diff --git a/.devcontainer.json b/.devcontainer.json
index 396c9ba5de..0c89314809 100644
--- a/.devcontainer.json
+++ b/.devcontainer.json
@@ -11,23 +11,27 @@
             "profile": "default"
         }
     },
-    "extensions": [
-        "DavidAnson.vscode-markdownlint",
-        "eamodio.gitlens",
-        "EditorConfig.EditorConfig",
-        "gruntfuggly.todo-tree",
-        "k--kato.intellij-idea-keybindings",
-        "medo64.render-crlf",
-        "ms-vscode.powershell-preview",
-        "redhat.vscode-yaml",
-        "usernamehw.errorlens",
-        "yzhang.markdown-all-in-one"
-    ],
-    "settings": {
-        "terminal.integrated.defaultProfile.linux": "zsh",
-        "powershell.powerShellDefaultVersion": "PowerShell Core (Linux)",
-        "powershell.powerShellAdditionalExePaths": {
-            "PowerShell Core (Linux)": "/usr/local/bin/pwsh"
+    "customizations": {
+        "vscode": {
+            "extensions": [
+                "DavidAnson.vscode-markdownlint",
+                "eamodio.gitlens",
+                "EditorConfig.EditorConfig",
+                "gruntfuggly.todo-tree",
+                "k--kato.intellij-idea-keybindings",
+                "medo64.render-crlf",
+                "ms-vscode.powershell-preview",
+                "redhat.vscode-yaml",
+                "usernamehw.errorlens",
+                "yzhang.markdown-all-in-one"
+            ],
+            "settings": {
+                "terminal.integrated.defaultProfile.linux": "zsh",
+                "powershell.powerShellDefaultVersion": "PowerShell Core (Linux)",
+                "powershell.powerShellAdditionalExePaths": {
+                    "PowerShell Core (Linux)": "/usr/local/bin/pwsh"
+                }
+            }
         }
     }
 }
diff --git a/CHANGELOG.md b/CHANGELOG.md
index 49d9e0ce9b..63eaa18e7b 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -2,6 +2,7 @@
 
 ## [0.6.5](https://github.com/Ash258/Scoop-Core/milestone/5)
 
+- **Autoupdate**: Properly support multiple items for specific properties
 - **Git**: Call git internally to prevent spawning of `cmd.exe` or `$SHELL`
 - **getopt**: Support multiple same options passed
 - **Config**: Prefer `~/.config/Shovel` over `~/.config/scoop`
@@ -23,7 +24,7 @@
 - **scoop-info**: Adopt new resolve function for parameter passing
 - **Diagnostic**: Ignore completion check when `-noprofile` is used (cmd usage most likely)
 - **commands**: Short option `-a` will not produce default architecture always
-- Increase command startup
+- Improve command startup
 - Prevent MSI installations in NanoServer images
 - Installation will not fail if `commonstartmenu` or `startmenu` system folder is not defined
 - Print not supported message only if operation will be executed
diff --git a/lib/Helpers.ps1 b/lib/Helpers.ps1
index 6205f609fc..7d30d13fd1 100644
--- a/lib/Helpers.ps1
+++ b/lib/Helpers.ps1
@@ -248,7 +248,7 @@ function Invoke-VariableSubstitution {
                     }
                 }
                 'Object[]' {
-                    $newEntity = $newEntity | ForEach-Object { Invoke-VariableSubstitution -Entity $_ -Substitutes $Substitutes -EscapeRegularExpression:$regexEscape }
+                    $newEntity = $newEntity | ForEach-Object { , (Invoke-VariableSubstitution -Entity $_ -Substitutes $Substitutes -EscapeRegularExpression:$regexEscape) }
                 }
                 'PSCustomObject' {
                     $newentity.PSObject.Properties | ForEach-Object { $_.Value = Invoke-VariableSubstitution -Entity $_ -Substitutes $Substitutes -EscapeRegularExpression:$regexEscape }
diff --git a/lib/autoupdate.ps1 b/lib/autoupdate.ps1
index 834ab812fa..a3976346e1 100644
--- a/lib/autoupdate.ps1
+++ b/lib/autoupdate.ps1
@@ -309,46 +309,6 @@ function get_hash_for_app([String] $app, $config, [String] $version, [String] $u
     return $hash
 }
 
