Homebrew refusing to link OpenSSL

Question

I m on  OSX 10 11 6  Homebrew version 0 9 9m OpenSSL 0 9 8zg 14 July 2015  I m trying to play with with dotnetcore and by following their instructions    I ve upgraded installed the latest version of openssl    gt  brew install openssl    gt  Downloading https   homebrew bintray com bottles openssl-1 0 2h 1 el capitan bottle tar gz Already downloaded   Users administrator Library Caches Homebrew openssl-1 0 2h 1 el capitan bottle tar gz    gt  Pouring openssl-1 0 2h 1 el capitan bottle tar gz    gt  Caveats A CA file has been bootstrapped using certificates from the system keychain  To add additional certificates  place  pem files in    usr local etc openssl certs  and run    usr local opt openssl bin c rehash  This formula is keg-only  which means it was not symlinked into  usr local   Apple has deprecated use of OpenSSL in favor of its own TLS and crypto libraries  Generally there are no consequences of this for you  If you build your own software and it requires this formula  you ll need to add to your build variables       LDFLAGS   -L usr local opt openssl lib     CPPFLAGS  -I usr local opt openssl include   But when I try to link openssl I continue to run into this linking error    gt  brew link --force openssl Warning  Refusing to link  openssl Linking keg-only OpenSSL means you may end up linking against the insecure  deprecated system version while using the headers from the Homebrew version  Instead  pass the full include library paths to your compiler e g     -I usr local opt openssl include -L usr local opt openssl lib   The option to include compiler flags doesn t make sense to me  since I m not compiling these libraries that I m dependent on    EDIT dotnetcore has updated their instructions   brew update     brew install openssl     ln -s  usr local opt openssl lib libcrypto 1 0 0 dylib  usr local lib      ln -s  usr local opt openssl lib libssl 1 0 0 dylib  usr local lib

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export https proxy http   127 0 0 1 1087 http proxy http   127 0 0 1 1087 all proxy socks5   127 0 0 1 1080   works for me  and I think it can solve all the problems like  Failed to connect to raw githubusercontent com port 443  Connection refused

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None of these solutions worked for me on OS X El Capitan 10 11 6  Probably because OS X has a native version of openssl that it believes is superior  and as such  does not like tampering  So  I took the high road and started fresh     Manually install and symlink cd  usr local src     If you re getting  quot No such file or directory quot   make it  cd  usr local  amp  amp  mkdir src  amp  amp  cd src   Download openssl  curl --remote-name https   www openssl org source openssl-1 0 2h tar gz  Extract and cd in  tar -xzvf openssl-1 0 2h tar gz cd openssl-1 0 2h  Compile and install    configure darwin64-x86 64-cc --prefix  usr local openssl-1 0 2h shared make depend make make install  Now symlink OS X s openssl to your new and updated openssl  ln -s  usr local openssl-1 0 2h bin openssl  usr local bin openssl  Close terminal  open a new session   and verify OS X is using your new openssl  openssl version -a

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After trying everything I could find and nothing worked  I just tried this   touch    bash profile  open    bash profile   Inside the file added this line   export PATH   PATH  usr local Cellar openssl 1 0 2j bin openssl    now it works     Jorns-iMac   jorn  openssl version -a OpenSSL 1 0 2j  26 Sep 2016 built on  reproducible build  date unspecified   blah blah OPENSSLDIR    usr local etc openssl   Jorns-iMac   jorn  which openssl  usr local opt openssl bin openssl

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If migrating your mac breaks homebrew   I migrated my mac  and it unlinked all my homebrew installs - including OpenSSL  This broke gem install  which is how I first noticed the problem and started trying to repair this   After a million solutions  when migrating to OSX Sierra - 10 12 5   the solution ended up being comically simple   brew reinstall ruby brew reinstall openssl

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Note  this no longer works due to https   github com Homebrew brew pull 612  I had the same problem today  I uninstalled  unbrewed    openssl 1 0 2 and installed 1 0 1 also with homebrew  Dotnet new restore run then worked fine   Install openssl 101  brew install homebrew versions openssl101  Linking  brew link --force homebrew versions openssl101

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The solution might be updating some tools  Here s my scenario from 2020 with Ruby and Python  I needed to install Python 3 on Mac and things escalated  In the end  updating homebrew  node and python lead to the problem with openssl  I did not have openssl 1 0 anymore  so I couldn t  quot brew switch quot  to it  So what was still trying to use that old 1 0 version  It tuned out it was Ruby 2 5 5  So I just installed Ruby 2 5 8 and removed the old one  Other things you can try if this is not enough  Use rbenv and pyenv  Clean up gems and formulas  Update homebrew  node  yarn  Upgrade bundler  Make sure your  bash profile  or equivalent  is set up according to each tool s instructions  Reopen the terminal

