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Chocolatey and TLS since early 2020

Posted by jpluimers on 2020/03/19

I was upgrading a few older systems that had been off-line for quite a while.

When installing Chocolatey, I bumped into this error:

C:\bin>"%SystemRoot%\System32\WindowsPowerShell\v1.0\powershell.exe" -NoProfile -InputFormat None -ExecutionPolicy Bypass -Command "iex ((New-Object System.Net.WebClient).DownloadString('https://chocolatey.org/install.ps1'))" && SET "PATH=%PATH%;%ALLUSERSPROFILE%\chocolatey\bin"
Exception calling "DownloadString" with "1" argument(s): "The request was aborted: Could not create SSL/TLS secure channel."
At line:1 char:1
+ iex ((New-Object System.Net.WebClient).DownloadString('https://chocol ...
+ ~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~
    + CategoryInfo          : NotSpecified: (:) [], MethodInvocationException
    + FullyQualifiedErrorId : WebException

So I tried [WayBack] chocolatey “The request was aborted: Could not create SSL/TLS secure channel.” – Google Search

Results indicated TLS 1.1 support was removed early February 2020 from Chocolatey because of security reasons, which impacts the installation on older systems:

Note [WayBack] Chocolatey install Error: The request was aborted: Could not create SSL/TLS secure channel – Stack Overflow with a temporary workaround for Microsoft Windows Server 2016:

Looks like the security protocol changed:

Set-ExecutionPolicy Bypass -Scope Process -Force; [System.Net.ServicePointManager]::SecurityProtocol = [System.Net.ServicePointManager]::SecurityProtocol -bor 3072; iex ((New-Object System.Net.WebClient).DownloadString('https://chocolatey.org/install.ps1'))

–jeroen

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