Label the canisters with the name of the pollen parent. Do not put a lid on the canister so they will dry out and not get moldy. After a few hours (on some rose varieties), or the next day (on other varieties), the pollen sacs will burst open, thereby releasing the pollen. Sometimes you will need to shake the canister so that the rose pollen will release from the pollen sacs. The black film canisters make it easy for you to see the pollen, which looks like a fine yellow powder. The pollen will stay fresh for about two weeks.   
When pruning, be judicious. If you prune too hard in autumn, plants can be damaged beyond recovery. Instead, wait until spring, when plants begin to leaf out for the new season. (Roses are often not the earliest plants in the garden to respond to spring’s warming temperatures, so be patient.) Give the plant time to show its leaf buds then prune above that level.
Select the pollen parent flower. Remove the petals and harvest the stamens -- the male flower part that has the pollen -- as in the previous two steps. Check the stamens immediately to see if they are producing fluffy, mature, yellow pollen. If so, proceed to pollination. If not, look at stamens in the vials daily. Use them for pollination when mature pollen is coming loose from the stamens.
So grandma had the right idea in the first place, and she really did know what she was doing. It has always been fun to start roses from cuttings. Some people get their kicks by going "rose rustling" in the deserted cemeteries of old and forgotten mining towns. Others just take a twig from their favorite rose and stick it into the ground in their backyard. There is nothing complicated nor scientific about taking cuttings of roses and rooting them to "start" a new plant. There are various ways of taking rose cuttings, so let's tell you how.
Allow rose hips to develop by leaving dead flowers on the plant. The flowers are typically pollinated by insects, or pollinate themselves in some varieties, so there is no need to pollinate by hand unless you are breeding specific plants together. Leave the flowers on the rose plant without cutting them. After they wither, small fruits known as rose hips will develop in their place.
There will be disappointments along the way, when many rose seeds fail to germinate, or perhaps they do germinate, only to die several weeks later from damp-off disease. Sometimes a rose seedling will turn out to be as ugly as sin, or very sickly, and you will reluctantly have to throw it away. Other times they will be just ho-hum, or look too much like its parent, and therefore have no value. But, just when you don't expect it, you might discover that one of your rose seedlings turns out to be very special.   
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