little silent judging on my side of the monitor never hurt anyone)

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Words are hard, especially when multiple are used in combination. Everyone wants to be understood and everyone's trying their best to express themselves well.

This means they probably don't need reminders or encouragement to try to use good grammar: they're already trying. They're just not as proficient with the language as you are right now. That's OK. They might simply struggle with grammar, or with writing specifically, or they might be ESL, or any number of other things.

To remind them “hey, try to use good grammar” is unnecessary and would probably be condescending. They're already trying. They're doing their best.

Just edit to improve their grammar where you can see how improvements can be made if you feel compelled to do so. Where you are unsure and something is unclear, just ask for clarification or suggest an improvement, e.g. “I'm not sure what you mean in that third sentence, could you rephrase?”. Leave it at that. They'll pick things up and your editing may help them learn writing rules they might have been unclear on beforehand. (I've received comments to that effect before.)

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