-function update_manifest_with_new_version($json, [String] $version, [String] $url, [String] $hash, $architecture = $null) {
-    $json.version = $version
-
-    if ($null -eq $architecture) {
-        if ($json.url -is [System.Array]) {
-            $json.url[0] = $url
-            $json.hash[0] = $hash
-        } else {
-            $json.url = $url
-            $json.hash = $hash
-        }
-    } else {
-        # If there are multiple urls we replace the first one
-        if ($json.architecture.$architecture.url -is [System.Array]) {
-            $json.architecture.$architecture.url[0] = $url
-            $json.architecture.$architecture.hash[0] = $hash
-        } else {
-            $json.architecture.$architecture.url = $url
-            $json.architecture.$architecture.hash = $hash
-        }
-    }
-}
-
-function update_manifest_prop([String] $prop, $json, [Hashtable] $substitutions) {
-    # first try the global property
-    if ($json.$prop -and $json.autoupdate.$prop) {
-        $json.$prop = Invoke-VariableSubstitution -Entity $json.autoupdate.$prop -Substitutes $substitutions
-    }
-
-    # check if there are architecture specific variants
-    if ($json.architecture -and $json.autoupdate.architecture) {
-        $json.architecture | Get-Member -MemberType 'NoteProperty' | ForEach-Object {
-            $architecture = $_.Name
-            if ($json.architecture.$architecture.$prop -and $json.autoupdate.architecture.$architecture.$prop) {
-                $json.architecture.$architecture.$prop = Invoke-VariableSubstitution -Entity (arch_specific $prop $json.autoupdate $architecture) -Substitutes $substitutions
-            }
-        }
-    }
-}
-
 function Get-VersionSubstitution ([String] $Version, [Hashtable] $CustomMatches = @{ }) {
     $firstPart = $Version -split '-' | Select-Object -First 1
     $lastPart = $Version -split '-' | Select-Object -Last 1
@@ -379,76 +339,124 @@ function Get-VersionSubstitution ([String] $Version, [Hashtable] $CustomMatches
     return $versionVariables
 }
 
-function Invoke-Autoupdate ([String] $app, $dir, $json, [String] $version, [Hashtable] $MatchesHashtable, [String] $Extension = '.json', [Switch] $IgnoreArchive) {
-    Write-UserMessage -Message "Autoupdating $app" -Color 'DarkCyan'
-
-    $oldVersion = $json.version
-    $oldJson = $json | ConvertTo-Json -Depth 50 | ConvertFrom-Json # Deep clone object
-    $has_changes = $false
-    $has_errors = $false
-    [bool] $valid = $true
-    $substitutions = Get-VersionSubstitution -Version $version -CustomMatches $MatchesHashtable
+function Update-ManifestProperty {
+    [CmdletBinding()]
+    [OutputType([Boolean])]
+    param (
+        [Parameter(Mandatory)]
+        [Alias('InputObject')]
+        $Manifest,
+        [Parameter(ValueFromPipeline)]
+        [String[]] $Property,
+        [String] $AppName,
+        [String] $Version,
+        [HashTable] $Substitutions
+    )
+
+    begin { $manifestChanged = $false }
+
+    process {
+        $AppName | Out-Null # PowerShell/PSScriptAnalyzer#1472
+
+        foreach ($prop in $Property) {
+            if ($prop -eq 'hash') {
+                if ($Manifest.hash) {
+                    # Substitute new value
+                    $newURL = Invoke-VariableSubstitution -Entity $Manifest.autoupdate.url -Parameters $Substitutions
+                    $newHash = _getHashesForUrls -AppName $AppName -Version $Version -HashExtraction $Manifest.autoupdate.hash -URL $newURL -Substitutions $Substitutions
+
+                    # Update manifest
+                    $Manifest.hash, $propertyChanged = _updateSpecificProperty -Property $Manifest.hash -Value $newHash
+                    $manifestChanged = $manifestChanged -or $propertyChanged
+                } else {
+                    # Arch-spec
+                    $Manifest.architecture | Get-Member -MemberType NoteProperty | ForEach-Object {
+                        $arch = $_.Name
+                        # Substitute new URLS
+                        $newURL = Invoke-VariableSubstitution -Entity (arch_specific 'url' $Manifest.autoupdate $arch) -Parameters $Substitutions
+                        # Calculate/extract hashes
+                        $newHash = _getHashesForUrls -AppName $AppName -Version $Version -HashExtraction (arch_specific 'hash' $Manifest.autoupdate $arch) -URL $newURL -Substitutions $Substitutions
+
+                        # Update manifest
+                        $Manifest.architecture.$arch.hash, $propertyChanged = _updateSpecificProperty -Property $Manifest.architecture.$arch.hash -Value $newHash
+                        $manifestChanged = $manifestChanged -or $propertyChanged
+                    }
+                }
+                # Extract and update hash property
+            } elseif ($Manifest.$prop -and $Manifest.autoupdate.$Prop) {
+                # Substitute new value
+                $autoupdateProperty = $Manifest.autoupdate.$prop
+                $newValue = Invoke-VariableSubstitution -Entity $autoupdateProperty -Substitutes $Substitutions
+
+                if (($autoupdateProperty.GetType().Name -eq 'Object[]') -and ($autoupdateProperty.Length -eq 1)) {
+                    # Make sure it's an array
+                    $newValue = , $newValue
+                }
 
