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A few weeks ago I tried to take my Trek road bike for my first ride since last fall. It has been sitting in my (uninsulated) garage over throughout the winter and when I tried to inflate my tires the pressure gauge on my pump showed that they wouldn't inflate. Does this sound like a problem with the pump or the innertube?

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That's a design feature of the bike, they do that to encourage you to ride all year round. Seriously, you say tires - plural. If the problem is affecting both tyres then look at the pump first. I say this just because its unlikely that two independent tyres would suffer the same problem. –  PeteH Apr 24 at 17:01
    
Presta or Schrader btw? (if unsure see here.) Probably won't make a difference but you never know. –  PeteH Apr 24 at 21:47
    
@PeteH they are presta valves –  indieDev May 13 at 1:40

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Does air leak out when you depress the valve? If so, air can get in, too, and it's your pump, or at least how you're using the pump. My old bike pump would act up like this when I pushed it onto the valve stem too far (presta valves). Could be the case for you, too.

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I believe that the pressure gauge would show that air was entering the tire because it (pressure) would immediately rise but it would rapidly fall unless I kept pumping. It might just be that I didn't properly attach the pump. I will check it out this weekend. Thanks @digijim –  indieDev Apr 24 at 18:29
    
Also check that the valve is still connected to the inner tube. Check for a gash at the base of the valve. This is a big failure point. –  sessyargc.jp Apr 25 at 9:00

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