Hi there,
we have problems with “Deploy to IIS” and using a selfsigned certificate for ssl-binding on a Server 2019 / IIS-Target (certificate was created within octodeploy).
If we are using a wildcard-cert from a real CA the deployment is working.
We also tried to import the “Octo-Selfsigned-Certificate” to the IIS and tried to bind to ssl manually and got the following errors in IIS:
Internal Error: HRESULT: 0x8007054F
Same Time Event Log / System says:
A fatal error occurred while creating a TLS server credential. The internal error state is 10018.
It seems there is something wrong with the selfsigned certificate created by octodeploy, bot but sure… we hope you can help us 
Please see attached Task-Log (I replaced sensitive data, etc. with XYZ):
Task ID: ServerTasks-204950
Related IDs: Deployments-48284, Channels-1248, Releases-19249, Projects-1208, Spaces-1, Environments-581
Task status: Failed
Task queued: Freitag, 16 April 2021 8:39:27 +02:00
Task started: Freitag, 16 April 2021 8:39:27 +02:00
Task completed: Freitag, 16 April 2021 8:39:48 +02:00
Task duration: 21 seconds
Server version: 2020.5.5+Branch.tags-2020.5.5.Sha.259508a031a95a62ed2dc5c8c41759cdaaa55775
Server node: OCTOPUS02
| == Failed: Deploy XYZ release 1.441-5 to XYZ ==
08:39:27 Verbose | Step 1.2: Deploy to IIS - INT & PROD does not apply to the current environment, and will not be executed
08:39:27 Verbose | Guided failure is not enabled for this task
08:39:48 Fatal | The deployment failed because one or more steps failed. Please see the deployment log for details.
|
| == Success: Acquire packages ==
08:39:27 Info | Acquiring packages
08:39:27 Info | Making a list of packages to acquire
08:39:27 Verbose | Package XYZ v1.44 is required by action ‘Deploy to IIS - DEV & TEST’
08:39:27 Verbose | No packages are required on the Octopus Server
08:39:27 Verbose | Delta compression is enabled for package transfers from the Octopus Server to deployment targets
08:39:27 Verbose | Machine XYZ still needs packages XYZ v1.44 for action (‘Deploy to IIS - DEV & TEST’)
08:39:29 Info | All packages have been acquired
08:39:29 Verbose | Acquire Packages completed
|
| Success: XYZ
|
| Success: Upload package XYZ v1.44
08:39:27 Verbose | Checking package cache for package XYZ v1.44
08:39:27 Info | Package XYZ v1.44 was found in cache. No need to download from feed.
08:39:27 Verbose | Using file: C:\OctopusShare\Packages\Spaces-1\feeds-builtin\XYZ\XYZ.1.44.zip
08:39:27 Verbose | Executable directory is C:\Windows\system32\WindowsPowershell\v1.0
08:39:27 Verbose | Executable name or full path: C:\Windows\system32\WindowsPowershell\v1.0\PowerShell.exe
08:39:27 Verbose | No user context provided. Running as current user.
08:39:27 Verbose | Starting C:\Windows\system32\WindowsPowershell\v1.0\PowerShell.exe in working directory ‘C:\Octopus\Work\20210416063927-204950-633’ using ‘Western European (DOS)’ encoding running as ‘domain\appuser’ with the same environment variables as the launching process
08:39:28 Verbose | Process C:\Windows\system32\WindowsPowershell\v1.0\PowerShell.exe in C:\Octopus\Work\20210416063927-204950-633 exited with code 0
08:39:28 Verbose | Using Calamari.netfx 15.1.6
08:39:28 Verbose | Using Calamari.netfx 15.1.6
08:39:28 Verbose | Executable directory is C:\Windows\system32\WindowsPowershell\v1.0
08:39:28 Verbose | Executable name or full path: C:\Windows\system32\WindowsPowershell\v1.0\PowerShell.exe
08:39:28 Verbose | No user context provided. Running as current user.
