There is a problem when trying to create an TLS/SSL connection on a windows server. I first discussed this on discord mainly with myself :-)

https://discord.com/channels/223421264751099906/223421264751099906/863131080679751680

then sven answered:

This "Error: SSL Exception: connect failed [code:-5]" is new and is not related to Pharo code itself, it happens inside the OS's TLS/SSL code, it is probably related to a change in protocol or certificates. We need to find a way to fix it, but I would not know where to start (I believe it only happens on windows).

My case We want to change our mail sending to smtp.office365.com and TLS (before it was strato without tls) the new service works fine on mac (dev) and on unix (test) but on windows (production) I have a problem, I get "Error: SSL Exception: connect failed [code:-5]"

reproducable with Note that you have to set user and password!

 | theSmtpClient   |
    (theSmtpClient := ZdcSecureSMTPClient new)
        useStartTLS;
        user: 'noreply@xxx.de';
        password: 'xxx'.
    theSmtpClient
        openOnHost: (NetNameResolver addressForName: 'smtp.office365.com' )      
    port: 587

Then the problem exaxtly occurs when calling this primitive:

<primitive: 'primitiveConnect' module: 'SqueakSSL'>

but the SqueakSSL dll is there see below

Version information:

Microsoft Windows Server 2019 Datacenter Version 10

Image

C:\Users\Administrator\Documents\DEV\SPF08071843\Pharo8088.image Pharo8.0.0 Build information: Pharo-8.0.0+build.1141.sha.1b7a8d8203fce2a57794451f555bba4222614081 (64 Bit) Unnamed

Virtual Machine

C:\Users\Administrator\Documents\DEV\Pharo8\Pharo.exe CoInterpreter VMMaker.oscog-eem.2509 uuid: 91e81f64-95de-4914-a960-8f842be3a194 Sep 13 2019 StackToRegisterMappingCogit VMMaker.oscog-eem.2509 uuid: 91e81f64-95de-4914-a960-8f842be3a194 Sep 13 2019 VM: 201907031441-pharo Guille@DESKTOP-MG6660L:projects/vm7/opensmalltalk-vm Date: Wed Jul 3 16:41:39 2019 CommitHash: 4e4c5b5a0 Plugins: 201907031441-pharo Guille@DESKTOP-MG6660L:projects/vm7/opensmalltalk-vm

Win32 built on Sep 13 2019 15:13:35 CEST Compiler: 4.2.1 Compatible Clang 5.0.1 (tags/RELEASE_501/final) VMMaker versionString VM: 201907031441-pharo Guille@DESKTOP-MG6660L:projects/vm7/opensmalltalk-vm Date: Wed Jul 3 16:41:39 2019 CommitHash: 4e4c5b5a0 Plugins: 201907031441-pharo Guille@DESKTOP-MG6660L:projects/vm7/opensmalltalk-vm CoInterpreter VMMaker.oscog-eem.2509 uuid: 91e81f64-95de-4914-a960-8f842be3a194 Sep 13 2019 StackToRegisterMappingCogit VMMaker.oscog-eem.2509 uuid: 91e81f64-95de-4914-a960-8f842be3a194 Sep 13 2019

