Hi Kevin,
Nice to hear from a fellow T1D! I’m guessing you won’t have enough time and also want to avoid the expense of getting a doctor’s letter to accompany your medication?
In the UK we’re always advised to carry a letter for when we pass through security but not once have they looked at it. I place any liquids into a clear plastic bag but my box of literally 100 needles, lancets, testing strips, and glucose monitor go through in my bag without any hassle. The only time I’ve had an issue is when they wanted to check my glucotabs because they’re a food item.
Obviously there’s no guarantee and each airport will have different rules, so I’d consider trying to phone the airports you’ll be travelling through directly and see if you can get a clear answer that way. Otherwise, just take all your bits of kit out and leave it on display in the tray, chances are they’ll have seen it hundreds of times and it’ll fly through. If you have something like a repeat prescription though or labels on anything proving it’s yours, that could be a handy back up.
Hope this helps reassure you slightly even if it isn’t a definitive answer. Good luck and safe trip!