Make Octopus Server upgrades download reliably and fail safely

step-templates/tests/upgrade-octopus-server.ScriptBody.Tests.ps1

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+$ErrorActionPreference = "Stop";
+Set-StrictMode -Version "Latest";
+
+$scriptPath = [System.IO.Path]::Combine($PSScriptRoot, "..", "upgrade-octopus-server.ScriptBody.ps1")
+$scriptBody = [System.IO.File]::ReadAllText($scriptPath)
+$scriptBodyWithoutEntryPoint = $scriptBody -replace '(?m)^StartInstallationOfOctopusServer\s*$', ''
+
+# These stubs make the revised internal seams mockable while the tests are red against master.
+function NewOctopusTempFile { [System.IO.Path]::GetTempFileName() }
+function InvokeOctopusDownloadRequest { throw "The ranged downloader is not implemented." }
+
+. ([scriptblock]::Create($scriptBodyWithoutEntryPoint))
+
+function New-FakeDownloadResponse {
+    param(
+        [System.Net.HttpStatusCode] $StatusCode,
+        [long] $ContentLength,
+        [string] $ContentRange,
+        [byte[]] $Content = @()
+    )
+
+    $response = [pscustomobject]@{
+        StatusCode = $StatusCode
+        ContentLength = $ContentLength
+        Headers = @{ "Content-Range" = $ContentRange }
+        Stream = New-Object System.IO.MemoryStream -ArgumentList @(,$Content)
+    }
+    Add-Member -InputObject $response -MemberType ScriptMethod -Name GetResponseStream -Value { $this.Stream }
+    Add-Member -InputObject $response -MemberType ScriptMethod -Name Dispose -Value { $this.Stream.Dispose() }
+    return $response
+}
+
+function msiexec {}
+
+Describe "Upgrade Octopus Server ranged download" {
+    BeforeEach {
+        $script:DownloadedFile = $null
+        $script:Requests = @()
+
+        Mock NewOctopusTempFile {
+            $script:DownloadedFile = [System.IO.Path]::GetTempFileName()
+            return $script:DownloadedFile
+        }
+        Mock New-Object { throw "The legacy WebClient downloader was invoked." } `
+            -ParameterFilter { $TypeName -eq "System.Net.WebClient" }
+        Mock Get-AuthenticodeSignature { [pscustomobject]@{ Status = "Valid" } }
+        Mock Write-Host {}
+        Mock Start-Sleep {}
+    }
+
+    AfterEach {
+        if ($script:DownloadedFile -and (Test-Path -LiteralPath $script:DownloadedFile)) {
+            Remove-Item -LiteralPath $script:DownloadedFile -Force
+        }
+    }
+
+    It "downloads consecutive ranges and returns one validated path" {
+        Mock InvokeOctopusDownloadRequest {
+            $script:Requests += "$Method`:$RangeStart-$RangeEnd"
+            if ($Method -eq "HEAD") {
+                return New-FakeDownloadResponse -StatusCode OK -ContentLength 7
+            }
+
+            $length = [int]($RangeEnd - $RangeStart + 1)
+            return New-FakeDownloadResponse -StatusCode PartialContent `
+                -ContentLength $length `
+                -ContentRange "bytes $RangeStart-$RangeEnd/7" `
+                -Content ([byte[]](1..$length))
+        }
+
+        $result = @(DownloadOctopusServer "2026.3.15954" 3 3)
+
+        $result.Count | Should Be 1
+        $result[0] | Should Be $script:DownloadedFile
+        (Get-Item -LiteralPath $result[0]).Length | Should Be 7
+        $script:Requests -join "," | Should Be "HEAD:-,GET:0-2,GET:3-5,GET:6-6"
+        Assert-MockCalled Get-AuthenticodeSignature -Times 1
+        Assert-MockCalled Write-Host -Times 1 -ParameterFilter { $Object -eq "Download completed" }
+    }
+
+    It "retries a failed range from the last completed byte" {
+        $script:RangeAttempts = 0
+        Mock InvokeOctopusDownloadRequest {
+            if ($Method -eq "HEAD") {
+                return New-FakeDownloadResponse -StatusCode OK -ContentLength 4
+            }
+
+            $script:RangeAttempts++
+            $script:Requests += "$RangeStart-$RangeEnd"
+            if ($script:RangeAttempts -eq 1) { throw "connection reset" }
