docs: Comment conditions on each test

source/tests/Test-AntiPhishingPolicy.ps1

@@ -12,15 +12,31 @@ function Test-AntiPhishingPolicy {
         # Initialization code, if needed
         #$auditResults = @()
         $recnum = "2.1.7"
+
+        <#
+        Conditions for 2.1.7 (L1) Ensure that an anti-phishing policy has been created
+
+        Validate test for a pass:
+        - Confirm that the automated test results align with the manual audit steps outlined in the CIS benchmark.
+        - Specific conditions to check:
+          - Condition A: Verify that an anti-phishing policy exists in the Microsoft 365 Security Center.
+          - Condition B: Using PowerShell, ensure the anti-phishing policy is configured with appropriate settings such as enabling impersonation protection and spoof intelligence.
+
+        Validate test for a fail:
+        - Confirm that the failure conditions in the automated test are consistent with the manual audit results.
+        - Specific conditions to check:
+          - Condition A: No anti-phishing policy exists in the Microsoft 365 Security Center.
+          - Condition B: Using PowerShell, the anti-phishing policy is not configured with the required settings.
+        #>
     }
 
     process {
 
         try {
-            # 2.1.7 Ensure that an anti-phishing policy has been created
+            # Condition A: Ensure that an anti-phishing policy has been created
-
-            # Retrieve and validate the anti-phishing policies
             $antiPhishPolicies = Get-AntiPhishPolicy
+
+            # Condition B: Verify the anti-phishing policy settings using PowerShell
             $validatedPolicies = $antiPhishPolicies | Where-Object {
                 $_.Enabled -eq $true -and
                 $_.PhishThresholdLevel -ge 2 -and

source/tests/Test-AuditDisabledFalse.ps1

@@ -9,32 +9,48 @@ function Test-AuditDisabledFalse {
     begin {
         # Dot source the class script if necessary
         #. .\source\Classes\CISAuditResult.ps1
+
+        # Conditions for 6.1.1 (L1) Ensure 'AuditDisabled' organizationally is set to 'False'
+        #
+        # Validate test for a pass:
+        # - Confirm that the automated test results align with the manual audit steps outlined in the CIS benchmark.
+        # - Specific conditions to check:
+        #   - Condition A: The `AuditDisabled` organizational setting is set to `False` in the Microsoft 365 admin center.
+        #   - Condition B: Using PowerShell, the `AuditDisabled` property in the organization's configuration is set to `False`.
+        #   - Condition C: Ensure mailbox auditing is enabled by default at the organizational level.
+        #
+        # Validate test for a fail:
+        # - Confirm that the failure conditions in the automated test are consistent with the manual audit results.
+        # - Specific conditions to check:
+        #   - Condition A: The `AuditDisabled` organizational setting is set to `True` in the Microsoft 365 admin center.
+        #   - Condition B: Using PowerShell, the `AuditDisabled` property in the organization's configuration is set to `True`.
+        #   - Condition C: Mailbox auditing is not enabled by default at the organizational level.
+
         # Initialization code, if needed
         $recnum = "6.1.1"
     }
 
     process {
-
         try {
             # 6.1.1 (L1) Ensure 'AuditDisabled' organizationally is set to 'False'
 
-            # Retrieve the AuditDisabled configuration
+            # Retrieve the AuditDisabled configuration (Condition B)
             $auditDisabledConfig = Get-OrganizationConfig | Select-Object AuditDisabled
             $auditNotDisabled = -not $auditDisabledConfig.AuditDisabled
 
             # Prepare failure reasons and details based on compliance
             $failureReasons = if (-not $auditNotDisabled) {
-                "AuditDisabled is set to True"
+                "AuditDisabled is set to True"  # Condition A Fail
             }
             else {
                 "N/A"
             }
 
             $details = if ($auditNotDisabled) {
-                "Audit is not disabled organizationally"
+                "Audit is not disabled organizationally"  # Condition C Pass
             }
             else {
-                "Audit is disabled organizationally"
+                "Audit is disabled organizationally"  # Condition C Fail
             }
 
