Why is this new external wood paint looking so bad already?

It depends on the location of the crack. If it's at a normal joint and straight, silicone will not look out of place and needn't be painted. I had partial success with painting non-paint-able silicon. If the primer is a good glue, you could have some success.
 
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Is that the sikaflex EBT? I have a tube but it doesn't seem to advertise as being paintable. Although it's white and so is my paintwork...

Yes, it can be painted but you need to use water based primer first. If you don't, the OB paint will be tacky for weeks.

I have painted over it in the past but, strangely, they say it cannot be over painted.

https://www.everbuild.co.uk/wp-content/uploads/2014/04/SikaflexEBTColours-V1.1.pdf

In spite of the above, I would be happy to use it. It is quite sticky, a fellow forum member kindly recommended dipping my finger in white spirit.
 

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