Intermittent SSL issue trying to load iOS certificates

[OliverBrown-Next]

Description

We have recently started getting SSL errors when trying to install iOS certificates. Our workflow related to this has not changed for a long time. It does work sometimes (with the same certificates) so I don't believe there are any problems with the certificates.

This happens on macOS 15 20241106.316 but we only very recently switched to macOS 15 and it happened on macOS 14 too.

Starting: Install Dist Apple certificate
==============================================================================
Task         : Install Apple certificate
Description  : Install an Apple certificate required to build on a macOS agent machine
Version      : 2.246.5
Author       : Microsoft Corporation
Help         : https://docs.microsoft.com/azure/devops/pipelines/tasks/utility/install-apple-certificate
==============================================================================
/usr/local/bin/openssl pkcs12 -in /Users/runner/work/_temp/EnterpriseDistribution.p12 -nokeys -passin pass:*** | /usr/local/bin/openssl x509 -sha1 -noout -fingerprint -subject -dates -nameopt utf8,sep_semi_plus_space
Error outputting keys and certificates
40CBBC50F87F0000:error:0308010C:digital envelope routines:inner_evp_generic_fetch:unsupported:crypto/evp/evp_fetch.c:355:Global default library context, Algorithm (RC2-40-CBC : 0), Properties ()
Could not find certificate from <stdin>
##[warning]Error parsing certificate. This might be caused by an unsupported algorithm. If you're using old certificate with a new OpenSSL version try to set -legacy flag in opensslPkcsArgs input.
##[error]Error: /usr/local/bin/openssl failed with return code: 1
Finishing: Install Dist Apple certificate

Platforms affected

• Azure DevOps
• GitHub Actions - Standard Runners
• GitHub Actions - Larger Runners

Runner images affected

• Ubuntu 20.04
• Ubuntu 22.04
• Ubuntu 24.04
• macOS 12
• macOS 13
• macOS 13 Arm64
• macOS 14
• macOS 14 Arm64
• macOS 15
• macOS 15 Arm64
• Windows Server 2019
• Windows Server 2022

Image version and build link

Image: macos-15
Version: 20241106.316

Is it regression?

Yes

Expected behavior

Certificate install correctly.

Actual behavior

Certificates not installed.

Repro steps

Attempt to install iOS certificates. I don't know if it something specific to the certificates I'm using though.

[OliverBrown-Next]

I've just discovered this issue, which seems to be the problem and may be a better place:

microsoft/azure-pipelines-tasks#20628

[OliverBrown-Next]

Based on the discussion (and looking at recent runs) I suspect this was intermittent on macOS 14 as the updated agent was rolling out, but is every time on macOS 15.

[susmitamane]

@OliverBrown-Next We will look into the issue and keep you posted with updates.

[thisisthekap]

Seems like macos-15 20241106.316 requires us to add opensslPkcsArgs: -legacy to the InstallAppleCertificate@2 task. But for older image versions (e.g. macos-15 20241022.244) we must not add this line (otherwise the build fails because the legacy argument seems to be unsupported for that case).

The issue that we are currently facing: macOS-15 20241106.316 does not seem to be rolled out to all hosted agents as of now.

[thedee]

I get this same error when doing:
vmImage: 'macos-15'
sudo xcode-select -s /Applications/Xcode_16.app/Contents/Developer

[rkops-bd]

even with opensslPkcsArgs: -legacy this problem happens

[amit-thapa]

Seems like macos-15 20241106.316 requires us to add opensslPkcsArgs: -legacy to the InstallAppleCertificate@2 task. But for older image versions (e.g. macos-15 20241022.244) we must not add this line (otherwise the build fails because the legacy argument seems to be unsupported for that case).

The issue that we are currently facing: macOS-15 20241106.316 does not seem to be rolled out to all hosted agents as of now.

This is what is currently happening to me macos-15 20241106.316 works like a charm and macos-15 20241022.244 doesn't.

[amit-thapa]

even with opensslPkcsArgs: -legacy this problem happens

Depends which version of macos-15 was assigned to the runner

[rkops-bd]

Seems like macos-15 20241106.316 requires us to add opensslPkcsArgs: -legacy to the InstallAppleCertificate@2 task. But for older image versions (e.g. macos-15 20241022.244) we must not add this line (otherwise the build fails because the legacy argument seems to be unsupported for that case).
The issue that we are currently facing: macOS-15 20241106.316 does not seem to be rolled out to all hosted agents as of now.

This is what is currently happening to me macos-15 20241106.316 works like a charm and macos-15 20241022.244 doesn't.

can confirm!

[brentpi]

I converted my key using the following guide; and the issue is resolved:

https://www.docuseal.com/docs/convert-legacy-p12-pfx-files-to-support-openssl-3

Can confirm that legacy, provider legacy, etc did not work prior to having to convert the key.

[amit-thapa]

I converted my key using the following guide; and the issue is resolved:

https://www.docuseal.com/docs/convert-legacy-p12-pfx-files-to-support-openssl-3

Can confirm that legacy, provider legacy, etc did not work prior to having to convert the key.

Hi, what did you use to convert it just regular cmd ?

[sven-s]

I have the same problem also with the image 20241106.316.

/usr/local/bin/openssl pkcs12 -in /Users/runner/work/_temp/Certificate.p12 -nokeys -passin pass:xxxxxx | /usr/local/bin/openssl x509 -sha1 -noout -fingerprint -subject -dates -nameopt utf8,sep_semi_plus_space Error outputting keys and certificates 40FB9549F87F0000:error:0308010C:digital envelope routines:inner_evp_generic_fetch:unsupported:crypto/evp/evp_fetch.c:355:Global default library context, Algorithm (RC2-40-CBC : 0), Properties () Could not find certificate from <stdin> ##[warning]Error parsing certificate. This might be caused by an unsupported algorithm. If you're using old certificate with a new OpenSSL version try to set -legacy flag in opensslPkcsArgs input. ##[error]Error: /usr/local/bin/openssl failed with return code: 1 Finishing: Install cert

Image 20241022.244 runs fine for me, but how to set the image version as a demand?

Edit: I converted the certificate with the link provided and now everything runs fine. @amit-thapa I used just the terminal on my mac, on windows I would try the git bash

Edit again: While the new certificate is running fine with image version 20241106.316, it fails with image version 20241022.244. There is something really rotten.