Cannot remove passphrase from private key with openssl - heroku

All the web pages our there suggest removing the passphrase from a private key file by running a simple openssl command. But when I run the command it does not ask for my current passphrase or remove it from the newly created one.
Here is what I run:
MacBookPro:simplegym harris$ openssl version
OpenSSL 1.0.1e 11 Feb 2013
MacBookPro:simplegym harris$ openssl rsa -in KeyWithPassphrase.key -out KeyWithoutPassphrase.key
writing RSA key
MacBookPro:simplegym harris$
Unfortunately the KeyWithoutPassphrase.key that is generated DOES have a passphrase?
This is BIG issue for me because Heroku will not accept a private key with a passphrase in order to configure an SSL certificate.
Ideas???
Thanks for any help,
--harris

Related

Import pfx to IIS Windows server 2016 - The specified network password is not correct

I am using openssl to convert the cert bought from Godaddy for using IIS Windows 2016. Command I used to convert is the following, I press Enter for no password. I also tried input a simple and complex password, still got the same error.
openssl pkcs12 -export -out website.pfx -inkey private.key -in a01f36fe692456.crt -certfile gd_bundle-g2-g1.crt
It comes with "The specified network password is not correct" when importing to IIS on Windows Server 2016, to troubleshoot, I tried the same import, but it can import to Windows server 2019. Wondering how to generate a pfx file for Windows 2016, IIS v10? Thanks
I've got it working with IIS using openssl to create the file; It works if you import to your local user certificate store then export it, I compared the exported pfx file to the openssl pfx file using
openssl pkcs12 -in website.pfx -info
The MAC is sha256 on the openssl version, compared to SHA1 on the export version so I added -macalg SHA1 to the openssl command.
The PKCS7 Data for the private key is PBES2, PBKDF2, AES-256-CBC on the openssl version, compared to pbeWithSHA1And3-KeyTripleDES-CBC on the export version so I added -keypbe PBE-SHA1-3DES to the openssl command.
The same for the PKCS7 Encrypted data for the certificates, so I added -certpbe PBE-SHA1-3DES to the openssl command as well.
The final command I ran to get a successful file that will import to IIS is
openssl pkcs12 -macalg SHA1 -keypbe PBE-SHA1-3DES -certpbe PBE-SHA1-3DES -export -out website.pfx -inkey private.key -in a01f36fe692456.crt -certfile gd_bundle-g2-g1.crt
I run into the same problem while i was trying to import the pfx file on my server (WS 2016 Standard) and none of the options above worked for me.
I even tried to generate the pfx again using the certificate and the private key, but it would still refuse the password.
So i'm adding what worked for me for completness sake.
To be able to import the certificate on the server i had to :
Import into my local machine (W10 Enterprise), I marked it as exportable.
Exported the pfx from my local machine .
Import the exported pfx file in the server (WS 2016 Standard)
It seems to be a compatibility issue with windows but im not sure what issue really is and how the import and export solves it.
This works for me to but this is not at all a correct solution i recon...
3des-sha1 have been hacked for ages...
Taking a look at the pfx files vs.
created with this openssl command:
MAC: sha1, Iteration 2048
MAC length: 20, salt length: 8
PKCS7 Encrypted data: pbeWithSHA1And3-KeyTripleDES-CBC, Iteration 2048
Shrouded Keybag: pbeWithSHA1And3-KeyTripleDES-CBC, Iteration 2048
Orgininal pfx which doesn't work:
MAC: sha256, Iteration 2048
MAC length: 32, salt length: 8
PKCS7 Encrypted data: PBES2, PBKDF2, AES-256-CBC, Iteration 2048, PRF hmacWithSHA256
Shrouded Keybag: PBES2, PBKDF2, AES-256-CBC, Iteration 2048, PRF hmacWithSHA256
How can i get the normal crypto with sha256 imported..

How to use a TLS client certificate with a RubyGems registry?

I have an internal RubyGems registry from which I want to download some Gems. The registry is protected and requires a valid TLS Client Certificate.
I am able to reach the registry in Chrome (imported the certificate bundle into Chrome), but I am not able to do it with Bundler.
The documentation says ssl_client_cert has to be:
Path to a designated file containing a X.509 client certificate and key in PEM format.
I get the following error when using the certificate provided:
either PUB key nor PRIV key: nested asn1 error
How do I assemble my certificate and key?
I finally found how to assemble the files:
# Concatenate the key and the certificate
openssl rsa -in key.pem > ruby-bundler-cert.pem
openssl x509 -in cert.pem >> ruby-bundler-cert.pem
# Tell bundler to use the file
bundle config ssl_client_cert ~/certs/ruby-bundler-cert.pem
Did you think this was enough? No! You also need to specify this value somewhere else: in your ~/.gemrc file.
:ssl_client_cert: "/full/path/to/the/certs/ruby-bundler-cert.pem"
Hope this will help other people.

