#2644 Password protected message compliance (#2645)

* feat: password protected message compliance

* fix: pr reviews

FlowCrypt.xcodeproj/project.pbxproj

@@ -420,9 +420,12 @@
 		D2FD0F692453245E00259FF0 /* Either.swift in Sources */ = {isa = PBXBuildFile; fileRef = D2FD0F682453245E00259FF0 /* Either.swift */; };
 		D2FF6966243115EC007182F0 /* SetupImapViewController.swift in Sources */ = {isa = PBXBuildFile; fileRef = D2FF6965243115EC007182F0 /* SetupImapViewController.swift */; };
 		D2FF6968243115F9007182F0 /* SetupImapViewDecorator.swift in Sources */ = {isa = PBXBuildFile; fileRef = D2FF6967243115F9007182F0 /* SetupImapViewDecorator.swift */; };
+		D717EC262D06B37E00AE7BFF /* CustomAlertNode.swift in Sources */ = {isa = PBXBuildFile; fileRef = D717EC252D06B37900AE7BFF /* CustomAlertNode.swift */; };
 		D73F7D9D2CD46AE900955806 /* PgpOnlySwitchNode.swift in Sources */ = {isa = PBXBuildFile; fileRef = D73F7D9C2CD46AE700955806 /* PgpOnlySwitchNode.swift */; };
 		D73F7D9F2CD4922500955806 /* NotificationExtension.swift in Sources */ = {isa = PBXBuildFile; fileRef = D73F7D9E2CD4922100955806 /* NotificationExtension.swift */; };
 		D741F9B22CA5661C00E1CAFF /* SecurityWarningNode.swift in Sources */ = {isa = PBXBuildFile; fileRef = D741F9B12CA5661400E1CAFF /* SecurityWarningNode.swift */; };
+		D7478BDE2D09113100D42659 /* PasswordProtectedMsgTest.swift in Sources */ = {isa = PBXBuildFile; fileRef = D7478BDD2D09112500D42659 /* PasswordProtectedMsgTest.swift */; };
+		D7478BE02D0912E600D42659 /* CoreAlertNode.swift in Sources */ = {isa = PBXBuildFile; fileRef = D7478BDF2D0912E200D42659 /* CoreAlertNode.swift */; };
 		F191F621272511790053833E /* BlurViewController.swift in Sources */ = {isa = PBXBuildFile; fileRef = F191F620272511790053833E /* BlurViewController.swift */; };
 		F8678DCC2722143300BB1710 /* GmailService+draft.swift in Sources */ = {isa = PBXBuildFile; fileRef = F8678DCB2722143300BB1710 /* GmailService+draft.swift */; };
 		F8A72FA12729F82800E4BCAB /* DraftGatewayMock.swift in Sources */ = {isa = PBXBuildFile; fileRef = F8A72FA02729F82800E4BCAB /* DraftGatewayMock.swift */; };
@@ -889,9 +892,12 @@
 		D2FD0F682453245E00259FF0 /* Either.swift */ = {isa = PBXFileReference; lastKnownFileType = sourcecode.swift; path = Either.swift; sourceTree = "<group>"; };
 		D2FF6965243115EC007182F0 /* SetupImapViewController.swift */ = {isa = PBXFileReference; lastKnownFileType = sourcecode.swift; path = SetupImapViewController.swift; sourceTree = "<group>"; };
 		D2FF6967243115F9007182F0 /* SetupImapViewDecorator.swift */ = {isa = PBXFileReference; lastKnownFileType = sourcecode.swift; path = SetupImapViewDecorator.swift; sourceTree = "<group>"; };
+		D717EC252D06B37900AE7BFF /* CustomAlertNode.swift */ = {isa = PBXFileReference; lastKnownFileType = sourcecode.swift; path = CustomAlertNode.swift; sourceTree = "<group>"; };
 		D73F7D9C2CD46AE700955806 /* PgpOnlySwitchNode.swift */ = {isa = PBXFileReference; lastKnownFileType = sourcecode.swift; path = PgpOnlySwitchNode.swift; sourceTree = "<group>"; };
 		D73F7D9E2CD4922100955806 /* NotificationExtension.swift */ = {isa = PBXFileReference; lastKnownFileType = sourcecode.swift; path = NotificationExtension.swift; sourceTree = "<group>"; };
 		D741F9B12CA5661400E1CAFF /* SecurityWarningNode.swift */ = {isa = PBXFileReference; lastKnownFileType = sourcecode.swift; path = SecurityWarningNode.swift; sourceTree = "<group>"; };