             # Create and populate the CISAuditResult object

source/tests/Test-AuditLogSearch.ps1

@@ -11,6 +11,24 @@ function Test-AuditLogSearch {
         #. .\source\Classes\CISAuditResult.ps1
         # Initialization code, if needed
         $recnum = "3.1.1"
+
+        <#
+        Conditions for 3.1.1 (L1) Ensure Microsoft 365 audit log search is Enabled
+
+        Validate test for a pass:
+        - Confirm that the automated test results align with the manual audit steps outlined in the CIS benchmark.
+        - Specific conditions to check:
+            - Condition A: Audit log search is enabled in the Microsoft Purview compliance portal.
+            - Condition B: The audit log retains user and admin activity for 90 days.
+            - Condition C: Audit log search capabilities are functional (search results are displayed for activities within the past 30 days).
+
+        Validate test for a fail:
+        - Confirm that the failure conditions in the automated test are consistent with the manual audit results.
+        - Specific conditions to check:
+            - Condition A: Audit log search is not enabled in the Microsoft Purview compliance portal.
+            - Condition B: The audit log does not retain user and admin activity for 90 days.
+            - Condition C: Audit log search capabilities are non-functional (no search results are displayed for activities within the past 30 days).
+        #>
     }
 
     process {
@@ -24,6 +42,7 @@ function Test-AuditLogSearch {
 
             # Prepare failure reasons and details based on compliance
             $failureReasons = if (-not $auditLogResult) {
+                # Condition A (Fail): Audit log search is not enabled in the Microsoft Purview compliance portal
                 "Audit log search is not enabled"
             }
             else {
@@ -31,6 +50,7 @@ function Test-AuditLogSearch {
             }
 
             $details = if ($auditLogResult) {
+                # Condition A (Pass): Audit log search is enabled in the Microsoft Purview compliance portal
                 "UnifiedAuditLogIngestionEnabled: True"
             }
             else {

source/tests/Test-BlockMailForwarding.ps1

@@ -10,6 +10,24 @@ function Test-BlockMailForwarding {
         #. .\source\Classes\CISAuditResult.ps1
         # Initialization code, if needed
         $recnum = "6.2.1"
+
+        <#
+        Conditions for 6.2.1 (L1) Ensure all forms of mail forwarding are blocked and/or disabled
+
+        Validate test for a pass:
+        - Confirm that the automated test results align with the manual audit steps outlined in the CIS benchmark.
+        - Specific conditions to check:
+          - Condition A: Transport rules do not forward email to external domains.
+          - Condition B: Anti-spam outbound policy is configured to disable automatic email forwarding to external domains.
+          - Condition C: No exceptions to the forwarding rules unless explicitly defined by organizational policy.
+
+        Validate test for a fail:
+        - Confirm that the failure conditions in the automated test are consistent with the manual audit results.
+        - Specific conditions to check:
+          - Condition A: One or more transport rules forward email to external domains.
+          - Condition B: Anti-spam outbound policy does not disable automatic email forwarding to external domains.
+          - Condition C: Unapproved exceptions to the forwarding rules are present.
+        #>
     }
 
     process {
@@ -34,6 +52,7 @@ function Test-BlockMailForwarding {
             $details = @()
 
             if ($transportRules.Count -gt 0) {
+                # Fail Condition A
                 $failureReasons += "Mail forwarding rules found: $($transportRules.Name -join ', ')"
                 $details += "Transport Rules Details:`nRule Name|Redirects To"
                 $details += $transportRules | ForEach-Object {
@@ -43,6 +62,7 @@ function Test-BlockMailForwarding {
             }
 
             if ($nonCompliantSpamPoliciesArray.Count -gt 0) {
+                # Fail Condition B
                 $failureReasons += "Outbound spam policies allowing automatic forwarding found."
                 $details += "Outbound Spam Policies Details:`nPolicy|AutoForwardingMode"
                 $details += $nonCompliantSpamPoliciesArray | ForEach-Object {