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I had the same problem while trying to install newer version of ruby 2 6 5  https   github com kelaberetiv TagUI issues 86 helps me to solve the problem  This if for macOS catalina Version 10 15 1  Basically  I did update and upgrade homebrew and install openssl and install ruby   brew update  amp  amp  brew upgrade brew install openssl   Then create these 2 symlinks   ln -s  usr local opt openssl lib libcrypto 1 0 0 dylib  usr local lib  ln -s  usr local opt openssl lib libssl 1 0 0 dylib  usr local lib    then installed ruby 2 6 5

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Just execute brew info openssland read the information where it says      If you need to have this software first in your PATH run  echo  export PATH   usr local opt openssl bin  PATH    gt  gt     bash profile

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As the update to the other answer suggests  the workaround of installing the old openssl101 brew will no longer work   For a right-now workaround  see this comment on dotnet cli 3964   The most relevant part of the issue copied here      I looked into the other option that was suggested for setting the rpath on the library  I think the following is a better solution that will only effect this specific library       sudo install name tool -add rpath  usr local opt openssl lib  usr local share dotnet shared Microsoft NETCore App 1 0 0 System Security Cryptography Native dylib      and or if you have NETCore 1 0 1 installed perform the same command for 1 0 1 as well       sudo install name tool -add rpath  usr local opt openssl lib  usr local share dotnet shared Microsoft NETCore App 1 0 1 System Security Cryptography Native dylib      In effect  rather than telling the operating system to always use the homebrew version of SSL and potentially causing something to break  we re telling dotnet how to find the correct library    Also importantly  it looks like Microsoft are aware of the issue and and have both a  a somewhat immediate plan to mitigate as well as b  a long-term solution  probaby bundling OpenSSL with dotnet    Another thing to note   usr local opt openssl lib is where the brew is linked by default   13 22   ls -l  usr local opt openssl lrwxr-xr-x  1 ben  admin  26 May 15 14 22  usr local opt openssl - gt     Cellar openssl 1 0 2h 1   If for whatever reason you install the brew and link it in a different location  then that path is the one you should use as an rpath   Once you ve update the rpath of the System Security Cryptography Native dylib libray  you ll need to restart your interactive session  i e   close your console and start another one

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The solution above from edwardthesecond worked for me too on Sierra   brew install openssl  cd  usr local include   ln -s    opt openssl include openssl     configure  amp  amp  make   Other steps I did before were    installing openssl via brew  brew install openssl  adding openssl to the path as suggested by homebrew  brew info openssl echo  export PATH   usr local opt openssl bin  PATH    gt  gt     bash profile

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By default  homebrew gave me OpenSSL version 1 1 and I was looking for version 1 0 instead  This worked for me    To install version 1 0   brew install https   github com tebelorg Tump releases download v1 0 0 openssl rb   Then I tried to symlink my way through it but it gave me the following error   ln -s  usr local Cellar openssl 1 0 2t include openssl  usr bin openssl ln   usr bin openssl  Operation not permitted   Finally linked openssl to point to 1 0 version using brew switch command   brew switch openssl 1 0 2t Cleaning  usr local Cellar openssl 1 0 2t Opt link created for  usr local Cellar openssl 1 0 2t

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I have a similar case  I need to install openssl via brew and then use pip to install mitmproxy  I get the same complaint from brew link --force  Following is the solution I reached   without force link by brew   LDFLAGS -L usr local opt openssl lib  CPPFLAGS -I usr local opt openssl include PKG CONFIG PATH  usr local opt openssl lib pkgconfig  pip install mitmproxy   This does not address the question straightforwardly  I leave the one-liner in case anyone uses pip and requires the openssl lib   Note  the  usr local opt openssl lib paths are obtained by brew info openssl

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This is what worked for me   brew update brew install openssl ln -s  usr local opt openssl lib libcrypto 1 0 0 dylib  usr local lib  ln -s  usr local opt openssl lib libssl 1 0 0 dylib  usr local lib  ln -s  usr local Cellar openssl 1 0 2j bin openssl  usr local bin openssl   Thanks to  dorlandode on this thread https   github com Homebrew brew pull 597   NB  I only used this as a temporary fix until I could spend time correctly installing Openssl again from scratch  As I remember I spent best part of a day debugging and having issues before I realised the best way was to manually install the certs I needed one by one  Please read the link in  bouke s comment before attempting this

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This worked for me    brew install openssl  cd  usr local include   ln -s    opt openssl include openssl

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for me this is what worked     I edited the   bash profile and added below command  export PATH   usr local opt openssl bin  PATH

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