+            return New-FakeDownloadResponse -StatusCode PartialContent `
+                -ContentLength 4 -ContentRange "bytes 0-3/4" -Content ([byte[]](1, 2, 3, 4))
+        }
+        Mock Write-Warning {}
+
+        $result = DownloadOctopusServer "2026.3.15954" 4 3
+
+        $result | Should Be $script:DownloadedFile
+        $script:Requests -join "," | Should Be "0-3,0-3"
+        Assert-MockCalled Write-Warning -Times 1
+    }
+
+    It "removes the partial file after exhausting the retry limit" {
+        Mock InvokeOctopusDownloadRequest {
+            if ($Method -eq "HEAD") {
+                return New-FakeDownloadResponse -StatusCode OK -ContentLength 4
+            }
+            throw "connection reset"
+        }
+
+        { DownloadOctopusServer "2026.3.15954" 4 3 } | Should Throw "connection reset"
+        Test-Path -LiteralPath $script:DownloadedFile | Should Be $false
+        Assert-MockCalled InvokeOctopusDownloadRequest -Times 3 -ParameterFilter { $Method -eq "GET" }
+    }
+
+    It "rejects an invalid range response and removes the file" {
+        Mock InvokeOctopusDownloadRequest {
+            if ($Method -eq "HEAD") {
+                return New-FakeDownloadResponse -StatusCode OK -ContentLength 3
+            }
+            return New-FakeDownloadResponse -StatusCode OK -ContentLength 3 `
+                -ContentRange $null -Content ([byte[]](1, 2, 3))
+        }
+
+        { DownloadOctopusServer "2026.3.15954" 3 1 } | Should Throw "invalid response"
+        Test-Path -LiteralPath $script:DownloadedFile | Should Be $false
+    }
+
+    It "rejects a range with an unexpected byte count" {
+        Mock InvokeOctopusDownloadRequest {
+            if ($Method -eq "HEAD") {
+                return New-FakeDownloadResponse -StatusCode OK -ContentLength 3
+            }
+            return New-FakeDownloadResponse -StatusCode PartialContent -ContentLength 2 `
+                -ContentRange "bytes 0-2/3" -Content ([byte[]](1, 2))
+        }
+
+        { DownloadOctopusServer "2026.3.15954" 3 1 } | Should Throw "unexpected file length"
+        Test-Path -LiteralPath $script:DownloadedFile | Should Be $false
+    }
+
+    It "rejects an installer without a valid Authenticode signature" {
+        Mock InvokeOctopusDownloadRequest {
+            if ($Method -eq "HEAD") {
+                return New-FakeDownloadResponse -StatusCode OK -ContentLength 3
+            }
+            return New-FakeDownloadResponse -StatusCode PartialContent -ContentLength 3 `
+                -ContentRange "bytes 0-2/3" -Content ([byte[]](1, 2, 3))
+        }
+        Mock Get-AuthenticodeSignature { [pscustomobject]@{ Status = "NotSigned" } }
+
+        { DownloadOctopusServer "2026.3.15954" 3 1 } | Should Throw "Authenticode"
+        Test-Path -LiteralPath $script:DownloadedFile | Should Be $false
+    }
+
+    It "does not stop or install when the download terminates" {
+        Mock DownloadOctopusServer { throw "download failed" }
+        Mock StopOctopusServer {}
+        Mock InstallOctopusServer {}
+        Mock StartOctopusServer {}
+
+        { InstallSetVersionOnOctopusServer "2025.4.10250" "2026.3.15954" } | Should Throw "download failed"
+
+        Assert-MockCalled StopOctopusServer -Times 0
+        Assert-MockCalled InstallOctopusServer -Times 0
+        Assert-MockCalled StartOctopusServer -Times 0
+    }
+}
+
+Describe "Upgrade Octopus Server installation safety" {
+    It "waits for msiexec with one quoted MSI path" {
+        Mock msiexec {}
+        Mock Start-Process { [pscustomobject]@{ ExitCode = 0 } }
+
+        InstallOctopusServer "C:\Temp\Octopus Server.msi"
+
+        Assert-MockCalled msiexec -Times 0
+        Assert-MockCalled Start-Process -Times 1 -ParameterFilter {
+            $expectedArguments = @("/i", '"C:\Temp\Octopus Server.msi"', "/quiet", "/norestart")
