Is this normal?

As you say, he's fine leaving others, so he clearly understands the concept of separation, but maybe you're right and he is just sensitive.

If he isn't incredibly distressed, could you have a wee routine? Maybe (and this is just a silly suggestion) matching wristbands that you press together when you're leaving and say 'see you soon!' or something similar?

I don't have kids myself but I was a wee bit like your son at a similar age, especially with regard to my older sister. She came up with the system I've described above and it worked for us.

OP didn't say that it impedes his independence, though. Just that he sheds a little tear - which I'm sure he could work out how to disguise/hide if it bothers him other people seeing it.

TBH I think I was probably about this sensitive at 10 I didn't cry on school mornings, but I remember really struggling one performance that my mum wasn't able to make it to and I didn't like it if she came to school for some reason and had to go away again. I also didn't cope very well with overnight visits - sleepovers I had to be picked up from and then only got into them later in my teens, with friends I was extremely comfortable with.

I went on the French Exchange in Y10 and was an emotional mess the entire time D: even going away with college aged 16 I was upset and homesick on the first night - then the second night I discovered alcohol and this cured everything NOT that I would suggest that as a strategy!

Anyway, I have gone on to do lots of independent things like moved out of home aged 18, applied for various things and done various things I didn't feel confident about, left an unhealthy relationship of my own accord, and moved abroad when I was 25. So I reckon he will grow out of it and you don't need to push him into that, he will do it when he is ready.

If there are no additional needs or anxiety, I'd be inclined to think you need to encourage him to have a bit more independence from you. It's lovely that you're so close and he clearly loves you very much, and there's nothing wrong with being sensitive, but to cry every time you drop him off is a bit much. I'd be concerned that he might start to get bullied about it if it carries on when he's older. Have you asked him why he gets so upset at the separation? Is he worried about something happening to you?

My 10yo is the same but is diagnosed with ASD and ADHD. But doesn't do a little cry, it's more of a massive meltdown.... so I've lost touch with what is meant to be normal and what isn't, but if it's any comfort (probably not) I'd see a little cry as a win!

I was like this why I was eleven and had just started secondary. Used to worry something might happen to Mum and I'd never see her again. Completely unfounded worries.
She just supported me with lots of love until it passed. It didn't help that we were reading a sad animal story in class and I used to cry about that.
Just wanted my Mum.
It will pass OP. And Mym lived until her late 80s xx

My DD was.

She's autistic, very very subtle presentation ('sensitive' and anxious). Also experiences big separation anxiety from me now at age 13

I think this is normal. My child has gone through similar, a bit teary when I dropped them off but not with Dad. It was a phase for a month or so. Teacher came to ask me if anything was going on at home etc as child settled after about 10 mins and was fine in school. Have you spoken to school about it? Only thing we could think of was child was getting tired and knew they’d get more sympathy and hugs with me if they got a bit clingy at drop off.
Speak to school and if all okay hopefully just a phase and you can work on positive chat before drop off

Bless him I am sure there isn't anything wrong. He does sound sensitive, a deep feeler. Perhaps he'll be an artist or musician?

Have you read The Highly Sensitive person? Might be something that resonates and is helpful.

Aw he sounds a lovely boy x

Are you away a lot?

Just trying to think why he might be so upset?

Is it that you are away a lot, and therefore he genuinely does miss you

My now 11yo was a bit like this at age 8. Now he is at secondary we have had to work really hard to get him confidence enough to walk home. We suspect my son has ASD and I know that can impact how some children find transitions. Otherwise, I think some children are just sensitive, gentler souls. He won't be like it forever, I would just give him the support he needs until he grows out of it,

There's something going on at school. DS started getting upset about going to school at the same age. It was bullying by the Y4 teacher. She had a track record. It all came out. After a meeting with the Head it never happened again. He left at the end of Y4. She left two years later. Nobody had dared complain about her before. We could because we had choices.

What about when he leaves you to go to other places with other people? Or is it just leaving you at school drop off?

Obviously isn't not normal for a child of that age to cry when they go to school, or even when they leave their mother.

You need to discuss with him how to handle this situation. Maybe don't do drop offs for a while, so he breaks the habit.

Well, ask him if there’s anything you can both do to help when you’re dropping him. Some form of words, note in lunchbox, a reminder you’ll see him in exactly x hours? Something he can suggest?