+		D7478BDD2D09112500D42659 /* PasswordProtectedMsgTest.swift */ = {isa = PBXFileReference; lastKnownFileType = sourcecode.swift; path = PasswordProtectedMsgTest.swift; sourceTree = "<group>"; };
+		D7478BDF2D0912E200D42659 /* CoreAlertNode.swift */ = {isa = PBXFileReference; lastKnownFileType = sourcecode.swift; path = CoreAlertNode.swift; sourceTree = "<group>"; };
 		E26D5E20275AA417007B8802 /* BundleExtensions.swift */ = {isa = PBXFileReference; lastKnownFileType = sourcecode.swift; path = BundleExtensions.swift; sourceTree = "<group>"; };
 		F191F620272511790053833E /* BlurViewController.swift */ = {isa = PBXFileReference; lastKnownFileType = sourcecode.swift; path = BlurViewController.swift; sourceTree = "<group>"; };
 		F8678DCB2722143300BB1710 /* GmailService+draft.swift */ = {isa = PBXFileReference; lastKnownFileType = sourcecode.swift; path = "GmailService+draft.swift"; sourceTree = "<group>"; };
@@ -1502,6 +1508,7 @@
 		9F4164162665757700106194 /* PGP */ = {
 			isa = PBXGroup;
 			children = (
+				D7478BDD2D09112500D42659 /* PasswordProtectedMsgTest.swift */,
 				9FA0157926565B7800CBBA05 /* KeyMethodsTest.swift */,
 			);
 			path = PGP;
@@ -2261,6 +2268,7 @@
 		D2A1D3D223FD9AE600D626D6 /* Nodes */ = {
 			isa = PBXGroup;
 			children = (
+				D7478BDF2D0912E200D42659 /* CoreAlertNode.swift */,
 				D73F7D9C2CD46AE700955806 /* PgpOnlySwitchNode.swift */,
 				9F7ECCA6272C3FB4008A1770 /* TextImageNode.swift */,
 				51EBC56F2746A06600178DE8 /* TextWithIconNode.swift */,
@@ -2282,6 +2290,7 @@
 				51DAD9BC273E7DD20076CBA7 /* BadgeNode.swift */,
 				51B9EE6E27567B520080B2D5 /* MessageRecipientsNode.swift */,
 				9547EF202A5F106E00A048FF /* PassPhraseAlertNode.swift */,
+				D717EC252D06B37900AE7BFF /* CustomAlertNode.swift */,
 				95E014CE2A8BF27C00D4B4F5 /* AvatarCheckboxNode.swift */,
 				9577CEDC2AA7A4A40084AC62 /* PublicKeyDetailNode.swift */,
 				955475FA2B0650AC00F52076 /* WebNode.swift */,
@@ -2618,6 +2627,7 @@
 				9F5F504A26FA6C8F00294FA2 /* ClientConfigurationProviderMock.swift in Sources */,
 				9FC4117D268118AE004C0A69 /* PassPhraseStorageMock.swift in Sources */,
 				9F97650E267E16620058419D /* WKDURLsConstructorTests.swift in Sources */,
+				D7478BDE2D09113100D42659 /* PasswordProtectedMsgTest.swift in Sources */,
 				9F976585267E194F0058419D /* FlowCryptCoreTests.swift in Sources */,
 				9F6F3C3C26ADFBC7005BD9C6 /* CoreComposeMessageMock.swift in Sources */,
 				9FC4116B2681186D004C0A69 /* KeyMethodsTest.swift in Sources */,
@@ -2899,11 +2909,13 @@
 				D211CE7123FC35AC00D1CE38 /* TextFieldCellNode.swift in Sources */,
 				D73F7D9D2CD46AE900955806 /* PgpOnlySwitchNode.swift in Sources */,
 				9FA19890253C841F008C9CF2 /* TableViewController.swift in Sources */,
+				D717EC262D06B37E00AE7BFF /* CustomAlertNode.swift in Sources */,
 				51DAD9BD273E7DD20076CBA7 /* BadgeNode.swift in Sources */,
 				51DE2FEE2714DA0400916222 /* ContactKeyCellNode.swift in Sources */,
 				9547EF242A5FBA2B00A048FF /* MenuSeparatorCellNode.swift in Sources */,
 				D2A9CA432426210200E1D898 /* SetupTitleNode.swift in Sources */,
 				D2F6D12F24324ACC00DB4065 /* SwitchCellNode.swift in Sources */,
+				D7478BE02D0912E600D42659 /* CoreAlertNode.swift in Sources */,
 				51EBC5702746A06600178DE8 /* TextWithIconNode.swift in Sources */,
 				5180CB97273724E9001FC7EF /* ThreadMessageInfoCellNode.swift in Sources */,
 				D2E26F6824F169E300612AF1 /* ContactCellNode.swift in Sources */,