+            $argumentDifference = Compare-Object $ArgumentList $expectedArguments -SyncWindow 0
+            ($FilePath -eq "msiexec.exe") -and $Wait -and $PassThru -and ($null -eq $argumentDifference)
+        }
+    }
+
+    It "terminates with the msiexec exit code when installation fails" {
+        Mock msiexec {}
+        Mock Start-Process { [pscustomobject]@{ ExitCode = 1603 } }
+
+        { InstallOctopusServer "C:\Temp\Octopus.msi" } | Should Throw "1603"
+    }
+
+    It "stops, installs, starts, and cleans up in order on success" {
+        $script:Operations = @()
+        Mock DownloadOctopusServer { "C:\Temp\Octopus.msi" }
+        Mock StopOctopusServer { $script:Operations += "stop" }
+        Mock InstallOctopusServer { $script:Operations += "install" }
+        Mock StartOctopusServer { $script:Operations += "start" }
+        Mock RemoveTempFile { $script:Operations += "cleanup" }
+
+        InstallSetVersionOnOctopusServer "2025.4.10250" "2026.3.15954"
+
+        $script:Operations -join "," | Should Be "stop,install,start,cleanup"
+    }
+
+    It "starts the server and cleans up when installation fails" {
+        $script:Operations = @()
+        Mock DownloadOctopusServer { "C:\Temp\Octopus.msi" }
+        Mock StopOctopusServer { $script:Operations += "stop" }
+        Mock InstallOctopusServer { $script:Operations += "install"; throw "installation failed" }
+        Mock StartOctopusServer { $script:Operations += "start" }
+        Mock RemoveTempFile { $script:Operations += "cleanup" }
+
+        { InstallSetVersionOnOctopusServer "2025.4.10250" "2026.3.15954" } | Should Throw "installation failed"
+
+        $script:Operations -join "," | Should Be "stop,install,start,cleanup"
+    }
+
+    It "cleans up without installing or starting when server stop fails" {
+        $script:Operations = @()
+        Mock DownloadOctopusServer { "C:\Temp\Octopus.msi" }
+        Mock StopOctopusServer { $script:Operations += "stop"; throw "stop failed" }
+        Mock InstallOctopusServer { $script:Operations += "install" }
+        Mock StartOctopusServer { $script:Operations += "start" }
+        Mock RemoveTempFile { $script:Operations += "cleanup" }
+
+        { InstallSetVersionOnOctopusServer "2025.4.10250" "2026.3.15954" } | Should Throw "stop failed"
+
+        $script:Operations -join "," | Should Be "stop,cleanup"
+    }
+
+    It "preserves the installation failure and reports a recovery failure" {
+        Mock DownloadOctopusServer { "C:\Temp\Octopus.msi" }
+        Mock StopOctopusServer {}
+        Mock InstallOctopusServer { throw "installation failed" }
+        Mock StartOctopusServer { throw "recovery failed" }
+        Mock RemoveTempFile {}
+        Mock Write-Warning {}
+
+        { InstallSetVersionOnOctopusServer "2025.4.10250" "2026.3.15954" } | Should Throw "installation failed"
+
+        Assert-MockCalled Write-Warning -Times 1 -ParameterFilter { $Message -like "*recovery failed*" }
+        Assert-MockCalled RemoveTempFile -Times 1
+    }
+}
+
+Describe "Upgrade Octopus Server template contract" {
+    BeforeAll {
+        $templatePath = [System.IO.Path]::Combine($PSScriptRoot, "..", "upgrade-octopus-server.json")
+        $template = Get-Content -LiteralPath $templatePath -Raw | ConvertFrom-Json
+    }
+
+    It "preserves the template identity and parameters" {
+        $template.Id | Should Be "4b3a1f09-1827-41bb-88a4-894c6317922b"
+        @($template.Parameters.Name) -join "," | Should Be "InstanceName,InstallPath,SpecificOctopusServerVersionToInstall"
+    }
+
+    It "publishes version 11 with current modification metadata" {
+        $template.Version | Should Be 11
+        $template.'$Meta'.OctopusVersion | Should Be "2026.3.15954"
+        $template.LastModifiedBy | Should Be "bcullman"
+        $template.LastModifiedDate | Should Not BeNullOrEmpty
+    }
+}