source/tests/Test-EnableDKIM.ps1

@@ -9,8 +9,25 @@ function Test-EnableDKIM {
     begin {
         # Dot source the class script if necessary
         #. .\source\Classes\CISAuditResult.ps1
+
         # Initialization code, if needed
         $recnum = "2.1.9"
+
+        <#
+        Conditions for 2.1.9 (L1) Ensure DKIM is enabled for all Exchange Online Domains (Automated)
+
+        Validate test for a pass:
+        - Confirm that the automated test results align with the manual audit steps outlined in the CIS benchmark.
+        - Specific conditions to check:
+          - Condition A: DKIM is enabled for all Exchange Online domains in the Microsoft 365 security center.
+          - Condition B: Using the Exchange Online PowerShell Module, the `CnameConfiguration.Enabled` property for each domain is set to `True`.
+
+        Validate test for a fail:
+        - Confirm that the failure conditions in the automated test are consistent with the manual audit results.
+        - Specific conditions to check:
+          - Condition A: DKIM is not enabled for one or more Exchange Online domains in the Microsoft 365 security center.
+          - Condition B: Using the Exchange Online PowerShell Module, the `CnameConfiguration.Enabled` property for one or more domains is set to `False`.
+        #>
     }
 
     process {
@@ -25,17 +42,17 @@ function Test-EnableDKIM {
 
             # Prepare failure reasons and details based on compliance
             $failureReasons = if (-not $dkimResult) {
-            "DKIM is not enabled for some domains"
+                "DKIM is not enabled for some domains"  # Condition A fail
             }
             else {
                 "N/A"
             }
 
             $details = if ($dkimResult) {
-            "All domains have DKIM enabled"
+                "All domains have DKIM enabled"  # Condition A pass
             }
             else {
-            "DKIM not enabled for: $($dkimFailedDomains -join ', ')"
+                "DKIM not enabled for: $($dkimFailedDomains -join ', ')"  # Condition B fail
             }
 
             # Create and populate the CISAuditResult object

source/tests/Test-IdentifyExternalEmail.ps1

@@ -12,6 +12,22 @@ function Test-IdentifyExternalEmail {
 
         # Initialization code, if needed
         $recnum = "6.2.3"
+
+        # Conditions for 6.2.3 (L1) Ensure email from external senders is identified
+        #
+        # Validate test for a pass:
+        # - Confirm that the automated test results align with the manual audit steps outlined in the CIS benchmark.
+        # - Specific conditions to check:
+        #   - Condition A: External tagging is enabled using PowerShell for all identities.
+        #   - Condition B: The BypassAllowList only contains email addresses the organization has permitted to bypass external tagging.
+        #   - Condition C: External sender tag appears in email messages received from external sources.
+        #
+        # Validate test for a fail:
+        # - Confirm that the failure conditions in the automated test are consistent with the manual audit results.
+        # - Specific conditions to check:
+        #   - Condition A: External tagging is not enabled using PowerShell for all identities.
+        #   - Condition B: The BypassAllowList contains unauthorized email addresses.
+        #   - Condition C: External sender tag does not appear in email messages received from external sources.
     }
 
     process {
@@ -25,12 +41,14 @@ function Test-IdentifyExternalEmail {
 
             # Prepare failure reasons and details based on compliance
             $failureReasons = if (-not $externalTaggingEnabled) {
+                # Condition A: External tagging is not enabled using PowerShell for all identities.
                 "External sender tagging is disabled"
             }
             else {
                 "N/A"
             }
 
+            # Details for external tagging configuration
             $details = "Enabled: $($externalTaggingEnabled); AllowList: $($externalInOutlook.AllowList)"
 
             # Create and populate the CISAuditResult object

source/tests/Test-MailTipsEnabled.ps1

@@ -13,6 +13,24 @@ function Test-MailTipsEnabled {
 
         $auditResult = [CISAuditResult]::new()
         $recnum = "6.5.2"
+
+        # Conditions for 6.5.2 (L2) Ensure MailTips are enabled for end users
+        #
+        # Validate test for a pass:
+        # - Confirm that the automated test results align with the manual audit steps outlined in the CIS benchmark.
+        # - Specific conditions to check:
+        #   - Condition A: MailTipsAllTipsEnabled is set to True.
+        #   - Condition B: MailTipsExternalRecipientsTipsEnabled is set to True.
+        #   - Condition C: MailTipsGroupMetricsEnabled is set to True.
+        #   - Condition D: MailTipsLargeAudienceThreshold is set to an acceptable value (default is 25).
+        #
+        # Validate test for a fail:
+        # - Confirm that the failure conditions in the automated test are consistent with the manual audit results.
+        # - Specific conditions to check:
+        #   - Condition A: MailTipsAllTipsEnabled is not set to True.
+        #   - Condition B: MailTipsExternalRecipientsTipsEnabled is not set to True.
+        #   - Condition C: MailTipsGroupMetricsEnabled is not set to True.
+        #   - Condition D: MailTipsLargeAudienceThreshold is not set to an acceptable value (default is 25).
     }
 
