If the tube that you are using has a straight valve it can be really difficult to get the pump all the way on. I would encourage getting a tube that has a bent stem. Also, I would highly recommend getting a bike pump with a pressure gauge from you local bike store. The pump should only cost you about $25 and will save you a lot of time and hassle. phil&teds tires are finicky and it's really easy to over inflate the tires.
For phil&teds replacement tubes you should check out Little Mountain Outfitters. They sell the right size tubes with a bent stem.
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The Bugaboo pump is a plastic joke and a bad one at that. Most Bugaboo's have the same tyre valve as a car and a car foot pump from your auto shop or department store will be cheaper and faster. If you want a more portable pump check out your local bike shop they have far better ones available. Very old Bugaboos have the smaller bicycle valve the newest Bugaboo's now have foam filled tires. Once you've pumped it up check for leaks, just unclip the wheel and stick it in a tub of water. If you have bubbles you need to fix the tube,
Look on the sidewall of your tire and see what it is rated for. Also, do not go to a gas station to fill it up, go to a bike shop and ask them or buy a bicycle pump with a gauge. Always make sure that your tire is seated on the rim evenly or you will pinch the tube and it will blow up. Car tires have more volume so that is why you cannot use the same air pressure device. Your tire will say 90-120 lbs more that likely but your tires is not that big around.
Look at your tire,on the side wall it will tell you what amount to put in. Do not fill at a gas station, it is made for a car tire, and will blow the tire off the rim. Buy a tire gauge and a decent pump, and watch the bead on the tire to seat evenly as you add air.
Replacement tube may be more beneficial even though the fix/patch may be cheaper. If you live in an area that have varying climate, the patch along with the repaired tube can expand and contract and may cause small leak if not repaired properly.
Otherwise I would get the right size tube, most jogging strollers are either 12" or 16" tube inside and can be bought from your local bicycle store. With that, you'll need bicycle tire levers which can also be bought at the bike shop. Just about any type of tire levers will do. Of course I'm sure your bike shop can do this for you to possibly for free with a purchase of replacement tube!
gas stations or tire places can often help fix a bicycle tire-- why not a stroller tire? shoudlnt cost more than 5-10 bucks.
if just a slow leak, you can also try a can of fix-a-flat from the auto parts store-- pump it into your tire when somewhat deflated, walk it around to let the inside get coated with the material, and then inflate it to proper levels.
The tyre and inner tube can be removed in the same way as a standard bicycle tyre, you can google how to remove a tyre to get some more advise.
Once you have removed the inner tube, place it in a bowl of water and try to inflate it with the pump. If you see any bubbles escaping from the tube, you have a puncture and will need to repair, again, additional advise can be found online or talk with your local bike shop for direct advise on how to do this.
If you see no bubbles you need to check that air is not escaping from the pump, if its broken then it will just vent the air as soon as you put it in.