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The error in the log you attached is: :info:build dyld: Library not loaded: /opt/local/lib/libcrypto.1.0.0.dylib :info:build Referenced from: /opt/local/lib/libxar.1.dylib :info:build Reason: image not found :info:build fatal error: otool: fatal error in /opt/local/bin/llvm-objdump-mp-7.0 If you were using the current version of /opt/local/lib/libxar.1.dylib (which is provided by the xar port), it would have been linked with /opt/local/lib/libcrypto.1.1.dylib, not /opt/local/lib/libcrypto.1.0.0.dylib. This suggests you haven't followed the usual migration steps, which would have you uninstall all your ports before trying to install new ones. I myself often upgrade this way, but I'm comfortable reading the failure logs and figuring out what I need to do to proceed. In this case, if you want to continue to try to upgrade your ports piecemeal, what you need to do is upgrade xar first. But you may run into further problems after that. If you want to avoid that, follow the migration instructions. https://trac.macports.org/wiki/Migration
