Questions tagged [openssl]

An open source version of the SSL and TLS protocols.

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How to upgrade OpenSSL in OS X?

Today the heartbleed OpenSSL exploit was announced in the wild, which allows an attacker to surreptitiously detect and steal private server keys (allowing them to MitM and decrypt your encrypted data ...
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56 votes
3 answers
22k views

What versions of OS X are affected by Heartbleed?

What versions of OS X come default with the affected versions of OpenSSL? All Internet traffic right now is clogged with the same generic information in regards to the Heartbleed bug, without any ...
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16 votes
2 answers
6k views

Why is Apple using an older version of OpenSSL?

With the newest OS X Update (10.10.5), Apple is introducing OpenSSL 0.9.8. I browsed through the official OpenSSL page, and there I could get Version 1.0.2. My question is: Why is Apple using an ...
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10 votes
1 answer
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In the light of the FREAK TLS vulnerability, how may I disable insecure cipher suites manually in Safari?

A research group named SMACK has released a vulnerability known as FREAK which can be used for man-in-the-middle (MITM) attack. The vulnerability is due to an old ghost created by USA Government (NSA, ...
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9 votes
3 answers
12k views

How "official" is libressl support in High Sierra?

I am trying to port an OpenSSL-based C program from Linux to macOS, and I would like to use a library for TLS which is officially supported by the OS, because then the OS keeps that library up-to-date ...
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  • 193
8 votes
2 answers
12k views

Ruby 2.0.0 install via RVM: errors surrounding openssl

Using: Mountain Lion 10.8.2, RVM 1.18.15 Having trouble with, apparently, openssl when trying to install Ruby 2.0.0 via RVM: $ rvm install 2.0.0 ... Extracting openssl to /Users/meltemi/.rvm/src/...
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7 votes
1 answer
4k views

How to update Server 5 to TLS 1.2?

In the latest version of Apple's Server app version 5.0.4 running on El Capitan (10.11.2), SSL websites use TLS version 1.0. But, as one Ivan Ristic says, « The bottom line is that TLS 1.0 is insecure ...
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  • 135
7 votes
2 answers
17k views

where is Ruby looking for SSL_CERT_FILE?

I am trying to find out where Ruby expects to find its openssl CA list. My environment is: Mac OS 10.7.5 OpenSSL from homebrew Rbenv from homebrew Ruby 1.9.3, installed using rbenv and CONFIGURE_OPTS=...
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6 votes
2 answers
6k views

homebrew - trouble upgrading openssl?

I'm on osx 10.11. (Background: I'm having trouble getting the system installed Python to use TLS 1.1.) From what I've read I need to use brew to manage Python. But I want to upgrade openssl first ...
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  • 213
4 votes
1 answer
8k views

How do I view or verify signed .mobileconfig files using Terminal?

I need to troubleshoot problems with signed .mobileconfig profiles. How can I show the signature of a these files using Terminal? Is it also possible to verify the certificates that were used to sign ...
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3 votes
3 answers
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how to install stunnel on mountain lion?

I currently bought an Mac, so I'm a noob :). I used to connect to my server using stunnel on windows & ubuntu. I'm also a noob in networking. I check website download section, and there's no mac ...
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  • 141
3 votes
2 answers
6k views

Using Automator or AppleScript to encrypt/decrypt with OpenSSL

I would like to know how to use Automator or AppleScript to create a droplet that would compress/uncompress (tar.gz) and encrypt/decrypt with OpenSSL files and/or directories dropped in it. The ...
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3 votes
2 answers
6k views

OpenSSL not getting linked with homebrew on El Capitan 10.11.6

I am trying to code in C on OS X (El Capitan) and need to use OpenSSL. OS ships with version 0.9.8zh 14 Jan 2016. I used homebrew to upgrade and install openssl (got version 1.0.2h) but am unable to ...
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3 votes
1 answer
2k views

How to upgrade brew ssh after recent client exploit?

I'm running OS X El Capitan 10.11.1 Since the recently discovered SSH client exploit mentioned here I wanted to take action to secure myself. In the process I noticed I'm using Apple's ssh and not ...
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  • 133
3 votes
1 answer
390 views

High Sierra missing openssl manpages

Using the default manpage paths (via /private/etc/man.conf), the openssl(1) and related pages (i.e. x509(1), req(1), ca(1), etc.) are missing. Has anyone discovered if these were placed in a ...
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  • 61
3 votes
1 answer
1k views

Ruby 1.9.3's infamous OS X OpenSSL segfault in http.rb:799

[Post shortened and updated with an answer.] Ruby 1.9.3 compiled on OS X 10.7.4 with MacPorts crashes in my Rails apps when using SSL in http.rb, e.g. when authenticating to Facebook: (facebook) ...
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  • 227
3 votes
2 answers
6k views

'No machine certificates found' when adding machine certificate into VPN

I've 2 certificates, one for user authentication and another for machine authentication. My user authentication includes certificate and private key based on which I've generated pkcs12 file using ...
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2 votes
2 answers
6k views

Using MAMP 3.4, how do I upgrade to Apache 2.4 and OpenSSL 1.0.2 to meet the ATS iOS 9 requirements?

