The best way to paint aluminum siding (and the fastest) is with an airless sprayer. See Spraying Aluminum Siding

If you are not skilled in airless paint application or the situation doesn't lend itself well to airless spraying i.e. there will be overspray problems with the neighbors house, car etc... THEN  you will have to "brush and roll" the aluminum siding

Regardless of the application method, you must first clean the siding. This can be done with a pressure washer or you may clean it by hand.

The Roller
I have had to brush and roll the aluminum siding on a house or two in the past and the best choice for the roller is the mini type of roller.  The mini roller (sometimes called a "pencil" roller) comes in a long (approximately 6" length) thin roller version.  I use the Sherwin Williams covered end  (have roller fabric on the end of the roller as well) mini rollers for this task.






















They are great “clean surface” primers.  They do not wet chalky weathered paint well, so the surface must be clean if you use it as a total house primer on both unweathered and weathered siding.

The Paint
You want high hiding paint without high film build.  High hiding paint:  i.e. "one coat coverage" paint.  You don't want to get up on the ladder and re-roll / re-coat everything if you don't have to.  Use the most expensive, best covering paint you can for this. The extra cost is well worth not having to re-coat everything.  You won't be able to do a one coat job in all circumstances.

If you are changing colors from maroon ( remember the 70's ) to white - you may have to double coat.  Just a note here:  airless spraying will almost always give you one coat hide regardless of color change  - so keep that in mind if you know how to use and operate an airless.

Don't plug the vent holes in the siding
High build paints, multiple coats, and heavy applications will plug up the air ventilation holes / slots on the aluminum siding which allow the siding to vent out from behind the siding.  These holes / slots are located on the bottom edge of each siding strip and on the underside of the soffits.  If you plug the holes, the siding won't vent properly. Don't fill or push paint up into these holes / slots.  The siding needs to breathe.

High build paints will also show roller texture more than lower film build paints. Sherwin Williams Duration is an excellent product for all sorts of exterior paint surfaces and I use it all the time BUT it is a high film build paint (dry film thickness is twice that of a standard exterior paint) and I don't recommend it for aluminum siding repainting.

Application
If your siding is horizontal (as most aluminum siding is),. you will want to roll the siding horizontally, two or three pieces at a time working from one end of the house to the other (or to a breaking point such as a window).  Painting the siding this way will prevent lap marks.  Apply the paint with the covered end roller "bumping" the bottom edge of the siding with the covered end.  Then with a brush wipe the bottom edge of the siding.  Next,  roll the face of the siding again lightly with the roller to smooth out the paint.  Painting the siding this way you will only have an even roller texture "showing". The bottom edge which is "wiped" or "laid off" with a brush will not be noticed.  Just be sure not to plug the ventilation slots / holes with the paint. Don't: apply the paint too thickly on the bottom edge or work the paint into the slots / holes. Do: use a dry brush to pull the paint off or out of the ventilation slots / holes. If you plug a ventilation slot / hole you can open it back up by clearing the paint out with a drill bit or something similar and of the right diameter to push through the holes. If you have slots you can use a small knife perhaps to clear out the paint.

After you complete application of three pieces from one end to the other end of the house - repeat on the next three pieces and continue until the whole side is done.

Do you need to prime?
Weathered aluminum siding that has been cleaned holds paint (quality acrylic latex) very well.  Do a good thorough job on the cleaning and you can paint it directly with latex paint (modified with a tad of Emulsabond)

If the siding is new or glossy,  you will need to prime it to be certain of adhesion.  You may find the siding in protected areas (under the sofits etc.. where the siding is protected from weather) to be glossy.  There are two primers that will stick to glossy aluminum: XIM UMA (Urethane Modified Acrylic) and Zinsser’s 123 Bullseye.  Both of these primers are waterbased  products. 
How to Paint Aluminum Siding - with a Brush & Roller
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