Help/Support Sideloadly Failing to Install App on M1 Pro Macbook because of OpenSSL Issue

Skuld9029 · February 8, 2022

Hi all, been trying to resolve this for the better part of today to no avail, so I was wondering if anyone might have seen this or know how to fix this error with Sideloadly on my 2021 M1 Pro Macbook running Monterey 12.1. I jailbroke my iPad mini 2 running on iOS 12.4.7 using checkra1n and used Frida to extract decrypted IPAs.

After adding an IPA to Sideloadly and hit start, I'm able to enter an apple ID and a password, and it is able to obtain my Team ID and detect that my Mac is registered, it fails to actually install because of an error after checking the private key and trying to generate a keypair:

ERROR: Guru Meditation 90837e@94:01234a cffi library '_openssl' has no function, constant or global variable named 'Cryptography_HAS_SIGALGS'

I have tried different Apple ID accounts and different IPAs but I still get the above error.

Any help would be appreciated, thanks!

Rook · February 8, 2022

Hello,

Do you have Python installed on your system?

Does a Sideloadly reinstall help?

Skuld9029 · February 8, 2022

Hi thank you for your reply; I have python 3.9.10 (installed via brew install python) and Python 2.7.18 running on my system. A reinstall of Sideloadly still comes up with the same errors

Rook · February 8, 2022

1 hour ago, Skuld9029 said:

Hi thank you for your reply; I have python 3.9.10 (installed via brew install python) and Python 2.7.18 running on my system. A reinstall of Sideloadly still comes up with the same errors

It's possible that they may be conflicting with Sideloadly.

Are you able to try and temporarily remove or disable them for testing purposes?

Skuld9029 · February 8, 2022

9 minutes ago, Rook said:

It's possible that they may be conflicting with Sideloadly.

Are you able to try and temporarily remove or disable them for testing purposes?

I have uninstalled version 3.9.10 and have found that there is also version 3.8.9. Both this and version 2.7.18 are both in the usr/bin directory, so it seems like this came with the OS. I tried installing the IPA again, but still experiencing the same error

Rook · February 8, 2022

37 minutes ago, Skuld9029 said:

I have uninstalled version 3.9.10 and have found that there is also version 3.8.9. Both this and version 2.7.18 are both in the usr/bin directory, so it seems like this came with the OS. I tried installing the IPA again, but still experiencing the same error

It's possible that those may also be interfering. We'll have to investigate and find a fix for this.

Skuld9029 · February 8, 2022

1 minute ago, Rook said:

It's possible that those may also be interfering. We'll have to investigate and find a fix for this.

I see, is there any information I could provide that would help?

Rook · February 8, 2022

13 minutes ago, Skuld9029 said:

I see, is there any information I could provide that would help?

You can try removing the other Pythons installed for now, but that may be too much of a hassle so probably best you wait for a fix that will hopefully be ready for next update.

Skuld9029 · February 9, 2022

13 hours ago, Rook said:

You can try removing the other Pythons installed for now, but that may be too much of a hassle so probably best you wait for a fix that will hopefully be ready for next update.

I factory reset my Mac since it's pretty new and I didn't have much on it and this seems to have fixed the problem and allowed me to successfully install IPAs via Sideloadly. I think I did some weird things with the Python installs/uninstalls as well as package installations and uninstalls during troubleshooting. Probably uninstalls weren't clean/thorough enough and left conflicting files somewhere.

Rook · February 9, 2022

3 minutes ago, Skuld9029 said:

I factory reset my Mac since it's pretty new and I didn't have much on it and this seems to have fixed the problem and allowed me to successfully install IPAs via Sideloadly. I think I did some weird things with the Python installs/uninstalls as well as package installations and uninstalls during troubleshooting. Probably uninstalls weren't clean/thorough enough and left conflicting files somewhere.

Thank you for your report. We’ll investigate and hopefully fix this issue so it won’t happen again.