The proper approach to this is to install vertical strips of wood over the cracks from the outside.
Seal small space between outdoor wooden siding.
In my opinion caulking between the seams in any lapped siding either horizontal or vertical is not good practice but not just because of any potential vapor barrier effect.
Trim boards that sit on top the siding.
Use top quality caulk outdoors where it needs to withstand extreme temperature changes and remain flexible for 30 to 50 years.
Seal small cracks and gaps in your siding under 1 4 inch wide using an acrylic latex caulk.
They also contain mildewcide which helps to prevent mold and mildew growth.
If you prefer weathered cedar s grey color but want a more uniform color than what comes naturally you can seal the cedar using bleaching oils.
Use latex painter s caulk inside of doors and windows or to quickly fill cracks and holes in drywall.
Best for use with drywall wood and masonry.
Use to install wood paneling without nails.
Caulk is a substance designed to seal a joint between two surfaces and to fill small holes.
Paint works well over it.
Sealing for natural weathering.
In the old days the builder would install the trim bring the siding up to it and caulk the corner.
Either way there s at least a half inch space between chimney edge and wood siding.
It needs to move and breathe.
The siding expands and contracts with temperature and humidity.
On most new homes the trim goes up after the siding is installed which creates a large gap that should not be caulked.
Seal a door frame in place and seal the subfloor at the bottom of a door frame.
Simply apply this inexpensive filler into the cracks to seal.
These sealers deeply penetrate the wood and adhere to the porous spaces thus preventing water from penetrating through the material and avoiding decay.
You can choose to use something like 1x2 inch cedar strips.
Possible side effects of sealing cedar siding.
Cover as much of the wood as you can with sealant using a small brush to get into the spaces between panels if the siding is already installed.
Leaving your cedar exposed to the elements for weathering can damage the cedar especially in excessively wet climates.
It looks as though the space has been filled with mortar cement in the past but much of this has fallen out.
At one point it looks like the clapboards may have extended behind the chimney for an inch or so.
Fill in gaps between crown moulding and baseboards.
Think of a wood home as a living thing.
Before caulking joints between dissimilar materials make sure that the manufacturer recommends the caulk for both materials.
It will look like crap and on top of that like you already indicated it will be hard to put in there in the first place.
These include polymer silicone polymer paintable.