-    if ($json.url) {
-        # Create new url
-        $url = Invoke-VariableSubstitution -Entity $json.autoupdate.url -Substitutes $substitutions
-        $valid = $true
-
-        if ($valid) {
-            # Create hash
-            $hash = get_hash_for_app $app $json.autoupdate.hash $version $url $substitutions
-            if ($null -eq $hash) {
-                $valid = $false
-                Write-UserMessage -Message 'Could not find hash or download URL!' -Color 'DarkRed'
+                # Update manifest
+                $Manifest.$prop, $propertyChanged = _updateSpecificProperty -Property $Manifest.$prop -Value $newValue
+                $manifestChanged = $manifestChanged -or $propertyChanged
+            } elseif ($Manifest.architecture) {
+                # Substitute and update architecture specific property
+                $Manifest.architecture | Get-Member -MemberType NoteProperty | ForEach-Object {
+                    $arch = $_.Name
+                    if ($Manifest.architecture.$arch.$prop -and ($Manifest.autoupdate.architecture.$arch.$prop -or $Manifest.autoupdate.$prop)) {
+                        # Substitute new value
+                        $autoupdateProperty = @(arch_specific $prop $Manifest.autoupdate $arch)
+
+                        $newValue = Invoke-VariableSubstitution -Entity $autoupdateProperty -Substitutes $Substitutions
+                        if (($autoupdateProperty.GetType().Name -eq 'Object[]') -and ($autoupdateProperty.Length -eq 1)) {
+                            # Make sure it's an array
+                            $newValue = , $newValue
+                        }
+
+                        # Update manifest
+                        $Manifest.architecture.$arch.$prop, $propertyChanged = _updateSpecificProperty -Property $Manifest.architecture.$arch.$prop -Value $newValue
+                        $hasManifestChanged = $hasManifestChanged -or $propertyChanged
+                    }
+                }
             }
         }
+    }
 
-        # Write changes to the json object
-        if ($valid) {
-            $has_changes = $true
-            update_manifest_with_new_version $json $version $url $hash
-        } else {
-            $has_errors = $true
-            throw "Could not update $app"
+    end {
+        if (($Version -ne '') -and ($Manifest.version -ne $Version)) {
+            $Manifest.version = $Version
+            $manifestChanged = $true
         }
-    } else {
-        $json.architecture | Get-Member -MemberType 'NoteProperty' | ForEach-Object {
-            $valid = $true
-            $architecture = $_.Name
-
-            # Create new url
-            $url = Invoke-VariableSubstitution -Entity (arch_specific 'url' $json.autoupdate $architecture) -Substitutes $substitutions
-            $valid = $true
-
-            if ($valid) {
-                # Create hash
-                $hash = get_hash_for_app $app (arch_specific 'hash' $json.autoupdate $architecture) $version $url $substitutions
-                if ($null -eq $hash) {
-                    $valid = $false
-                    Write-UserMessage -Message 'Could not find hash or download URL!' -Color 'DarkRed'
-                }
-            }
 
-            # Write changes to the json object
-            if ($valid) {
-                $has_changes = $true
-                update_manifest_with_new_version $json $version $url $hash $architecture
-            } else {
-                $has_errors = $true
-                throw "Could not update $app $architecture"
-            }
+        return $manifestChanged
+    }
+}
+
+function Invoke-Autoupdate ([String] $app, $dir, $json, [String] $version, [Hashtable] $MatchesHashtable, [String] $Extension = '.json', [Switch] $IgnoreArchive) {
+    Write-Host "Autoupdating $app" -ForegroundColor DarkCyan
+
+    # For archive purpose
+    $oldVersion = $json.version
+    $oldJson = $json | ConvertTo-Json -Depth 50 | ConvertFrom-Json # Deep clone object
+
+    $Manifest = $json
+    $substitutions = Get-VersionSubstitution -Version $version -CustomMatches $MatchesHashtable
+
+    # Get properties, which needs to be updated
+    $updatedProperties = @(@($Manifest.autoupdate.PSObject.Properties.Name) -ne 'architecture')
+    if ($Manifest.autoupdate.architecture) {
+        $Manifest.autoupdate.architecture.PSObject.Properties | ForEach-Object {
+            $updatedProperties += $_.Value.PSObject.Properties.Name
         }
     }
 
-    # Update properties
-    update_manifest_prop 'extract_dir' $json $substitutions
-    update_manifest_prop 'changelog' $json $substitutions
+    # Hashes needs to be updated if not explicitly specified
+    if ($updatedProperties -contains 'url') { $updatedProperties += 'hash' }
 