     process {
@@ -21,6 +39,8 @@ function Test-MailTipsEnabled {
 
             # Retrieve organization configuration for MailTips settings
             $orgConfig = Get-OrganizationConfig | Select-Object MailTipsAllTipsEnabled, MailTipsExternalRecipientsTipsEnabled, MailTipsGroupMetricsEnabled, MailTipsLargeAudienceThreshold
+
+            # Check the MailTips settings (Conditions A, B, C, D)
             $allTipsEnabled = $orgConfig.MailTipsAllTipsEnabled -and $orgConfig.MailTipsGroupMetricsEnabled -and $orgConfig.MailTipsLargeAudienceThreshold -eq 25
             $externalRecipientsTipsEnabled = $orgConfig.MailTipsExternalRecipientsTipsEnabled
 

source/tests/Test-MailboxAuditingE3.ps1

@@ -6,6 +6,26 @@ function Test-MailboxAuditingE3 {
     )
 
     begin {
+        <#
+        Conditions for 6.1.2 (L1) Ensure mailbox auditing for E3 users is Enabled
+
+        Validate test for a pass:
+        - Confirm that the automated test results align with the manual audit steps outlined in the CIS benchmark.
+        - Specific conditions to check:
+          - Condition A: Mailbox audit logging is enabled for all user mailboxes.
+          - Condition B: The `AuditAdmin` actions include `ApplyRecord`, `Create`, `HardDelete`, `MoveToDeletedItems`, `SendAs`, `SendOnBehalf`, `SoftDelete`, `Update`, `UpdateCalendarDelegation`, `UpdateFolderPermissions`, and `UpdateInboxRules`.
+          - Condition C: The `AuditDelegate` actions include `ApplyRecord`, `Create`, `HardDelete`, `MoveToDeletedItems`, `SendAs`, `SendOnBehalf`, `SoftDelete`, `Update`, `UpdateFolderPermissions`, and `UpdateInboxRules`.
+          - Condition D: The `AuditOwner` actions include `ApplyRecord`, `HardDelete`, `MoveToDeletedItems`, `SoftDelete`, `Update`, `UpdateCalendarDelegation`, `UpdateFolderPermissions`, and `UpdateInboxRules`.
+
+        Validate test for a fail:
+        - Confirm that the failure conditions in the automated test are consistent with the manual audit results.
+        - Specific conditions to check:
+          - Condition A: Mailbox audit logging is not enabled for all user mailboxes.
+          - Condition B: The `AuditAdmin` actions do not include `ApplyRecord`, `Create`, `HardDelete`, `MoveToDeletedItems`, `SendAs`, `SendOnBehalf`, `SoftDelete`, `Update`, `UpdateCalendarDelegation`, `UpdateFolderPermissions`, and `UpdateInboxRules`.
+          - Condition C: The `AuditDelegate` actions do not include `ApplyRecord`, `Create`, `HardDelete`, `MoveToDeletedItems`, `SendAs`, `SendOnBehalf`, `SoftDelete`, `Update`, `UpdateFolderPermissions`, and `UpdateInboxRules`.
+          - Condition D: The `AuditOwner` actions do not include `ApplyRecord`, `HardDelete`, `MoveToDeletedItems`, `SoftDelete`, `Update`, `UpdateCalendarDelegation`, `UpdateFolderPermissions`, and `UpdateInboxRules`.
+        #>
+
         # Dot source the class script if necessary
         #. .\source\Classes\CISAuditResult.ps1
 
@@ -39,12 +59,15 @@ function Test-MailboxAuditingE3 {
                     $missingActions = @()
                     if ($mailbox.AuditEnabled) {
                         foreach ($action in $AdminActions) {
+                            # Condition B: Checking if the `AuditAdmin` actions include required actions
                             if ($mailbox.AuditAdmin -notcontains $action) { $missingActions += "Admin action '$action' missing" }
                         }
                         foreach ($action in $DelegateActions) {
+                            # Condition C: Checking if the `AuditDelegate` actions include required actions
                             if ($mailbox.AuditDelegate -notcontains $action) { $missingActions += "Delegate action '$action' missing" }
                         }
                         foreach ($action in $OwnerActions) {
+                            # Condition D: Checking if the `AuditOwner` actions include required actions
                             if ($mailbox.AuditOwner -notcontains $action) { $missingActions += "Owner action '$action' missing" }
                         }
 
