how do you know when a condom is just too small?

Question

who knows

Answer

It’s very unlikely you can literally put one of your limbs in a condom. They fit over your head.

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Most condoms are made to fit a variety of penis sizes and so u don't have to worry much. However, men who are on the larger end of the wand would need bigger sizes cuz the condom would just feel too tight and uncomfortable for them.

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when it cuts off his circulation and they keep breaking.  These girls always say "they can stretch blahblahblah", condoms are not a one size fits all.

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for us we determined it was a tad too small whenever we couldn’t roll it down his penis easily, as in we would roll it all the way down his shaft but it would want to roll back up at the base. it also didn’t go as far down his shaft as we would like. 
we went one size up and the extra millimeters made a difference. it’s still tight enough but we don’t have to fight as much to get it on. 
he can still fit into normal size if we have to though. condoms are pretty accommodating

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when it’s too tight. yes condoms CAN be too small also! just because you can stretch it around your entire head doesn’t mean it’s not uncomfortable

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If the condom is too tight or if it doesn't fit all the way down his shaft properly.

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female or Male condom? I have no experience with females, but normally guys will complain it being to tight, or to short.