Dyld: Library Not Loaded: /Usr/Local/Opt/Openssl/Lib/Libssl.1.0.0. Dylib

December 2020 This thread has many answers, but none worked for me.
The top answer also suggests a downgrade:

brew switch ... throws Calling brew switch is disabled!

this worked for me:

brew install rbenv/tap/openssl@1.0
ln -sfn /usr/local/Cellar/openssl@1.0/1.0.2t /usr/local/opt/openssl

found here:
(I need to run old mongodb 3.4 on OSX 10.13.x)

brew switch openssl 1.0.2s

worked for me on "macOS Mojave", "version 10.14.6".

Try to use install_name_tool:

sudo install_name_tool -change /usr/local/opt/openssl/lib/libssl.1.0.0.dylib /usr/local/opt/openssl/lib/libssl.1.1.dylib $(which vapor)
sudo install_name_tool -change /usr/local/opt/openssl/lib/libcrypto.1.0.0.dylib /usr/local/opt/openssl/lib/libcrypto.1.1.dylib $(which vapor)

In my case it start working when I used install_name_tool. The order of the parameter is following: old value (incorrect), then new value (where you have your openssl) and the path to vapor (which can be easily get by $(which vapor).

first, list the details of the installed openssl version(or other programs) by:

$ls -al /usr/local/Cellar/openssl*
/usr/local/Cellar/openssl:
total 0
drwxr-xr-x    3 mba  staff    96 Nov 30 17:18 .
drwxrwxr-x  170 mba  admin  5440 Apr  8 02:03 ..
drwxr-xr-x   13 mba  staff   416 Nov 21 03:13 1.0.2t

/usr/local/Cellar/openssl@1.1:
total 0
drwxr-xr-x    4 mba  staff   128 Apr  7 18:35 .
drwxrwxr-x  170 mba  admin  5440 Apr  8 02:03 ..
drwxr-xr-x   14 mba  staff   448 Oct  1  2019 1.1.1d
drwxr-xr-x   14 mba  staff   448 Apr  7 18:35 1.1.1f

as above output, there are only one "right" versions "openssl" in my mac. then, switch to it:

$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

For MacOS 10.15 Catalina try to install the previous openssl:

brew update && brew upgrade
brew uninstall --ignore-dependencies openssl
brew install 

brew switch openssl 1.0.2q

MacOs Catalina Version 10.15 worked for me

I had the same problem. I solved it by running these 2 commands:

brew uninstall vapor
brew install vapor/tap/vapor

It worked.

brew switch openssl 1.0.2r

it work for me,macOS Mojave, Version 10.14.6

brew switch openssl 1.0.2t

catalina this is ok.

This is the only thing that worked for me (OSX Catalina 10.15.7)

1- Download the file:

wget 

2 - Run brew with the file downloaded:

brew install openssl.rb

This worked for me on my mac

brew switch openssl 1.0.2n

i'll throw in my 2 cents because i didn't see an answer that resolved my issue.

my particular use case, relates to starting a legacy rails application using ruby 2.6.3 with postgres 10.x series.

• i'm running macOS 10.13.x high sierra
• i update brew almost on a daily basis, and the version of openssl i have is 1.1

haven't started the rails app in several months, needed to perform some maintenance on the app today and, got some lovely ❤ error messages below,

9): Library not loaded: /usr/local/opt/openssl/lib/libssl.1.0.0.dylib (LoadError)
  Referenced from: /usr/local/opt/postgresql/lib/libpq.5.dylib

echo "and"

9): Library not loaded: /usr/local/opt/openssl/lib/libcrypto.1.0.0.dylib (LoadError)
  Referenced from: /usr/local/opt/postgresql/lib/libpq.5.dylib
  Reason: image not found -

the quickest way to work around my particular issue was to create a smylink from the current,

libssl.1.1.dylib
libcrypto.1.1.dylib

create 2 symlinks

cd /usr/local/opt/openssl/lib/
ln -sf libcrypto.1.1.dylib libcrypto.1.0.0.dylib
ln -sf libssl.1.1.dylib libssl.1.0.0.dylib

paths and version numbers are obviously going to change over time so pay attention to the path and version numbers while creating the above symlinks. after the symlinks were created, i am able to start my rails app.

cheers

leaving this here for future me 👴🏼

brew reinstall openssl

It automatically updates mysql server compatible with openssl. I tried many things, but only this worked for me.

I had a similar issue and running the command below fixed the error for me:

brew update && brew upgrade

I had to downgrade OpenSSL in this way:

brew uninstall --ignore-dependencies openssl
brew install 

It was the only solution that worked for me.

If anyone is coming for openssl@1.1 issue in MacOS Big Sur,(i.e. Library not loaded: /usr/local/opt/openssl@1.1/lib/libssl.1.1.dylib, here's what solved it for me-

brew install openssl@1.1
ln -s $(brew --prefix)/opt/openssl/lib/libssl.1.1.dylib /usr/local/lib/
ln -s $(brew --prefix)/opt/openssl/lib/libcrypto.1.1.dylib /usr/local/lib

A simple brew update && brew upgrade did the trick for me

Proposing brew update && brew upgrade as the solution is not a good answer and, as this error appears in most of the cases due the execution of this...