Virtual Machine Commandline Options

1 C:\Users\Administrator\Documents\DEV\SPF08071843\Pharo8088.image

Loaded VM Modules

B2DPlugin VMMaker.oscog-eem.2480 (i) BitBltPlugin VMMaker.oscog-eem.2493 (i) DSAPrims CryptographyPlugins-eem.14 (i) FileAttributesPlugin FileAttributesPlugin.oscog-akg.49 (e) FilePlugin VMMaker.oscog-eem.2498 (i) FloatArrayPlugin VMMaker.oscog-eem.2480 (i) IA32ABI VMMaker.oscog-eem.2480 (i) JPEGReadWriter2Plugin VMMaker.oscog-eem.2493 (i) Kernel32 LargeIntegers v2.0 VMMaker.oscog-eem.2495 (i) LocalePlugin VMMaker.oscog-eem.2495 (i) Matrix2x3Plugin VMMaker.oscog-eem.2480 (i) MiscPrimitivePlugin VMMaker.oscog-eem.2480 (i) SecurityPlugin VMMaker.oscog-eem.2480 (i) SocketPlugin VMMaker.oscog-eem.2495 (i) SqueakFFIPrims SqueakSSL VMMaker.oscog-eem.2480 (e) SurfacePlugin Sep 13 2019 (e) Win32OSProcessPlugin VMConstruction-Plugins-OSProcessPlugin.oscog-dtl.66 (i) ZipPlugin VMMaker.oscog-eem.2480 (i) kernel32 libfreetype-6.dll libgit2.dll msvcrt.dll

VM Built-in Modules

ADPCMCodecPlugin VMMaker.oscog-eem.2480 (i) AsynchFilePlugin VMMaker.oscog-eem.2493 (i) B2DPlugin VMMaker.oscog-eem.2480 (i) B3DAcceleratorPlugin VMMaker.oscog-eem.2480 (i) BMPReadWriterPlugin VMMaker.oscog-eem.2480 (i) BitBltPlugin VMMaker.oscog-eem.2493 (i) CroquetPlugin VMMaker.oscog-eem.2480 (i) DSAPrims CryptographyPlugins-eem.14 (i) DropPlugin VMMaker.oscog-eem.2480 (i) EventsHandlerPlugin EventsHandlerPlugin-EstebanLorenzano.1 (i) FFTPlugin VMMaker.oscog-eem.2480 (i) FilePlugin VMMaker.oscog-eem.2498 (i) FloatArrayPlugin VMMaker.oscog-eem.2480 (i) FloatMathPlugin VMMaker.oscog-eem.2480 (i) HostWindowPlugin VMMaker.oscog-eem.2493 (i) IA32ABI VMMaker.oscog-eem.2480 (i) JPEGReadWriter2Plugin VMMaker.oscog-eem.2493 (i) JPEGReaderPlugin VMMaker.oscog-eem.2480 (i) JoystickTabletPlugin VMMaker.oscog-eem.2493 (i) LargeIntegers v2.0 VMMaker.oscog-eem.2495 (i) LocalePlugin VMMaker.oscog-eem.2495 (i) MIDIPlugin VMMaker.oscog-eem.2493 (i) Matrix2x3Plugin VMMaker.oscog-eem.2480 (i) MiscPrimitivePlugin VMMaker.oscog-eem.2480 (i) Mpeg3Plugin VMMaker.oscog-eem.2495 (i) RePlugin VMMaker.oscog-eem.2480 (i) SDL2DisplayPlugin SDL2DisplayPlugin-RonieSalgado.1 (i) SecurityPlugin VMMaker.oscog-eem.2480 (i) SerialPlugin VMMaker.oscog-eem.2493 (i) SocketPlugin VMMaker.oscog-eem.2495 (i) SoundCodecPrims VMMaker.oscog-eem.2480 (i) SoundGenerationPlugin VMMaker.oscog-eem.2480 (i) SoundPlugin VMMaker.oscog-eem.2495 (i) SqueakFFIPrims StarSqueakPlugin VMMaker.oscog-eem.2480 (i) UUIDPlugin VMMaker.oscog-eem.2480 (i) Win32OSProcessPlugin VMConstruction-Plugins-OSProcessPlugin.oscog-dtl.66 (i) ZipPlugin VMMaker.oscog-eem.2480 (i)

Operating System Details

Operating System: Windows Server 2019 Datacenter (Build 9200 ) Registered Owner: EC2 Registered Company: Amazon.com SP major version: 0 SP minor version: 0 Suite mask: 190 Product type: 3

pharo-project / pharo

Error: SSL Exception: connect failed [code:-5] TLS/SSL connection on a windows server #9582