@Ginsly,
I have used these connectors perhaps 8-10 times in various projects over the past 2-3 years - so I'm definitely not an expert on them. Hopefully others with more experience will also chime in.
Anyway, I first tried crimping without a tool, and it was a total disaster - it's a tight fit getting the crimped piece into the plastic surround, so if you generate a distorted shape then it just won't go. Basically, I just repeatedly screwed up.
So I bought this fairly inexpensive crimping tool from Amazon, and things went much better. (My occasional use did not warrant a better quality and more expensive tool):
There are several such tools that look the same as this, so there may be other vendors/places to get it for less. This one seems reasonably sturdy, as you don't need to squeeze the crimper especially hard for it to do its job. It also helped me to look at all the photos on the Amazon webpage - with a little trial and error, they helped explain it's use, including the hard-to-see release trigger. My recollection is that the manual was pretty minimal.
Good luck to you, I hope this helps!
Note added later:
For all I know, it may also be possible to buy pre-wired jumper cables of the right length for these JST-XH connectors, if so then you might not need a crimper after all. I didn't explore that as I have always required custom lengths to fit my specific needs. Anyway, just a thought...