As we all know, the best laid plans etc and that is even more so for chastity plans. No matter how well you plan, something can always go wrong.
That you know and accept this is a huge step in being happy in your chastity. It is perfectly normal at the beginning of a chastity journey for things to put a spanner in the works. Whether it is an ill fitting device, skin irritation or just real life conspires to make it impossible to lock at that time.
This is perfectly normal and acceptable to a Keyholder. Safety is of the utmost importance to everyone in this lifestyle. No one wants the chaste male to be ill or to cause him any more discomfort than is provided by the wearing of a device. So if your device is causing problems for whatever reason then they need to be addressed before continuing and possibly causing some real damage.
When making chastity plans, it is probably a good idea to think of it in different stages. When first wearing a device, you should have the key readily available in case of skin reactions, bad fitting etc. Even if you switch to a lock with someone else holding the key, having the ability to cut off the lock in case of emergencies is a sensible precaution.
If using a combination box, it is always wise that you are able to contact the person with the combination quite quickly. I get emails on my phone so normally the longest it will be until I know the combination is needed is probably an hour. If I am out and about for some reason and there may be a possiblity of it being longer then I am happy to give my number so I may get a text in case of emergency.
Chastity Plans like any other plans can go awry. It is how chastity works and it makes for an interesting and varied experience.