There's only one safe assumption.
The question is a little vague, so I'm going to make some assumptions:
- You both attend the same school.
- Your "personal account" is an account elsewhere -- like GMail, Outlook.com, or some other non-school-related account.
- You're not using the school equipment or network to send your message; perhaps you're doing it from home.
Yes. You can only assume that -- unless you've taken specific precautions -- absolutely the school will be able to see all the email that comes and goes on its systems.
Whether they actually look at it or not is another question.
Let's examine that and consider what those "specific precautions" I mentioned might be.
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Can your school see email?
Unless you encrypt your email or otherwise avoid your school's email and internet infrastructure completely, it's quite easy for them to examine the content of messages traveling across their systems. While it's likely rare that they do look, or care, there's no way to know for certain. If there's any concern at all, the only safe approach is to assume that they do.
School as your ISP
I've written elsewhere that your ISP can see everything you do.
Your school is no different. They are providing your internet connectivity through their equipment, and as a result, they can monitor everything that travels across it.
That's doubly true if they're providing not just your internet connectivity, but your email accounts as well. By providing your email service, they have even more ways to examine the contents of what you send and receive.
Technically, it's a very simple thing for your school to see email you send and receive.
Outside email to your school
Like I mentioned earlier, I'm assuming your question is about sending email from a non-school account outside your school's system -- perhaps you have a private account somewhere else -- using an internet connection and equipment that is also not related to your school -- to someone who's at your school.
Yes, your school can see email you send to someone who's there. All it takes is one end of the conversation to travel across school equipment or services (like email), for them to be able to monitor the conversation should they want to.
Do they want to?
Does your school see email?
Just because they can see your email doesn't mean that they do see your email.
As I said, it's a relatively simple thing for an email provider to examine the contents of email being sent and received. But just because it's simple doesn't mean someone is actually doing it.
Unfortunately, there's no way to tell.
There need not be any outward sign to you or any recipient at your school that email has been read by someone else.
They could be monitoring it all, and you'd never know.
The only safe assumption
Because they can, the only safe assumption you can make is that they are, and act accordingly.
It may not matter to you. Honestly, it probably shouldn't. I'm sure the intent is that this type of monitoring would be used only for inappropriate activities or issues that "break the rules," so to speak. Don't break the rules and you'll be fine, monitored or not.
But power can also be abused.
While it's unlikely anyone is taking the time, paying someone else to take the time, or has an interest in what you're writing in email, there's no way to know whether they are or not.
Two specific precautions
There are two approaches to avoid the issue, only one of which really solves the problem.
You and your recipient could use encrypted email so that only you and your recipient can see the contents. There are two downsides:
- Your school can still see the email addresses involved.
- Your school can see that you're encrypting the contents.
They may assume -- perhaps rightfully so -- that you have something to hide. Or they might not notice. There's no way to know.
The safer approach is to avoid the school's systems entirely. You and your recipient could use email accounts not associated with the school at all. You'd also need to avoid using school equipment, which could still be monitored, to send and receive email.
If your school never handles it, they can't see it.
It's about more than email
Everything I've said above is equally true for most instant messaging, social media, and chat services. Using school equipment opens up the possibility that they could monitor your conversations. Even "https" conversations.
Once again, there are two precautions, one better than the other.
Use an end-to-end encrypted messaging app like Signal or Telegram.1 If you're using your school's internet connection, they'll be able to see that you're using these tools, but will not be able to see what you're saying.
The better solution is as before: don't use your school's internet connection. They can't see what's not on their systems.
It's about more than school
While I've answered this question pertaining specifically to school, the answer is exactly the same for the workplace: your company can see everything you do. It's not even illegal.2
So when using company equipment and/or company services, keep in mind that whatever you're doing may be subject to scrutiny by the boss.
Or not. The same problem still applies: there's no way to know.
You can only assume, and the safest assumption is that you can be and are being monitored.
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Footnotes & References
1: Yes, WhatsApp, and even Facebook Messenger, claim end-to-end encryption. There's enough distrust of Facebook, which owns them both, to cast doubt on the absolute truth of that claim in all cases.
2: I'm no lawyer, but I understand this to be the case in most jurisdictions.
One additional possibility which some schools have in place. They may have software which monitors communications for certain keywords pertaining to drugs, violence, bullying or harassment etc.
This subject about who can see. If your are on your work computer or logged in via your home computer. THEY CAN SEE IT. School and College also. They tell you they can and they may check from time to time. Every key stroke is logged and saved somewhere. They have programs that look for certain things which might cause a closer review. But unless there is a problem they don’t look. Too many key strokes. Thank goodness. Stay out of trouble and use your phone instead.
How far back can a school access emails? If I deleted an email can they see my deleted stuff? If it is permanently deleted can they see it? Once I leave how far back can they access my emails?
There is no specific amount of time the school holds your emails. It’s at the discretion of the school, and yes, the can see your deleted emails.
There’s simply no way to know. It could be days, it could be decades.