@@ -54,6 +77,7 @@ function Test-MailboxAuditingE3 {
                         }
                     }
                     else {
+                        # Condition A: Checking if mailbox audit logging is enabled
                         $allFailures += "$userUPN|False|||"
                     }
 

source/tests/Test-MailboxAuditingE5.ps1

@@ -9,6 +9,24 @@ function Test-MailboxAuditingE5 {
         # Dot source the class script if necessary
         #. .\source\Classes\CISAuditResult.ps1
 
+        # Conditions for 6.1.3 (L1) Ensure mailbox auditing for E5 users is Enabled
+        #
+        # Validate test for a pass:
+        # - Confirm that the automated test results align with the manual audit steps outlined in the CIS benchmark.
+        # - Specific conditions to check:
+        #   - Condition A: Mailbox auditing is enabled for E5 users.
+        #   - Condition B: AuditAdmin actions include ApplyRecord, Create, HardDelete, MailItemsAccessed, MoveToDeletedItems, Send, SendAs, SendOnBehalf, SoftDelete, Update, UpdateCalendarDelegation, UpdateFolderPermissions, UpdateInboxRules.
+        #   - Condition C: AuditDelegate actions include ApplyRecord, Create, HardDelete, MailItemsAccessed, MoveToDeletedItems, SendAs, SendOnBehalf, SoftDelete, Update, UpdateFolderPermissions, UpdateInboxRules.
+        #   - Condition D: AuditOwner actions include ApplyRecord, HardDelete, MailItemsAccessed, MoveToDeletedItems, Send, SoftDelete, Update, UpdateCalendarDelegation, UpdateFolderPermissions, UpdateInboxRules.
+        #
+        # Validate test for a fail:
+        # - Confirm that the failure conditions in the automated test are consistent with the manual audit results.
+        # - Specific conditions to check:
+        #   - Condition A: Mailbox auditing is not enabled for E5 users.
+        #   - Condition B: AuditAdmin actions do not include all of the following: ApplyRecord, Create, HardDelete, MailItemsAccessed, MoveToDeletedItems, Send, SendAs, SendOnBehalf, SoftDelete, Update, UpdateCalendarDelegation, UpdateFolderPermissions, UpdateInboxRules.
+        #   - Condition C: AuditDelegate actions do not include all of the following: ApplyRecord, Create, HardDelete, MailItemsAccessed, MoveToDeletedItems, SendAs, SendOnBehalf, SoftDelete, Update, UpdateFolderPermissions, UpdateInboxRules.
+        #   - Condition D: AuditOwner actions do not include all of the following: ApplyRecord, HardDelete, MailItemsAccessed, MoveToDeletedItems, Send, SoftDelete, Update, UpdateCalendarDelegation, UpdateFolderPermissions, UpdateInboxRules.
+
         $e5SkuPartNumbers = @("SPE_E5", "ENTERPRISEPREMIUM", "OFFICEE5")
         $AdminActions = @("ApplyRecord", "Copy", "Create", "FolderBind", "HardDelete", "MailItemsAccessed", "Move", "MoveToDeletedItems", "SendAs", "SendOnBehalf", "Send", "SoftDelete", "Update", "UpdateCalendarDelegation", "UpdateFolderPermissions", "UpdateInboxRules")
         $DelegateActions = @("ApplyRecord", "Create", "FolderBind", "HardDelete", "MailItemsAccessed", "Move", "MoveToDeletedItems", "SendAs", "SendOnBehalf", "SoftDelete", "Update", "UpdateFolderPermissions", "UpdateInboxRules")
@@ -38,14 +56,17 @@ function Test-MailboxAuditingE5 {
 
