Right, but what you probably aren't understanding is how sneak works.
If you use the "sneak" command, you get the "you attempt to move silently message." You do not, however, get to see for certain whether or not you are sneaking. The only way to tell if you don't have other PCs to tell you is if you can also hide as talked of above.
If you have snuck successfully, then you are given the "sneaking" status, which is a status effect that does not appear on the affects list. Sneak wears off either A) after a certain period of time, B) if you flee, or C) if you try to sneak again.
The first example you have there is you trying to sneak while already sneaking, and as a result you are actually -losing- your sneak that you had beforehand, it's just that the messages are inverted. In other words, it should logically read in this order:
>sneak You no longer feel stealthy. (You were sneaking before you tried to sneak just now, and lost it as a result of trying to sneak again) You attempt to move silently. (You have now attempted to sneak again, and you do not know whether or not you succeeded).
Sneaking is determined by your mastery of sneak, the number of humming items that you are wearing, and maybe whether or not you are over half carrying capacity. In my experience if you have sneak mastered and aren't wearing any humming items, you can rest in the knowledge that you will sneak every time you use the command. In fact, if you have sneak mastered it isn't a bad idea just to sneak every five minutes or so to reapply it so it doesn't wear off without you noticing.
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