Can't load TLS/SSL certificate to FileZilla Server - "no start line" error

I just created a TLS/SSL certificate (in Windows) with the following openssl command:
openssl req -x509 -newkey rsa:4096 -keyout key.pem -out cert.pem -days 365
After this, I tried to load it in the FileZilla server but it gives me an error that says:
Could not load certificate file: error:0906D06C:PEM
routines:PEM_read_bio:no start line(0)
I already verified that the two certificates (key and crs) don't contain any blank spaces, and don't have ^M at the end of any line. What could be the cause of this?
I would guess that you have select the certificate file (cert.pem) as a Private key file and the private key file (key.pem) as a Certificate file.
It should be:
Private key file = key.pem
Certificate file = cert.pem
Also the key have to be generated without a passphrase, otherwise you get
Could not load key file: error:0907B068:PEM
routines:PEM_READ_BIO_PRIVATEKEY:bad password read (0)
So you need to add -nodes to the openssl command-line.
Though why do you even use openssl to generate the certificate? FileZilla Server interface has Generate new certificate wizard.

Convert crt to pem with private key

I really didnt want to ask this but i cannot find a solid answer online that i understand. I am not good at networking/IIS/certificates and need some help. I have a CRT file generated from godaddy, i have it installed on the server but need to create a PEM file with a private key and the certificate inside it so i can do a key exchange. I have a DER file created, then a PEM file created using OpenSSL with the certificate in it. My question is how do i create a private key and then place it inside the PEM file? Im sorry if this doesnt make any sense, if so please just let me know i am on the wrong track. My goal is to set up an FTP key exchange and this is what a client of mine is requesting. the cert is in 2048 bit RSA format.
How do you create private key of the certificate you already have? You must have private key to sign the certificate signing request (CSR). You can export this private key into any format (provided that it is marked as exportable) you want.
If you can export the private key then one solution is that you can concatenate your file with private key and public key if it is supported by your application.
Another way is to combine them into pfx or PKCS #12 file.
You can see the about openssl pkcs12 here.
Turns out this is what i needed, thanks for the assistance.
openssl pkcs12 -in file.pfx -nocerts –nodes -passin pass:123 | openssl rsa -out privatekey.pem
This got me a private RSA key, which is then put into FileZilla as the private key and the cert in the cert field in FileZilla's settings. Both of these files should be in a folder not protected by permissions and (not 100% sure on this part) should be in the same folder.

How to create .pfx file from certificate and private key?