08:39:28 Verbose | Starting C:\Windows\system32\WindowsPowershell\v1.0\PowerShell.exe in working directory ‘C:\Octopus\Work\20210416063928-204950-634’ using ‘Western European (DOS)’ encoding running as ‘domain\appuser’ with the same environment variables as the launching process
08:39:28 Info | When a script or process writes to error out on Windows 2019 (1809) with .NET 4.7.2 , PowerShell may terminate it immediately without allowing further code execution. This also causes only part of the error output to be shown… Install .NET 4.8 or later to resolve this problem. More information.
08:39:28 Verbose | Calamari Version: 15.1.6
08:39:28 Verbose | Environment Information:
08:39:28 Verbose | OperatingSystem: Microsoft Windows NT 10.0.17763.0
08:39:28 Verbose | OsBitVersion: x64
08:39:28 Verbose | Is64BitProcess: True
08:39:28 Verbose | CurrentUser: domain\tentacleuser
08:39:28 Verbose | MachineName: XYZ
08:39:28 Verbose | ProcessorCount: 2
08:39:28 Verbose | CurrentDirectory: C:\Octopus\Work\20210416063928-204950-634
08:39:28 Verbose | TempDirectory: C:\Users\XYZ\AppData\Local\Temp\
08:39:28 Verbose | HostProcess: Calamari (2084)
08:39:28 Verbose | Package XYZ 1.44 hash c892ca858136dae1c78fa18da9da2f9c1ba7e790 has already been uploaded
08:39:28 Verbose | Process C:\Windows\system32\WindowsPowershell\v1.0\PowerShell.exe in C:\Octopus\Work\20210416063928-204950-634 exited with code 0
08:39:28 Verbose | Exit code: 0
08:39:28 Info | Package XYZ version 1.44 found in cache. No need to upload this 8.325 MB package. Using C:\Octopus\Files\XYZ@S1.44@F5332D091D9C884589ADCC5847462A07.zip
|
| == Failed: Step 1: Deploy to each environment ==
08:39:48 Fatal | The step failed: Activity Deploy to IIS - DEV & TEST on XYZ failed with error ‘The remote script failed with exit code 1’.
08:39:48 Verbose | Deploy to each environment completed
|
| == Failed: XYZ ==
08:39:29 Verbose | Octopus Server version: 2020.5.5+Branch.tags-2020.5.5.Sha.259508a031a95a62ed2dc5c8c41759cdaaa55775
08:39:29 Verbose | Environment Information:
| IsRunningInContainer: False
| OperatingSystem: Microsoft Windows 10.0.14393
| OsBitVersion: x64
| Is64BitProcess: True
| CurrentUser: domain\tentacleuser
| MachineName: XYZ
| ProcessorCount: 4
| CurrentDirectory: C:\Windows\system32
| TempDirectory: C:\Users\XYZ\AppData\Local\Temp\
| HostProcessName: Octopus.Server
| PID: 3476
08:39:29 Verbose | Executing Deploy to IIS - DEV & TEST (type Deploy to IIS) on XYZ
08:39:29 Verbose | Executable directory is C:\Windows\system32\WindowsPowershell\v1.0
08:39:29 Verbose | Executable name or full path: C:\Windows\system32\WindowsPowershell\v1.0\PowerShell.exe
08:39:29 Verbose | No user context provided. Running as current user.
08:39:29 Verbose | Starting C:\Windows\system32\WindowsPowershell\v1.0\PowerShell.exe in working directory ‘C:\Octopus\Work\20210416063929-204950-635’ using ‘Western European (DOS)’ encoding running as ‘domain\appuser’ with the same environment variables as the launching process
08:39:29 Verbose | Process C:\Windows\system32\WindowsPowershell\v1.0\PowerShell.exe in C:\Octopus\Work\20210416063929-204950-635 exited with code 0
08:39:29 Verbose | Using Calamari.netfx 15.1.6
08:39:29 Verbose | Using Calamari.netfx 15.1.6
08:39:29 Verbose | Executable directory is C:\Windows\system32\WindowsPowershell\v1.0
08:39:29 Verbose | Executable name or full path: C:\Windows\system32\WindowsPowershell\v1.0\PowerShell.exe
08:39:29 Verbose | No user context provided. Running as current user.
