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At some point Alpine switched from openssl to libressl. For some reason this caused an error to appear during last week: Step 17/24 : RUN apk add [...] ---> Running in 52e7e742d29e fetch http://dl-cdn.alpinelinux.org/alpine/v3.7/main/x86_64/APKINDEX.tar.gz fetch http://dl-cdn.alpinelinux.org/alpine/v3.7/community/x86_64/APKINDEX.tar.gz ERROR: unsatisfiable constraints: openssl-dev-1.0.2o-r0: conflicts: libressl-dev-2.6.3-r0[pc:libcrypto=1.0.2o] libressl-dev-2.6.3-r0[pc:libssl=1.0.2o] libressl-dev-2.6.3-r0[pc:openssl=1.0.2o] libressl-dev-2.6.3-r0: conflicts: openssl-dev-1.0.2o-r0[pc:libcrypto=2.6.3] openssl-dev-1.0.2o-r0[pc:libssl=2.6.3] openssl-dev-1.0.2o-r0[pc:openssl=2.6.3] satisfies: postgresql-dev-10.4-r0[libressl-dev] build-dependencies-0: masked in: cache satisfies: world[build-dependencies] Switching to libressl solved that issue but the the cryptography python package build was failing: gcc -Wno-unused-result -Wsign-compare -DNDEBUG -g -fwrapv -O3 -Wall -Wstrict-prototypes -fPIC -I/usr/local/include/python3.5m -c build/temp.linux-x86_64-3.5/_openssl.c -o build/temp.linux-x86_64-3.5/build/temp.linux-x86_64-3.5/_openssl.o In file included from /usr/include/openssl/x509.h:595:0, from /usr/include/openssl/engine.h:96, from build/temp.linux-x86_64-3.5/_openssl.c:567: build/temp.linux-x86_64-3.5/_openssl.c:3467:19: error: expected identifier or '(' before numeric constant static const long X509_V_ERR_HOSTNAME_MISMATCH = 0; ^ build/temp.linux-x86_64-3.5/_openssl.c:3468:19: error: expected identifier or '(' before numeric constant static const long X509_V_ERR_EMAIL_MISMATCH = 0; ^ build/temp.linux-x86_64-3.5/_openssl.c:3469:19: error: expected identifier or '(' before numeric constant static const long X509_V_ERR_IP_ADDRESS_MISMATCH = 0; ^ error: command 'gcc' failed with exit status 1 Upgrading to the latest version solved the issue and the Docker build now works.
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