I need .pfx file to install https on website on IIS.
I have two separate files: certificate (.cer or pem) and private key (.crt) but IIS accepts only .pfx files.
I obviously installed certificate and it is available in certificate manager (mmc) but when I select Certificate Export Wizard I cannot select PFX format (it's greyed out)
Are there any tools to do that or C# examples of doing that programtically?
You will need to use openssl.
openssl pkcs12 -export -out domain.name.pfx -inkey domain.name.key -in domain.name.crt
The key file is just a text file with your private key in it.
If you have a root CA and intermediate certs, then include them as well using multiple -in params
openssl pkcs12 -export -out domain.name.pfx -inkey domain.name.key -in domain.name.crt -in intermediate.crt -in rootca.crt
If you have a bundled crt file that you use, for example, with nginx, you can pass that in along with the cert all in one:
cat domain.name.crt | tee -a domain.name.bundled.crt
cat intermediate.crt | tee -a domain.name.bundled.crt
cat rootca.crt | tee -a domain.name.bundled.crt
openssl pkcs12 -export -out domain.name.pfx \
-inkey domain.name.key \
-in domain.name.bundled.crt
You can install openssl from here: openssl
If you're looking for a Windows GUI, check out DigiCert. I just used this and it was fairly simple.
Under the SSL tab, I first Imported the Certificate. Then once I selected the Certificate I was able to export as a PFX, both with and without a keyfile.
https://www.digicert.com/util
The Microsoft Pvk2Pfx command line utility seems to have the functionality you need:
Pvk2Pfx (Pvk2Pfx.exe) is a command-line tool copies public key and private key information contained in .spc, .cer, and .pvk files to a Personal Information Exchange (.pfx) file.
http://msdn.microsoft.com/en-us/library/windows/hardware/ff550672(v=vs.85).aspx
Note: if you need/want/prefer a C# solution, then you may want to consider using the http://www.bouncycastle.org/ api.
You do NOT need openssl or makecert or any of that. You also don't need the personal key given to you by your CA. I can almost guarantee that the problem is that you expect to be able to use the key and cer files provided by your CA but they aren't based on "the IIS way".
SSL Certs for IIS with PFX once and for all - SSL and IIS Explained - http://rainabba.blogspot.com/2014/03/ssl-certs-for-iis-with-pfx-once-and-for.html
Use IIS "Server Certificates" UI to "Generate Certificate Request" (the details of this request are out of the scope of this article but those details are critical). This will give you a CSR prepped for IIS. You then give that CSR to your CA and ask for a certificate. Then you take the CER/CRT file they give you, go back to IIS, "Complete Certificate Request" in the same place you generated the request. It may ask for a .CER and you might have a .CRT. They are the same thing. Just change the extension or use the . extension drop-down to select your .CRT. Now provide a proper "friendly name" (*.yourdomain.example, yourdomain.example, foo.yourdomain.example, etc..) THIS IS IMPORTANT! This MUST match what you setup the CSR for and what your CA provided you. If you asked for a wildcard, your CA must have approved and generated a wildcard and you must use the same. If your CSR was generated for foo.yourdomain.example, you MUST provide the same at this step.
Solution for Windows that doesn't require OpenSSL installed
I recently was trying to solve the same issue - and I only had a windows laptop with no openssl installed (and no enough admin rights to install it). Turns out windows has built-in utility called certutil that is capable of combining .crt and .key files into .pfx. Docs are here.
You need to create a new folder and place you .crt and key files in it. Rename both files to have the same name (but different extension):
{{sitename}}.crt
{{siteName}}.key
In case your key file is a regular txt - just change extension to .key.
After that open cmd in that folder and run certutil -mergepfx [INPUTFILE] [OUTPUTFILE]
Example:
certificate file: mySite.crt
key file: mySite.key
certutil command: certutil -mergepfx mySite.crt mySite.pfx
Note: you will be asked to provide password for newly created .pfx file - don't forget to memorise/store it - as it will be required during certificate import on the target system.
I created .pfx file from .key and .pem files.
Like this openssl pkcs12 -inkey rootCA.key -in rootCA.pem -export -out rootCA.pfx
https://msdn.microsoft.com/en-us/library/ff699202.aspx
(( relevant quotes from the article are below ))
Next, you have to create the .pfx file that you will use to sign your deployments. Open a Command Prompt window, and type the following command:
PVK2PFX –pvk yourprivatekeyfile.pvk –spc yourcertfile.cer –pfx yourpfxfile.pfx –po yourpfxpassword
where:
pvk - yourprivatekeyfile.pvk is the private key file that you created in step 4.
spc - yourcertfile.cer is the certificate file you created in step 4.
pfx - yourpfxfile.pfx is the name of the .pfx file that will be creating.
po - yourpfxpassword is the password that you want to assign to the .pfx file. You will be prompted for this password when you add the .pfx file to a project in Visual Studio for the first time.
(Optionally (and not for the OP, but for future readers), you can create the .cer and .pvk file from scratch) (you would do this BEFORE the above). Note the mm/dd/yyyy are placeholders for start and end dates. see msdn article for full documentation.
makecert -sv yourprivatekeyfile.pvk -n "CN=My Certificate Name" yourcertfile.cer -b mm/dd/yyyy -e mm/dd/yyyy -r
From this links:
https://serverfault.com/a/224127/569310
https://stackoverflow.com/a/49784278/7856894
https://stackoverflow.com/a/17284371/7856894
If you need, use this simple command sequence with OpenSSL to generate filessl.key (SSL certificate key file), and filessl.crt (SSL certificate file):
openssl genrsa 2048 > filessl.key
chmod 400 filessl.key
openssl req -new -x509 -nodes -sha256 -days 365 -key filessl.key -out filessl.crt