                     $missingActions = @()
                     if ($mailbox.AuditEnabled) {
+                        # Validate Admin actions
                         foreach ($action in $AdminActions) {
-                            if ($mailbox.AuditAdmin -notcontains $action) { $missingActions += "Admin action '$action' missing" }
+                            if ($mailbox.AuditAdmin -notcontains $action) { $missingActions += "Admin action '$action' missing" } # Condition B
                         }
+                        # Validate Delegate actions
                         foreach ($action in $DelegateActions) {
-                            if ($mailbox.AuditDelegate -notcontains $action) { $missingActions += "Delegate action '$action' missing" }
+                            if ($mailbox.AuditDelegate -notcontains $action) { $missingActions += "Delegate action '$action' missing" } # Condition C
                         }
+                        # Validate Owner actions
                         foreach ($action in $OwnerActions) {
-                            if ($mailbox.AuditOwner -notcontains $action) { $missingActions += "Owner action '$action' missing" }
+                            if ($mailbox.AuditOwner -notcontains $action) { $missingActions += "Owner action '$action' missing" } # Condition D
                         }
 
                         if ($missingActions.Count -gt 0) {
@@ -65,10 +86,10 @@ function Test-MailboxAuditingE5 {
             # Prepare failure reasons and details based on compliance
             $failureReasons = if ($allFailures.Count -eq 0) { "N/A" } else { "Audit issues detected." }
             $details = if ($allFailures.Count -eq 0) {
-                "All Office E5 users have correct mailbox audit settings."
+                "All Office E5 users have correct mailbox audit settings." # Condition A for pass
             }
             else {
-                "UserPrincipalName|AuditEnabled|AdminActionsMissing|DelegateActionsMissing|OwnerActionsMissing`n" + ($allFailures -join "`n")
+                "UserPrincipalName|AuditEnabled|AdminActionsMissing|DelegateActionsMissing|OwnerActionsMissing`n" + ($allFailures -join "`n") # Condition A for fail
             }
 
             # Populate the audit result

source/tests/Test-ModernAuthExchangeOnline.ps1

@@ -9,7 +9,23 @@ function Test-ModernAuthExchangeOnline {
     begin {
         # Dot source the class script if necessary
         #. .\source\Classes\CISAuditResult.ps1
-        # Initialization code, if needed
+
+        # Conditions for 6.5.1 (L1) Ensure modern authentication for Exchange Online is enabled
+        #
+        # Validate test for a pass:
+        # - Confirm that the automated test results align with the manual audit steps outlined in the CIS benchmark.
+        # - Specific conditions to check:
+        #   - Condition A: Modern authentication for Exchange Online is enabled.
+        #   - Condition B: Exchange Online clients use modern authentication to log in to Microsoft 365 mailboxes.
+        #   - Condition C: Users of older email clients, such as Outlook 2013 and Outlook 2016, are no longer able to authenticate to Exchange using Basic Authentication.
+        #
+        # Validate test for a fail:
+        # - Confirm that the failure conditions in the automated test are consistent with the manual audit results.
+        # - Specific conditions to check:
+        #   - Condition A: Modern authentication for Exchange Online is not enabled.
+        #   - Condition B: Exchange Online clients do not use modern authentication to log in to Microsoft 365 mailboxes.
+        #   - Condition C: Users of older email clients, such as Outlook 2013 and Outlook 2016, are still able to authenticate to Exchange using Basic Authentication.
+
         $recnum = "6.5.1"
     }
 
@@ -18,6 +34,8 @@ function Test-ModernAuthExchangeOnline {
             # Ensuring the ExchangeOnlineManagement module is available
 
             # 6.5.1 (L1) Ensure modern authentication for Exchange Online is enabled
+
+            # Check modern authentication setting in Exchange Online configuration (Condition A and B)
             $orgConfig = Get-OrganizationConfig | Select-Object -Property Name, OAuth2ClientProfileEnabled
 
             # Prepare failure reasons and details based on compliance
@@ -28,6 +46,7 @@ function Test-ModernAuthExchangeOnline {
                 "N/A"
             }
 
+            # Details include the current setting (Condition A and B)
             $details = "OAuth2ClientProfileEnabled: $($orgConfig.OAuth2ClientProfileEnabled) for Organization: $($orgConfig.Name)"
 
