The FIRST thing we do is check (and double check) the drug laws/regs of the country(ies) we are traveling to.

Sometimes meds that seem innocuous "here" could lead to nasty consequences "there".

Even traveling within the USA (where we are citizens), we still keep physician letters for any type of medication/devices "of potential interest".
We also keep the meds in properly labelled containers, together in a little zipped bag kept in a carry on bag. (We've asked the local pharmacist for a properly labeled, smallest size container for "x cays supply" of each med, where "x" = expected trip length plus extra in case of delay.)
We just keep that ready to go, for any trips.

And NEVER let that bag out of your sight unless the meds are locked up, if those meds are truly critical!
Sometimes I think the bellboys/etc., must think we are acting like we are carrying the crown jewels. But if a few key meds were "gone", we might be heading home, and fast.

In some cases, we've emailed the appropriate "department" in another country, listing the meds we take, well in advance, asking if there are any special permissions or limits on the list. Sometimes it was a surprise, something we thought would be "no problem" did have a restriction... or was totally prohibited, or needed another level of permission. All it required was a letter from an M.D., and a copy of the original Rx.

It's so much easier to "be prepared", as the old Scouting motto goes...

In Japan, we had to show one document upon arrival, with the quantity being brought "in" listed.
And then, to get the permission, we had to state the quantity being "taken back out". Well... it's not always exactly "x" per day.
So that's what I wrote, and for the quantity, wrote something like "less than <quan brought in>" and that passed muster.
If we had needed to bring more than than the amount ordinarily allowed, then we'd just have needed to request permission.
And when departing, we just needed to show the "departure" form. (Both arrival and departure forms had special stamps/signatures.)

NOTE: A British woman was just sentenced to 3 years in an Egyptian prison for bringing "pain meds" to her Egyptian husband.
I'm sure there's more to the story than written in the popular press blurb, but... it made us really happy that we've always bothered to take all of the proper precautions, per the host country.

British tourist gets three years in Egypt on drug smuggling charge - CNN

It seems obvious that at a minimum, she wasn't thinking it through.
However, note that the British listing of "travel substances" added that particular med a month *after* her arrest.

For us, why risk anything, and why worry?
We just follow the rules. Thus far, we haven't encountered any jurisdictions where we absolutely could not bring in a med that we truly *needed*, but that could happen.
If so, we should know in advance, and adjust our travel plans accordingly, but we sure hope that won't happen.

GC