Switch to the previous version you were using with only: brew switch openssl XXX and that's it.

Mehn this is me in July 7, 2020, after facing this error for 4 hours. This is the only command that worked for me:

brew update && brew upgrade

Had this issue when trying to use LastPass CLI via Alfred on my Catalina install.

brew update && brew upgrade fixed the issue.

This is a much better optin than downgrading openssl.

This worked for me:

brew uninstall openssl
brew tap-new $USER/old-openssl
brew extract --version=1.0.2t openssl $USER/old-openssl
brew install openssl@1.0.2t

Source:

If you are using ruby-2.7.0 on MacOS Catalina 10.15

$ brew reinstall openssl@1.1

or

$ rvm reinstall 2.7.0
$ brew tap --repair
$ brew doctor

This might be a problem because of having the older version of brew and installed byobu which require new dependency in order to solve this problem run the following command

brew update && brew upgrade
brew uninstall openssl; brew uninstall openssl; brew install 

Explanation an solution: It seems that you're required to install older openssl version that is no longer exist on current brew repository ( 1.0.2t version ) . In order to solve it you should create a tap and extract an older version ( looking through repository history), after new installation create a link to this version and you're linked to the right version.

brew uninstall --ignore-dependencies openssl
brew tap-new $USER/old-openssl
brew extract --version=1.0.2t openssl $USER/old-openssl
brew install openssl@1.0.2t
ln -s /usr/local/Cellar/openssl@1.0.2t/1.0.2t /usr/local/opt/openssl

Documentation :

Taps (Third-Party Repositories) brew tap adds more repositories to the list of formulae that brew tracks, updates, and installs from. By default, tap assumes that the repositories come from GitHub, but the command isn’t limited to any one location.

 tap-new [options] user/repo
      Generate the template files for a new tap.
      
 --no-git: Don’t initialize a git repository for the tap.
 --pull-label: Label name for pull requests ready to be pulled (default pr-pull).
 --branch: Initialize git repository with the specified branch name (default main).

extract [options] formula tap Look through repository history to find the most recent version of formula and create a copy in tap/Formula/. If the tap is not installed yet, attempt to install/clone the tap before continuing. To extract a formula from a tap that is not homebrew/core use its fully-qualified form of user/repo/formula.

extract [options] package user/repo
--version: Extract the specified version of formula instead of the most recent.
-f, --force: Overwrite the destination formula if it already exists.

The above answers didn't work for me. I am on Big Sur 11.6 with Xcode 12.5.1 and the brew keeps giving me an error saying my command line tools are outdated. First step is to update Xcode to 13.0. Restart the machine, and then run the

brew install openssl@1.1

Restart the terminal and now re-run the command which was giving the following error:

dyld: Library not loaded: /usr/local/opt/openssl@1.1/lib/libssl.1.1.dylib

Everything should work fine now, and you will not see the error message anymore.

I had a similar issue and based on this and other comments here's what happened and worked:

➜ brew update && brew upgrade && brew install openssl
remote: Repository not found.
fatal: repository ' not found
Error: homebrew/homebrew-dupes does not exist! Run `brew untap homebrew/homebrew-dupes` to remove it.
...
➜ brew untap homebrew/homebrew-dupes
➜ brew update && brew upgrade && brew install openssl

This was after working on it for hours, but first time I saw the homebrew-dupes. Not sure how Homebrew knew what to install, but it seemed to install everything from scratch. macOS Catalina, zsh. I think the initial problem came because of Catalina

The error I was getting was:

dlopen(/Users/gscar/.gem/ruby/2.7.0/gems/pg-1.2.2/lib/pg_ext.bundle, 9): Library not loaded: /usr/local/opt/openssl/lib/libssl.1.0.0.dylib (LoadError)
  Referenced from: /usr/local/opt/postgresql/lib/libpq.5.dylib
  Reason: image not found - /Users/gscar/.gem/ruby/2.7.0/gems/pg-1.2.2/lib/pg_ext.bundle

If you don't have Homebrew or don't know what is it

/usr/bin/ruby -e "$(curl -fsSL )"
brew update && brew upgrade
brew uninstall openssl; brew uninstall openssl; brew install 

Or if you already have Homebrew installed

brew update && brew upgrade
brew uninstall openssl; brew uninstall openssl; brew install 

This works for me on Mac 10.15

Above solution didn't work for me.

First run brew doctor. if you see something like

Error: unknown or unsupported macOS version: :mountain_lion

then there are some outdated packages which needs to be removed, mine was
mongodb.

It could be python@2, node@6 or some other package.

uninstall those packages brew uninstall [name] then run brew doctor to verify if everything is ok. Then you can reinstall those packages again after brew update && brew upgrade.

My recommendation is to never lower your openssl lib version for the sake of getting your build to work. Better to download the source code of the required lib and build it against the openssl version you have on your localhost.

I came across this posting while going through the same issue but was not comfortable lowering the openssl version come what may. Finally took the source code and build the app and it worked. I dont know why devs have their old versions of openssl on their boxes and which they build the dist packages and publish against those old version.