In the image to the right, you see hikers approaching the Old Army Pass well above Timberline. The trail from the Cottonwood Lakes Basin to the top of Old Army Pass is unmaintained, and can get a little rough here and there, but overall, it is in good condition.
In early season, snow can present a problem, and crampons and ice ax will be necessary if snow and ice cover the trail. But as the year wears on, the snow and ice melt out, and most folks have no problem reaching the pass using this trail.
We went to the top of Mt Langley in August of 2006, and as you can see, there is still some snow on the trail. 2006 was a particularly heavy snow year, so conditions can vary greatly from year to year. But as stated above, June and especially July provide a great mix of good trail conditions along with plenty of water and greenery.