-    # Update license
-    update_manifest_prop 'license' $json $substitutions
+    $updatedProperties = $updatedProperties | Select-Object -Unique
+    debug [$updatedProperties]
+
+    $changed = Update-ManifestProperty -Manifest $Manifest -Property $updatedProperties -AppName $app -Version $version -Substitutions $substitutions
 
     $newManifest = $null
-    if ($has_changes -and !$has_errors) {
+    if ($changed) {
         # Archive older version
         if (!$IgnoreArchive -and ($json.autoupdate.archive -and ($json.autoupdate.archive -eq $true))) {
             $appOldPath = Join-Path $dir "old\$app"
@@ -474,4 +482,110 @@ function Invoke-Autoupdate ([String] $app, $dir, $json, [String] $version, [Hash
     return $newManifest
 }
 
-$__importedAutoupdate__ = $true
+#region Helpers
+function _updateSpecificProperty {
+    <#
+    .SYNOPSIS
+        Helper for updating manifest's property
+    .DESCRIPTION
+        Updates manifest property (String, Array or PSCustomObject).
+    .PARAMETER Property
+        Specifies the name of property to be updated.
+    .PARAMETER Value
+        Specifies the new value of property.
+        Update line by line.
+    .OUTPUTS
+        System.Object[]
+            The first element is new value of property, the second element is change flag
+    #>
+    param (
+        [ValidateNotNull()]
+        [Parameter(Mandatory, ValueFromPipeline)]
+        [Object] $Property,
+        [Parameter(Mandatory)]
+        [Object] $Value
+    )
+    begin {
+        $result = $Property
+        $hasChanged = $false
+    }
+
+    process {
+        # Bind value into property in case the new value is "longer" than current.
+        if (@($Property).Length -lt @($Value).Length) {
+            $result = $Value
+            $hasChanged = $true
+        } else {
+            switch ($Property.GetType().Name) {
+                'String' {
+                    $val = $Value -as [String]
+                    if ($null -ne $val) {
+                        $result = $val
+                        $hasChanged = $true
+                    }
+                }
+                'Object[]' {
+                    $val = @($Value)
+                    for ($i = 0; $i -lt $val.Length; $i++) {
+                        $result[$i], $itemChanged = _updateSpecificProperty -Property $Property[$i] -Value $val[$i]
+                        $hasChanged = $hasChanged -or $itemChanged
+                    }
+                }
+                'PSCustomObject' {
+                    if ($Value -is [PSObject]) {
+                        foreach ($name in $Property.PSObject.Properties.Name) {
+                            if ($Value.$name) {
+                                $result.$name, $itemChanged = _updateSpecificProperty -Property $Property.$name -Value $Value.$name
+                                $hasChanged = $hasChanged -or $itemChanged
+                            }
+                        }
+                    }
+                }
+            }
+        }
+    }
+
+    end { return $result, $hasChanged }
+}
+
+function _getHashesForUrls {
+    <#
+    .SYNOPSIS
+        Helper for extracting hashes.
+    .DESCRIPTION
+        Extract or calculate hash(es) for provided URLs.
+        If number of hash extraction templates is less then URLs, the last template will be reused for the rest URLs.
+    .PARAMETER AppName
+        Specifies the name of the application.
+    .PARAMETER Version
+        Specifies the version of the application.
+    .PARAMETER HashExtraction
+        Specifeis the extraction method.
+    .PARAMETER URL
+        Specifes the links to updated files.
+    .PARAMETER Substitutions
+        Specifes the hashtable with substitutions.
+    #>
+    param (
+        [String] $AppName,
+        [String] $Version,
+        [PSObject[]] $HashExtraction,
+        [String[]] $URL,
+        [HashTable] $Substitutions
+    )
+    $hash = @()
+    for ($i = 0; $i -lt $URL.Length; $i++) {
+        if ($null -eq $HashExtraction) {
+            $extract = $null
+        } else {
+            $extract = $HashExtraction[$i], $HashExtraction[-1] | Select-Object -First 1
+        }
+        $hash += get_hash_for_app $AppName $extract $Version $URL[$i] $Substitutions
+        if ($null -eq $hash[$i]) {
+            throw "Could not update $AppName, hash for $(url_remote_filename $URL[$i]) failed!"
+        }
+    }
+
+    return $hash
+}
+#endregion Helpers
diff --git a/lib/install.ps1 b/lib/install.ps1
index f8c017eeda..1c96840582 100644
--- a/lib/install.ps1
+++ b/lib/install.ps1
@@ -683,7 +683,7 @@ function cookie_header($cookies) {
 }
 
 function is_in_dir($dir, $check) {
-    $check -match "^$([System.Text.RegularExpressions.Regex]::Escape("$dir"))(\\|`$)"
+    return $check -match "^$([System.Text.RegularExpressions.Regex]::Escape("$dir"))([\\/]|`$)"
 }
 
 function ftp_file_size($url) {