I've just installed MAMP 3.4 on Yosemite but the Apache version inside is still 2.2. Is there a way to upgrade to Apache 2.4? Moreover I have installed through brew openssl 1.0.2 but MAMP Apache still ...
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  • 175
2 votes
1 answer
527 views

Which alternatives to OpenSSL do I have to calculate a SHA-256 hash?

How to calculate SHA-2 hash on a file to generate a 256-bit result (SHA-256)? In the old days we used the openssl tool. I have heard that after terrible security vulnerabilities with openssl, the ...
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2 votes
1 answer
740 views

How do I install OpenSSL in ElCaptain if my HomeBrew it's broken?

After an upgrade from 10.10 to 10.11, my rails environment was broken. I've removed the broken open-source projects/files and now I'm trying to install HomeBrew. But I receive this message: ruby -e ...
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  • 123
2 votes
1 answer
5k views

Server certificates are not properly validated by subversion/openssl

I noticed that the svn cli fails to validate https certificates and always ask for manual validation using the certificate fingerprint: mbp:~ user$ svn co https://svn.mysite.com/svn/testrepo Error ...
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  • 791
2 votes
1 answer
2k views

How do I upgrade my openssl? A symlink isn't working for /usr/local/bin/OpenSSL

I'm having trouble updating my version of openssl so I can get Fastlane working. Can anyone explain where OpenSSL should be, and how different environments hook into it? MACOS:~ lamont$ openssl ...
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2 votes
1 answer
1k views

OpenSSL encryption method doesn't work on El Capitan

The following file encryption method works on OS X Yosemite: Encrypt: openssl enc -aes-256-cbc -salt -in file.zip -out file.zip.enc Decrypt: openssl enc -aes-256-cbc -d -in file.zip.enc -out file....
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2 votes
0 answers
457 views

Using LibreSSL 3.1.1 without messing with the system

I did a brew install of OpenSSL/LibreSSL (3.1.1)... it's located in /usr/local/opt/libressl/bin/openssl I also have the usual macOS Catalina OpenSSL/LibreSSL bin at: /usr/bin/openssl I don't ...
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  • 1,344
2 votes
0 answers
100 views

Encryption after decryption

I have a file encrypted. I want to get the content of the encrypted file and after that I want to encrypt the file with a new key. openssl Type-of-Encryption-used -d -k "key of decription" in- ...
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2 votes
1 answer
2k views

Where to find OpenSSL devel package - can't seem to find it in Brew

I'm trying to install openssl-devel on OS X El Capitan, and I can't seem to find the package on Brew nor the source anywhere online. The application I'm installing (UnrealIRCd) requires both openssl ...
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1 vote
1 answer
3k views

Homebrew: can't remove 'keg-only' OpenSSL application

Given the recent OpenSSL scare I'm trying to clean out older versions from my machines but Homebrew won't let me: $ brew dirty openssl (1.0.1e, 1.0.1f, 1.0.1g) $ brew cleanup openssl Warning: ...
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1 vote
1 answer
1k views

Updating OpenSSL in OSX

I am using 10.9 with Server app 3, and right now i am using an obsolete connection with TLS 1.0, RSA and AES_128CBC with HMAC-SHA1 (that cames by default). While i was trying to upgrade openssl, i ...
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1 vote
1 answer
2k views

How to make a clean install of OpenSSL on El Capitan

I'm afraid I have made a mess with the version (0.9.8zg) of OpenSSL which was installed on my Mac. While I was trying to update it, now I have some error and for some reasons applications like Apache ...
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  • 175
1 vote
3 answers
8k views

Ruby 2.0.0 fails to install because of openssl

I can't install ruby from source, on configuration (./configure) it states Ignore OpenSSL broken by Apple. Please use another openssl. (e.g. using `configure --with-openssl-dir=/path/to/openssl') ...
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1 vote
1 answer
4k views

OpenSSL installation in macOS Mojave 10.14.6?

I am getting odd errors that OpenSSL package has some problems. Earlier I insntalled PyCharm IDE that is built on pyenv environment, it may have somehow broken my OpenSSL. I have tried to install ...
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1 vote
1 answer
717 views

openssl claims to use /private/etc/ssl, but appears not to, What The Heck?

In the course of trying to help a friend with a problem with pip and ssl sites (GitHub issue here), I've become confused about how the High Sierra /usr/bin/openssl finds its certificates. My "keg-...
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1 vote
1 answer
544 views

Install Git on OSX 10.8

ALL, My project is located on GitHub which recently switched to using TLS1.2, which is incompatible with the OpenSSL version OSX 10.8 ships with. So I tried to build Git from sources. I downloaded ...
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  • 867
1 vote
1 answer
212 views

AppleScript - echo into openssl AES encryption - is there a way to crack/snoop thru logs?

