I've figured out what I am going to do. I am going to cut the old plumbing off of the overflow box and start over with new bulkheads. The downside is that this will put the tank on hold for at least another week while I wait for parts to arrive in the mail. But it is preferable to trying to fix the problem with silicone and potentially leaving a latent problem waiting to fail. The other plus is that this will allow me to better route the drains into the sump using PVC, which should eliminate some minor kinking I had at the entry to the sump chamber.
My Tank Journal:
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