             # Create and populate the CISAuditResult object

source/tests/Test-NoWhitelistDomains.ps1

@@ -9,8 +9,27 @@ function Test-NoWhitelistDomains {
     begin {
         # Dot source the class script if necessary
         #. .\source\Classes\CISAuditResult.ps1
+
         # Initialization code, if needed
         $recnum = "6.2.2"
+
+        <#
+        Conditions for 6.2.2 (L1) Ensure mail transport rules do not whitelist specific domains (Automated)
+
+        Validate test for a pass:
+        - Confirm that the automated test results align with the manual audit steps outlined in the CIS benchmark.
+        - Specific conditions to check:
+          - Condition A: No mail transport rules whitelist any specific domains.
+          - Condition B: Verification of mail transport rules using PowerShell shows no domains are whitelisted.
+          - Condition C: Manual review in Exchange Online admin center confirms no whitelisted domains in transport rules.
+
+        Validate test for a fail:
+        - Confirm that the failure conditions in the automated test are consistent with the manual audit results.
+        - Specific conditions to check:
+          - Condition A: One or more mail transport rules whitelist specific domains.
+          - Condition B: Verification of mail transport rules using PowerShell shows one or more domains are whitelisted.
+          - Condition C: Manual review in Exchange Online admin center shows whitelisted domains in transport rules.
+        #>
     }
 
     process {
@@ -18,9 +37,11 @@ function Test-NoWhitelistDomains {
             # 6.2.2 (L1) Ensure mail transport rules do not whitelist specific domains
 
             # Retrieve transport rules that whitelist specific domains
+            # Condition A: Checking for transport rules that whitelist specific domains
             $whitelistedRules = Get-TransportRule | Where-Object { $_.SetSCL -eq -1 -and $null -ne $_.SenderDomainIs }
 
             # Prepare failure reasons and details based on compliance
+            # Condition B: Prepare failure reasons based on the presence of whitelisted rules
             $failureReasons = if ($whitelistedRules) {
                 "There are transport rules whitelisting specific domains."
             }
@@ -28,6 +49,7 @@ function Test-NoWhitelistDomains {
                 "N/A"
             }
 
+            # Condition C: Prepare details about the whitelisted rules if found
             $details = if ($whitelistedRules) {
                 $ruleDetails = $whitelistedRules | ForEach-Object { "{0}: {1}" -f $_.Name, ($_.SenderDomainIs -join ', ') }
                 "Whitelisted Rules: $($ruleDetails -join '; ')"

source/tests/Test-PasswordHashSync.ps1

@@ -7,6 +7,22 @@ function Test-PasswordHashSync {
     )
 
     begin {
+        # Conditions for 5.1.8.1 (L1) Ensure password hash sync is enabled for hybrid deployments
+        #
+        # Validate test for a pass:
+        # - Confirm that the automated test results align with the manual audit steps outlined in the CIS benchmark.
+        # - Specific conditions to check:
+        #   - Condition A: Password hash sync is enabled in the Azure AD Connect tool on the on-premises server.
+        #   - Condition B: Password hash sync is verified as enabled in the Azure AD Connect Sync section in the Microsoft Entra admin center.
+        #   - Condition C: Using Microsoft Graph PowerShell, the verification command returns the expected result indicating that password sync is enabled for the on-premises AD.
+        #
+        # Validate test for a fail:
+        # - Confirm that the failure conditions in the automated test are consistent with the manual audit results.
+        # - Specific conditions to check:
+        #   - Condition A: Password hash sync is not enabled in the Azure AD Connect tool on the on-premises server.
+        #   - Condition B: Password hash sync is not verified as enabled in the Azure AD Connect Sync section in the Microsoft Entra admin center.
+        #   - Condition C: Using Microsoft Graph PowerShell, the verification command returns no result indicating that password sync is not enabled for the on-premises AD.
+
         # Dot source the class script if necessary
         #. .\source\Classes\CISAuditResult.ps1
         # Initialization code, if needed
@@ -16,9 +32,8 @@ function Test-PasswordHashSync {
     process {
         try {
             # 5.1.8.1 (L1) Ensure password hash sync is enabled for hybrid deployments
-            # Pass if OnPremisesSyncEnabled is True. Fail otherwise.
 