Don't know if this question is better off here, or in the Linux world...but I need a decent answer.. :) I am using Applescript to pull data from fields in a spreadsheet or database, shove them ...
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1 vote
1 answer
3k views

Upgrading OpenSSL without linking and workarounds

I am confused by all the posts, questions, answers, dropping symlink, linking, heartbleed bug, etc... that exist on updating your OpenSSL on a Mac. When I run $ openssl version I get OpenSSL 0.9.8zh ...
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  • 148
1 vote
1 answer
3k views

how to make Mac use latest openssl instead of /System/Library/OpenSSL

I just (in June 2016) ran the following instructions to update Openssl (in /usr/local/openssl) on my Mac, but when I check the version, it's showing that I'm using a version built in 2015 (the System/...
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1 vote
2 answers
5k views

OpenSSL 0.9.8zg used by PHP does not support TLSv1.2 or TLSv1.1

As part of the installation a PHP 5.4 cartridge from openshift.com on my Mac with OS X 10.10.5 in the Terminal I noticed a message about it loading OpenSSL 0.9.8 for compatibilty with PHP. Later, ...
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  • 503
1 vote
1 answer
61 views

What determines the relevant version of OpenSSL in a given network connection?

My own system is I think fully "up to date" as far as Apple security updates through the App Store, but the version of OpenSSL installed on my system is 0.9.8zg, a version that was current during the ...
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  • 21
1 vote
1 answer
392 views

Server.app "SSLProtocol: Illegal protocol 'TLSv1.2'"

With following versions installed: OS X 10.11.4 Beta (15E27e) Server.app 5.0.19(15s5065c) Apache/2.4.16 (Unix) OpenSSL/0.9.8zg I get: AH00526: Syntax error on line 581 of /Library/Server/Web/...
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1 vote
1 answer
1k views

How do I determine what TLS ciphers are being used in OSX, Outlook 2011?

I just limited all my SSL ciphers to TLS 1.X and TLS1_RSA_AES and my up-to-date OSX machine is no longer able to connect to the server via Outlook 2011. I can use Safari to connect to the same host,...
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1 vote
1 answer
282 views

Does default e-mail port behave differently than custom?

I'm trying to setup mail on Mavericks to talk directly to my mail server at an ISP. I use the ISP for my mail, but filter it through Gmail and that works. So, here's what I've tried: telnet to port ...
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  • 56
1 vote
2 answers
1k views

Will installation of macports automatically install or update OpenSSL?

I am a mac user and want to stay with the system-provided version of OpenSSL, which is OpenSSL 0.9.8y. I am wondering if installation of macports will automatically update my OpenSSL or install ...
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1 vote
2 answers
1k views

'which openssl' returns nothing when trying to upgrade OpenSSL

I've been working the last day or so to get openssl upgraded on my machine. I've followed the answers here and here and now I've got some pretty funny results. When I type which openssl I get no ...
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1 vote
0 answers
425 views

Catalina and pyenv install python versions fine, but anything needing ssl fails

I seek to use pyenv instead of manually installing an official python release. My goal is to run the included script titled “Install Certificates.command”. My assessment of the situation is pyenv is ...
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1 vote
0 answers
175 views

Mac M1 SQL Server SQLSrv OpenSSL library could not be loaded, make sure OpenSSL 1.0 or 1.1 is installed

I just bought a M1 Mac mini running Big Sur 11.6, I've installed PHP 7.3, msodbcsql17, mssql-tools, sqlsrv and pdo_sqlsrv. But when I try to connect using sqlsrv, the following error happens [...
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  • 11
1 vote
1 answer
417 views

Updating path openssl keeps using wrong path

I had to downgrade openssl version for mysql. But when I ran openssl version I still got the wrong version. So I checked which openssl and I saw that it's using from anaconda: (base) ➜ ~ which ...
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  • 113
1 vote
0 answers
64 views

Why do browsers still not trust my internal sites even after installing the CA chain?

I host several web services on my internal network and have created TLS certificates for each of them, all signed by my home-baked OpenSSL certificate authority. I've imported the CA certificates into ...
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1 vote
0 answers
304 views

Segmentation Fault Generating Self Signed Certificate using OpenSSL on OS X

I am trying trying to generate a private key and a self signed certificate from my terminal on OS X El Capitan (10.11.1) using the commands below: openssl genrsa 1024 > private.key openssl req -...
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  • 111
1 vote
0 answers
528 views

Cannot verify Google's SSL certificate with openssl

When checking Google's certificate with OpenSSL I get $ echo 'Q' | /usr/bin/openssl s_client -connect www.google.com:443 -servername www.google.com -verify 6 > /dev/null verify depth is 6 depth=2 ...
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  • 8,212
1 vote
2 answers
1k views

Openssl on mac -In is not working

I am follow a tutorial guide from this link http://osxdaily.com/2012/01/30/encrypt-and-decrypt-files-with-openssl/ to try to produce -sha256 hash from an input file but when i type openssl dgst -...
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  • 13