Until here you must respond to the interactive form (you can find reference info like req.cnf from this other post: https://stackoverflow.com/a/49784278/7856894)
Then, continue with this last command, which will ask you type the Export Password:
openssl pkcs12 -export -out filessl.pfx -inkey filessl.key -in filessl.crt
Ready, it generated your SSL certificate file in .PFX (or .P12) format: filessl.pfx.
This is BY FAR the easiest way to convert *.cer to *.pfx files:
Just download the portable certificate converter from DigiCert:
https://www.digicert.com/util/pfx-certificate-management-utility-import-export-instructions.htm
Execute it, select a file and get your *.pfx!!
You need to use the makecert tool.
Open a command prompt as admin and type the following:
makecert -sky exchange -r -n "CN=<CertificateName>" -pe -a sha1 -len 2048 -ss My "<CertificateName>.cer"
Where <CertifcateName> = the name of your cert to create.
Then you can open the Certificate Manager snap-in for the management console by typing certmgr.msc in the Start menu, click personal > certificates > and your cert should be available.
Here is an article.
https://azure.microsoft.com/documentation/articles/cloud-services-certs-create/
I got a link with your requirement.Combine CRT and KEY Files into a PFX with OpenSSL
Extracts from the above link:
First we need to extract the root CA certificate from the existing
.crt file, because we need this later. So open up the .crt and click
on the Certification Path tab.
Click the topmost certificate (In this case VeriSign) and hit View
Certificate. Select the Details tab and hit Copy to File…
Select Base-64 encoded X.509 (.CER) certificate Save it as rootca.cer
or something similar. Place it in the same folder as the other files.
Rename it from rootca.cer to rootca.crt Now we should have 3 files in
our folder from which we can create a PFX file.
Here is where we need OpenSSL. We can either download and install it
on Windows, or simply open terminal on OSX.
EDIT:
There is a support link with step by step information on how to do install the certificate.
After successfully install, export the certificate, choose .pfx format, include private key.
Important Note: : To export the certificate in .pfx format you need to follow the steps on the same machine from which you have requested the certificate.
The imported file can be uploaded to server.
When you say the certificate is available in MMC, is it available under "Current User" or "Local Computer"? I've found that I can only export the private key if it is under Local Computer.
You can add the snap in for Certificates to MMC and choose which account it should manage certificates for. Choose Local Computer. If your certificate is not there, import it by right clicking the store and choosing All Tasks > Import.
Now navigate to your imported certificate under the Local Computer version of the certificate snap in. Right click the certificate and choose All Tasks > Export. The second page of the export wizard should ask if you want to export the private key. Select Yes. The PFX option will now be the only one available (it is grayed out if you select no and the option to export the private key isn't available under the Current User account).
You'll be asked to set a password for the PFX file and then to set the certificate name.
I was trying openssl on macbook with libreSSL v2.8.3 and was getting error "No certificate matches private key". I had one domain cert, 2 intermediates and 1 root cert. So I used following command which worked successfully:
openssl pkcs12 -export -clcerts -inkey private.csr.key -in domain.name.crt -certfile intermediate1.crt -certfile intermediate2.crt -certfile root.crt -out domain.name.p12 -name "Your Name"
It will ask for a password that will be used during import. This command will generate a .p12 file which can be renamed to .pfx as both are same.
I was having the same issue. My problem was that the computer that generated the initial certificate request had crashed before the extended ssl validation process was completed. I needed to generate a new private key and then import the updated certificate from the certificate provider. If the private key doesn't exist on your computer then you can't export the certificate as pfx. They option is greyed out.
I would like to promote the "X certificate and key manager" or xca.exe, it's like a GUI version of OpenSSL. With that you can generate the pfx file by the following steps:
Import private key in the "Private Keys" tab;
Import the certificate in the "Certificates" tab;
Generate the pfx file by selecting the certificate and then "Export", select PKCS #12 as the format.
That's it.
In most of the cases, if you are unable to export the certificate as a PFX (including the private key) is because MMC/IIS cannot find/don't have access to the private key (used to generate the CSR). These are the steps I followed to fix this issue:
Run MMC as Admin
Generate the CSR using MMC. Follow this instructions to make the certificate exportable.
Once you get the certificate from the CA (crt + p7b), import them (Personal\Certificates, and Intermediate Certification Authority\Certificates)
IMPORTANT: Right-click your new certificate (Personal\Certificates) All Tasks..Manage Private Key, and assign permissions to your account or Everyone (risky!). You can go back to previous permissions once you have finished.
Now, right-click the certificate and select All Tasks..Export, and you should be able to export the certificate including the private key as a PFX file, and you can upload it to Azure!
Hope this helps!
I've written a small console app which converts a PEM certificate file and a private key file to one .pfx PKCS12 certificate file.
It uses BouncyCastle library.
My Github repo: https://github.com/nklkli/PEM-to-PKCS12
Feel free to modify the code to create password protected *.pfx.
openssl pkcs12 -export -in certificate.cer -inkey privateKey.key -out certificate.pfx

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