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I finally told me parents after 3 years, 3 iuis and 3 fresh ivf cycles. I was flying out to CCRM, and they dog sit for us, but it was still hard. At first i called and told her we were going to CO and she asked why, and i said just because. I called back hours later and said i was going to see a doctor about having a baby. It was HARD to get the words out.
At first i was really upset i said anything. The first thing she said was "that's it? There's nothing else wrong, right? " (there's a lot lost in translation, English is not her first language and i was sure how to explain it in her native tongue which didn't help). Her reaction of That's it was tied to her immediate thought on my health, i wasn't dying which would be her first concern as a mother. She didn't understand the situation at first i think, asking (in my mind) stupidly simple ttc questions. And I was just getting mad taking about it. Of course after i calmed down i understood this was new to her and she just asking about what little she knew of ttc. (4 kids 2 yrs apart, no really trying for her I'm guessing)
Weeks later i guess she'd done since research and talking to people and got a better understanding. She asked me some follow up questions, told me what she'd learned and then said she would stop asking cause she didn't want to pester us, and for me to let her know updates when it happens.

So i guess from my story, Id say try to work it into a conversation. Maybe warn them you have something neither good nor life threatening to tell them. Be prepared for them not to know at all how to react or what to say. Maybe tell them how you need them to be supportive, what not to do especially if there are things you know you don't want to deal with. Tell them what you want them to know, and ask them not to pry if you don't want to share any more. If they start offering advice you don't want, just tell them what you think. .. yes, i know, no that won't work, I'll be discussing with my doctor, thanks but I'm all set, i don't want to discuss this right now, please don't bring this up unless i do first....
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Good luck. I definitely feel better that they know now and I'm not hiding this huge secret and part of my life anymore.

I am not close to my inlaws and was nervous to tell them because they are very religious. However, they were very supportive and good about not asking a lot of questions. My only complaint would be that they did not understand the "secret" part of it and I know it was told to other family members when I did my Ivf as well as my mil prayer chain and patients!

Could you enlist someone, like a sister or SIL to bring up when you guys are planning to start a family, as a way to bring it up?

I still haven't told my ILs - my DH doesn't think we need to, but I do want to.

My parents have been in the loop pretty early on. After about 3 months of trying my mom was getting antsy and I told it her wasn't "that easy" for everyone. Around 9 months or so she asked if we "knew how to do it right" and that was like OMG!!!!

My mom was was supportive the whole way through when I started seeing a RE. I just had to moderate what I told her, like she would ask when my DH was going for a SA and I told her she didn't need to know the date My dad gave himself injections when I was a kid for a couple years so I asked him for advice on giving stomach injections before I did my first IUI and he was also supportive but never asked me any questions.

I hope things went well for you and your discussions with your family. It is really nice to have someone other than DH who is family to talk to sometimes. And it definitely curbed the amount of times my family was asking if I was pregnant yet.

DH talks to him mom every day so she was aware as soon as we made the appt's. I am more private and don't talk to my mom daily. I finally sent her a message about it recently b/c she had made a few comments like "I'm ready for another grand baby".. I wanted to say so are we!!!!!!!!!!!!!!!!!!