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We were able to resolve this by copying over raw /usr/share/ca-certificates/ from the builder. We used to run update-ca-certificates in the builder (jammy) and then copy over everything in '/etc/ssl/certs' which includes the ca-certificate.crt file. For some reason in this case, the underlying SSL implementation of the httplib also wanted the raw .pem files of the root CAs (we still dont know why)

tldr;

In the jammy builder:

RUN update-ca-certificates

In the runtime chiseled image:

COPY --from=builder /usr/share/ca-certificates/ /usr/share/ca-certificates/
COPY --from=builder /usr/local/share/ca-certificates/ /usr/local/share/ca-certificates/
COPY --from=builder /etc/ssl/certs /etc/ssl/certs

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@jaskaransinghdr6j
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@richlander
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@jaskaransinghdr6j
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@richlander
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