I have a house built in 1955 with shake siding that has been painted. I had a flag bracket mounted on the front wall with flanged anchors, and it held up for a little over a year (I'd take the flag down during storms), but we recently had an unexpected storm that came through while I was at work, and it ripped the bracket out, anchors and all.
What is the best way to mount a flag bracket on a shake siding wall? Everything I've tried searching tries to redirect me to hanging Christmas lights or mounting things on the roof (because "big G" thinks "shake" is synonymous with "shingle", and of course shingles are more commonly thought of as a roofing material than a siding material; "siding" loves to give me useless information about mounting on vinyl siding, which I suspect is largely not applicable here).
While I plan to replace the siding in another 5-10 years, that's not an option right now.
Best Answer
As noted by other answers, you will do much better by attaching to the supporting members underneath the shingles. The shingles serve their purpose well but are not suited for supporting attached things.
However, this answer differs to focus on the flag mount as part of the issue. They are discussing how to increase the resisting force (which is good and right on target) while this is about how to reduce the applied force.
The problem is that the mount is probably somewhat small and therefore the screws are likely relatively close together, this means that the screws are creating a higher force than if they were further apart. A higher force requires a better attachment point. Reduce the force = reduce the attachment.
I suggest using a 'middle man' approach to deal with both issues, in the form of a wood block. The block would be larger than the flag base to increase the distance between the screws that are attached to your house and therefore reduce how well it must be attached to your house (or increase the strength of the same attachment).
You can size and shape the block if you have basic tools or get a simple 1x4 or other size you like. Often at box stores you can find it in the length that you like or ask to have it cut to length. You might try the trim section of the store for many choices in wood type, color, shape and sizes.
And a wood block would add a very nice finished look. This is a little extra work of course, but a good option to consider.