08:39:29 Verbose | Starting C:\Windows\system32\WindowsPowershell\v1.0\PowerShell.exe in working directory ‘C:\Octopus\Work\20210416063929-204950-636’ using ‘Western European (DOS)’ encoding running as ‘domain\appuser’ with the same environment variables as the launching process
08:39:30 Info | When a script or process writes to error out on Windows 2019 (1809) with .NET 4.7.2 , PowerShell may terminate it immediately without allowing further code execution. This also causes only part of the error output to be shown… Install .NET 4.8 or later to resolve this problem. More information.
08:39:30 Verbose | Calamari Version: 15.1.6
08:39:30 Verbose | Environment Information:
08:39:30 Verbose | OperatingSystem: Microsoft Windows NT 10.0.17763.0
08:39:30 Verbose | OsBitVersion: x64
08:39:30 Verbose | Is64BitProcess: True
08:39:30 Verbose | CurrentUser: domain\tentacleuser
08:39:30 Verbose | MachineName: XYZ
08:39:30 Verbose | ProcessorCount: 2
08:39:30 Verbose | CurrentDirectory: C:\Octopus\Work\20210416063929-204950-636
08:39:30 Verbose | TempDirectory: C:\Users\XYZ\AppData\Local\Temp\
08:39:30 Verbose | HostProcess: Calamari (2620)
08:39:30 Info | Deploying package: C:\Octopus\Files\XYZ@S1.44@F5332D091D9C884589ADCC5847462A07.zip
08:39:30 Verbose | Extracting package to: C:\Octopus\Applications\XYZ\XYZ\1.44_5
08:39:31 Verbose | Extracted 118 files
08:39:31 Verbose | The file at C:\Octopus\Applications\XYZ\XYZ\1.44_5\appsettings.json matches a known filename pattern, and will be treated as Json.
08:39:31 Verbose | Attempting structured variable replacement on file C:\Octopus\Applications\XYZ\XYZ\1.44_5\appsettings.json with format Json
08:39:31 Verbose | Structure found matching the variable ‘Services:UserManagement:AppKey’. Replacing its content with the variable value.
08:39:31 Verbose | Structure found matching the variable ‘Services:XYZ:Username’. Replacing its content with the variable value.
08:39:31 Verbose | Structure found matching the variable ‘Services:XYZ:Url’. Replacing its content with the variable value.
08:39:31 Verbose | Structure found matching the variable ‘ConnectionStrings:XYZ’. Replacing its content with the variable value.
08:39:31 Verbose | Structure found matching the variable ‘XYZ:Environment’. Replacing its content with the variable value.
08:39:31 Info | Structured variable replacement succeeded on file C:\Octopus\Applications\XYZ\XYZ\1.44_5\appsettings.json with format Json
08:39:31 Verbose | The package has been installed to: C:\Octopus\Applications\XYZ\XYZ\1.44_5
08:39:31 Verbose | If you would like the package to be installed to an alternative location, please use the ‘Custom installation directory’ feature
08:39:31 Verbose | Executing feature-class ‘Calamari.Deployment.Features.IisWebSiteBeforeDeployFeature’
08:39:31 Verbose | Found existing certificate with thumbprint ‘77B50BCD133A1F60DEB1543F64F70186621807CE’ in Cert:\LocalMachine\My
08:39:31 Verbose | Creating ‘C:\Octopus\Applications\XYZ\XYZ\1.44_5\Octopus.Features.IISWebSite_BeforePostDeploy.ps1’ from embedded resource
08:39:31 Verbose | Executing ‘C:\Octopus\Applications\XYZ\XYZ\1.44_5\Octopus.Features.IISWebSite_BeforePostDeploy.ps1’
08:39:31 Verbose | Setting Proxy Environment Variables
08:39:31 Verbose | Name Value
08:39:31 Verbose | ---- -----
08:39:31 Verbose | PSVersion 5.1.17763.592
