OpenSSL LoadError 127 in SketchUp 2026

Developers Ruby API
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1

Hello,

I am experiencing a persistent issue with SketchUp Pro 2026 (version 26.0.429) on Windows 11 related to loading OpenSSL within Ruby. The following command, executed in the Ruby Console immediately after a clean installation, consistently fails:

require 'openssl'

The error returned is always:

LoadError: 127 – “The specified procedure could not be found”
File involved:
SketchUp/Tools/RubyStdLib/platform_specific/openssl.so

The same issue also occurs in SketchUp 2025, which indicates that the problem is not limited to version 2026 ?
This error prevents the proper functioning of a professional extension I use: FlexTools.

Technical Findings

• The required files (openssl.so, libcrypto-3-x64.dll, libssl-3-x64.dll) are present in the platform_specific directory.
• Copying these DLLs into the main SketchUp folder has no effect.
• A full clean reinstall (removal of Program Files + AppData + Local folders) produces the same result.
• No antivirus or Windows Security component is blocking the files.
• Microsoft Visual C++ 2015–2022 (x64) Runtime is installed and up to date.
• The issue occurs before installing any extensions, ruling out plugin conflicts.
• The FlexTools developer attempted multiple workarounds; some worked on his system, but none resolve the issue on mine.

My Request

Could you please advise:

  1. Whether this OpenSSL loading problem (openssl.so) with Ruby 3.2.x is a known issue in SketchUp 2025 / 2026,

  2. Whether a fix, an updated openssl.so file, or a Ruby patch is available,

  3. Or if there is an official procedure to repair or restore the OpenSSL libraries bundled with SketchUp.

At this stage, I am unable to use the FlexTools extension on my installation of SketchUp, despite several full clean reinstallations.

Thank you in advance for your assistance. I remain available to provide any additional information or files you may need.

Kind regards,
Thomas Devogèle

2

I am not getting the exception you show in Win 11 for either SU2025 or 2026.
I get a true result when loading OpenSSL into SketchUp Ruby using require.

According to the API Release Notes, SketchUp 2025.0.2 updated OpenSSL to version 3.4.1, however they forgot to update the OpenSSL::VERSION constant. (It still contains the value 3.1.0)

They are not supposed to be located there anyway.

When you installed SketchUp, did you right-click the installer and choose Run as administrator from the context menu. If not, download the offline installer and do it again, using the Repair option. (First reboot your computer to clear out memory and do not run SketchUp before running the installer.)

Also, make sure that these Ruby DLLs have not been copied into the Windows/System32 directory.