I FOUND IT! I FOUND THE ANSWER!
Okay, maybe not the final answer, but part of the problem! Asks keep getting eaten. Which is a big problem when you’re doing something anon and don’t want to ask the person “did you get it”?
If the ask contains an ellipsis without a trailing space, it gets eaten. It says delivered, but it goes nowhere.
So “Well… then” will get delivered but “Well…then” won’t!
Hopefully this helps in getting your asks actually delivered.
Post I made for my RP account, but very relevant elsewhere.
After discovering this, I tested it. Five different accounts between two people, anon vs not. No matter what, without fail, if the trailing space was missing, the message was not delivered.
I contacted Tumblr staff. They were already fully aware this was happening, but it is not documented anywhere. Nor do they seem keen on giving their users a warning about it in any fashion.
Help me spread the word because the staff won’t!
The reason this happens is the same as the reason they won’t fix it: this is how they prevent people from sending links in asks. Instead of using any of a number of easily implemented regular expressions for parsing/recognizing URLs, they just declare that any time there are words on either side of any number of dots with no space, that’s a link. So if you forget to space between sentences or you wind up one character short and decide to trim some spaces, you can also fall afoul of the filter.
It’s a very lazy, slapdash solution and the fact that they choose to make the asks silently fail to deliver instead of telling you a link was detected or whatever makes it even worse.