08:39:31 Verbose | PSEdition Desktop
08:39:31 Verbose | PSCompatibleVersions {1.0, 2.0, 3.0, 4.0…}
08:39:31 Verbose | BuildVersion 10.0.17763.592
08:39:31 Verbose | CLRVersion 4.0.30319.42000
08:39:31 Verbose | WSManStackVersion 3.0
08:39:31 Verbose | PSRemotingProtocolVersion 2.3
08:39:31 Verbose | SerializationVersion 1.1.0.1
08:39:32 Verbose | PowerShell Environment Information:
08:39:32 Verbose | OperatingSystem: Microsoft Windows NT 10.0.17763.0
08:39:32 Verbose | OsBitVersion: x64
08:39:32 Verbose | Is64BitProcess: True
08:39:32 Verbose | CurrentUser: domain\tentacleuser
08:39:32 Verbose | MachineName: XYZ
08:39:32 Verbose | ProcessorCount: 2
08:39:32 Verbose | CurrentDirectory: C:\Octopus\Applications\XYZ\XYZ\1.44_5
08:39:32 Verbose | CurrentLocation: C:\Octopus\Applications\XYZ\XYZ\1.44_5
08:39:32 Verbose | TempDirectory: C:\Users\XYZ\AppData\Local\Temp\
08:39:32 Verbose | HostProcess: powershell (6072)
08:39:32 Verbose | TotalPhysicalMemory: 8387564 KB
08:39:32 Verbose | AvailablePhysicalMemory: 6714812 KB
08:39:32 Verbose | Invoking target script C:\Octopus\Applications\XYZ\XYZ\1.44_5\Octopus.Features.IISWebSite_BeforePostDeploy.ps1 with parameters.
08:39:32 Verbose | Detected IIS Version 10.0
08:39:32 Info | Making sure a Website “XYZ” is configured in IIS…
08:39:32 Info | Finding SSL certificate with thumbprint 77B50BCD133A1F60DEB1543F64F70186621807CE
08:39:32 Info | Found certificate: CN=XYZ in: My
08:39:32 Verbose | Acquired mutex Global\Octopus-IIS-Metabase-Mutex
08:39:33 Info | A different binding exists for the IP/port combination, replacing…
08:39:33 Info | SSL Certificate successfully deleted
08:39:33 Info | SSL Certificate add failed, Error: 1359
08:39:33 Info | An internal error occurred.
08:39:33 Info | Attempt 1 of 5 failed: ScriptHalted
08:39:33 Info | Waiting for 3 seconds before retrying…
08:39:36 Info | Retrying…
08:39:36 Info | Adding a new SSL certificate binding…
08:39:36 Info | SSL Certificate add failed, Error: 1359
08:39:36 Info | An internal error occurred.
08:39:36 Info | Failed adding new SSL binding for certificate with thumbprint ‘77B50BCD133A1F60DEB1543F64F70186621807CE’. Exit code: 1
08:39:36 Info | Attempt 2 of 5 failed: ScriptHalted
08:39:36 Info | Waiting for 3 seconds before retrying…
08:39:39 Info | Retrying…
08:39:39 Info | Adding a new SSL certificate binding…
08:39:40 Info | SSL Certificate add failed, Error: 1359
08:39:40 Info | An internal error occurred.
08:39:40 Info | Failed adding new SSL binding for certificate with thumbprint ‘77B50BCD133A1F60DEB1543F64F70186621807CE’. Exit code: 1
08:39:40 Info | Attempt 3 of 5 failed: ScriptHalted
08:39:40 Info | Waiting for 3 seconds before retrying…
08:39:43 Info | Retrying…
08:39:43 Info | Adding a new SSL certificate binding…
08:39:44 Info | SSL Certificate add failed, Error: 1359
08:39:44 Info | An internal error occurred.
08:39:44 Info | Failed adding new SSL binding for certificate with thumbprint ‘77B50BCD133A1F60DEB1543F64F70186621807CE’. Exit code: 1
08:39:44 Info | Attempt 4 of 5 failed: ScriptHalted
08:39:44 Info | Waiting for 3 seconds before retrying…
08:39:46 Info | Retrying…
08:39:46 Info | Adding a new SSL certificate binding…
08:39:48 Info | SSL Certificate add failed, Error: 1359
08:39:48 Info | An internal error occurred.