-            # Retrieve password hash sync status
+            # Retrieve password hash sync status (Condition A and C)
             $passwordHashSync = Get-MgOrganization | Select-Object -ExpandProperty OnPremisesSyncEnabled
             $hashSyncResult = $passwordHashSync
 

source/tests/Test-RestrictOutlookAddins.ps1

@@ -9,11 +9,26 @@ function Test-RestrictOutlookAddins {
     begin {
         # Dot source the class script if necessary
         #. .\source\Classes\CISAuditResult.ps1
+
         # Initialization code
         $customPolicyFailures = @()
         $defaultPolicyFailureDetails = @()
         $relevantRoles = @('My Custom Apps', 'My Marketplace Apps', 'My ReadWriteMailbox Apps')
         $recnum = "6.3.1"
+
+        # Conditions for 6.3.1 (L2) Ensure users installing Outlook add-ins is not allowed
+        #
+        # Validate test for a pass:
+        # - Confirm that the automated test results align with the manual audit steps outlined in the CIS benchmark.
+        # - Specific conditions to check:
+        #   - Condition A: Verify that the roles MyCustomApps, MyMarketplaceApps, and MyReadWriteMailboxApps are unchecked under Other roles.
+        #   - Condition B: Using PowerShell, verify that MyCustomApps, MyMarketplaceApps, and MyReadWriteMailboxApps are not assigned to users.
+        #
+        # Validate test for a fail:
+        # - Confirm that the failure conditions in the automated test are consistent with the manual audit results.
+        # - Specific conditions to check:
+        #   - Condition A: One or more of the roles MyCustomApps, MyMarketplaceApps, and MyReadWriteMailboxApps are checked under Other roles.
+        #   - Condition B: Using PowerShell, verify that MyCustomApps, MyMarketplaceApps, and MyReadWriteMailboxApps are assigned to users.
     }
 
     process {
@@ -28,6 +43,8 @@ function Test-RestrictOutlookAddins {
                     if ($policy.RoleAssignmentPolicy) {
                         $rolePolicyDetails = Get-RoleAssignmentPolicy -Identity $policy.RoleAssignmentPolicy
                         $foundRoles = $rolePolicyDetails.AssignedRoles | Where-Object { $_ -in $relevantRoles }
+
+                        # Condition B: Using PowerShell, verify that MyCustomApps, MyMarketplaceApps, and MyReadWriteMailboxApps are not assigned to users.
                         if ($foundRoles) {
                             $customPolicyFailures += "Policy: $($policy.RoleAssignmentPolicy): Roles: $($foundRoles -join ', ')"
                         }
@@ -38,6 +55,8 @@ function Test-RestrictOutlookAddins {
             # Check Default Role Assignment Policy
             $defaultPolicy = Get-RoleAssignmentPolicy "Default Role Assignment Policy"
             $defaultPolicyRoles = $defaultPolicy.AssignedRoles | Where-Object { $_ -in $relevantRoles }
+
+            # Condition A: Verify that the roles MyCustomApps, MyMarketplaceApps, and MyReadWriteMailboxApps are unchecked under Other roles.
             if ($defaultPolicyRoles) {
                 $defaultPolicyFailureDetails = $defaultPolicyRoles
             }

source/tests/Test-RestrictTenantCreation.ps1

@@ -9,8 +9,25 @@ function Test-RestrictTenantCreation {
     begin {
         # Dot source the class script if necessary
         #. .\source\Classes\CISAuditResult.ps1
+
         # Initialization code, if needed
         $recnum = "5.1.2.3"
+
+        <#
+        Conditions for 5.1.2.3 (L1) Ensure 'Restrict non-admin users from creating tenants' is set to 'Yes'
+
+        Validate test for a pass:
+        - Confirm that the automated test results align with the manual audit steps outlined in the CIS benchmark.
+        - Specific conditions to check:
+          - Condition A: Restrict non-admin users from creating tenants is set to 'Yes' in the Azure AD and Entra administration portal.
+          - Condition B: Using PowerShell, the setting for restricting non-admin users from creating tenants is set to 'Yes'.
+
+        Validate test for a fail:
+        - Confirm that the failure conditions in the automated test are consistent with the manual audit results.
+        - Specific conditions to check:
+          - Condition A: Restrict non-admin users from creating tenants is not set to 'Yes' in the Azure AD and Entra administration portal.
+          - Condition B: Using PowerShell, the setting for restricting non-admin users from creating tenants is not set to 'Yes'.
+        #>
     }
 
     process {
@@ -60,5 +77,3 @@ function Test-RestrictTenantCreation {
         return $auditResult
     }
 }
-
-# Additional helper functions (if any)