08:39:48 Info | Failed adding new SSL binding for certificate with thumbprint ‘77B50BCD133A1F60DEB1543F64F70186621807CE’. Exit code: 1
08:39:48 Error | Calamari.exe : OperationStopped: ScriptHalted
08:39:48 Error | At C:\Octopus\Work\20210416063929-204950-636\Bootstrap.ps1:39 char:1
08:39:48 Error | + & “${env:TentacleHome}\Tools\Calamari.netfx\15.1.6\Calamari.exe” dep …
08:39:48 Error | + ~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~
08:39:48 Error | + CategoryInfo : NotSpecified: (OperationStopped: ScriptHalted:String) [], RemoteException
08:39:48 Error | + FullyQualifiedErrorId : NativeCommandError
08:39:48 Error | At C:\Octopus\Applications\XYZ\XYZ\1.44_5\Octopus.Features.IISWebSite_BeforePostDeploy.ps1:570 char:7
08:39:48 Error | + throw
08:39:48 Error | + ~~~~~
08:39:48 Error | at , C:\Octopus\Applications\XYZ\XYZ\1.44_5\Octopus.Features.IISWebSite_BeforePostDeploy.ps1: line
08:39:48 Error | 570
08:39:48 Error | at Core-Execute-WithRetry,
08:39:48 Error | C:\Octopus\Applications\XYZ\XYZ\1.44_5\Octopus.Features.IISWebSite_BeforePostDeploy.ps1: line 125
08:39:48 Error | at Execute-WithRetry, C:\Octopus\Applications\XYZ\XYZ\1.44_5\Octopus.Features.IISWebSite_BeforePostDeploy.ps1:
08:39:48 Error | line 147
08:39:48 Error | at , C:\Octopus\Applications\XYZ\XYZ\1.44_5\Octopus.Features.IISWebSite_BeforePostDeploy.ps1: line
08:39:48 Error | 511
08:39:48 Error | at , C:\Octopus\Applications\XYZ\XYZ\1.44_5\Octopus.Features.IISWebSite_BeforePostDeploy.ps1: line
08:39:48 Error | 469
08:39:48 Error | at , : line 1
08:39:48 Error | at , C:\Octopus\Applications\XYZ\XYZ\1.44_5\Octopus.FunctionAppenderContext.ps1: line 179
08:39:48 Error | at , C:\Octopus\Applications\XYZ\XYZ\1.44_5\Bootstrap.Octopus.FunctionAppenderContext.ps1: line 1958
08:39:48 Error | at , : line 1
08:39:48 Error | at , : line 1
08:39:48 Verbose | Deleting ‘C:\Octopus\Applications\XYZ\XYZ\1.44_5\Octopus.Features.IISWebSite_BeforePostDeploy.ps1’
08:39:48 Verbose | Calamari.Common.Commands.CommandException: Script ‘C:\Octopus\Applications\XYZ\XYZ\1.44_5\Octopus.Features.IISWebSite_BeforePostDeploy.ps1’ returned non-zero exit code: 1
08:39:48 Verbose | at Calamari.Deployment.Conventions.FeatureConventionBase.ExecuteFeatureScripts(RunningDeployment deployment, String feature, HashSet`1 embeddedResourceNames)
08:39:48 Verbose | at Calamari.Deployment.Conventions.FeatureConventionBase.Run(RunningDeployment deployment)
08:39:48 Verbose | at Calamari.Deployment.ConventionProcessor.RunInstallConventions()
08:39:48 Verbose | at Calamari.Deployment.ConventionProcessor.RunConventions()
08:39:48 Error | Running rollback conventions…
08:39:48 Verbose | Adding journal entry:
08:39:48 Verbose |
08:39:48 Verbose |
08:39:48 Verbose |
08:39:48 Error | Script ‘C:\Octopus\Applications\XYZ\XYZ\1.44_5\Octopus.Features.IISWebSite_BeforePostDeploy.ps1’ returned
08:39:48 Error | non-zero exit code: 1
08:39:48 Verbose | Process C:\Windows\system32\WindowsPowershell\v1.0\PowerShell.exe in C:\Octopus\Work\20210416063929-204950-636 exited with code 1
08:39:48 Verbose | Updating manifest with output variables
08:39:48 Verbose | Updating manifest with action evaluated variables
08:39:48 Fatal | The remote script failed with exit code 1
08:39:48 Fatal | The action Deploy to IIS - DEV & TEST on XYZ failed