FlowCrypt/Controllers/Compose/ComposeViewController.swift

@@ -56,7 +56,7 @@ final class ComposeViewController: TableNodeViewController {
     let photosManager: PhotosManagerType
     let router: GlobalRouterType
 
-    private let clientConfiguration: ClientConfiguration
+    let clientConfiguration: ClientConfiguration
     var isMessagePasswordSupported: Bool { clientConfiguration.isUsingFes }
 
     let search = PassthroughSubject<String, Never>()

FlowCrypt/Controllers/Compose/Extensions/ComposeViewController+Drafts.swift

@@ -71,6 +71,7 @@ extension ComposeViewController {
                     contextToSend.hasRecipientsWithActivePubKey
 
                 let sendableMsg = try await composeMessageHelper.createSendableMsg(
+                    clientConfiguration: clientConfiguration,
                     input: draft.input,
                     contextToSend: draft.contextToSend,
                     shouldValidate: false,

FlowCrypt/Controllers/Compose/Extensions/ComposeViewController+ErrorHandling.swift

@@ -79,6 +79,8 @@ extension ComposeViewController {
             } else {
                 refreshEKMAndProceed(error: error)
             }
+        case let MessageValidationError.messagePasswordDisallowed(error):
+            alertsFactory.makeCustomAlert(viewController: self, message: error)
         case MessageValidationError.notUniquePassword,
              MessageValidationError.subjectContainsPassword,
              MessageValidationError.weakPassword:

FlowCrypt/Controllers/Compose/Extensions/ComposeViewController+MessageSend.swift

@@ -55,8 +55,10 @@ extension ComposeViewController {
 
     private func sendMessage(isPlain: Bool) async throws -> MessageIdentifier {
         let sendableMsg = try await composeMessageHelper.createSendableMsg(
+            clientConfiguration: clientConfiguration,
             input: input,
             contextToSend: contextToSend,
+            shouldSendPlainMessage: isPlain,
             shouldSign: !isPlain,
             withPubKeys: !isPlain
         )

FlowCrypt/Controllers/Threads/Models/AlertsFactory.swift

@@ -79,6 +79,25 @@ class AlertsFactory {
 
         viewController.present(alertViewController, animated: true, completion: nil)
     }
+
+    func makeCustomAlert(
+        viewController: UIViewController,
+        title: String = "error".localized,
+        message: String
+    ) {
+        let alertNode = CustomAlertNode(
+            title: title,
+            message: message
+        )
+        alertNode.onOkay = {
+            viewController.dismiss(animated: true)
+        }
+        let alertViewController = ASDKViewController(node: alertNode)
+        alertViewController.modalPresentationStyle = UIModalPresentationStyle.overCurrentContext
+        alertViewController.modalTransitionStyle = UIModalTransitionStyle.crossDissolve
+
+        viewController.present(alertViewController, animated: true, completion: nil)
+    }
 }
 
 class SubmitOnPasteTextFieldDelegate: NSObject, UITextFieldDelegate {

FlowCrypt/Functionality/DataManager/Encrypted Storage/EncryptedStorage.swift

@@ -53,6 +53,7 @@ final class EncryptedStorage: EncryptedStorageType {
         case version15
         case version16
         case version17
+        case version18
 
         var version: SchemaVersion {
             switch self {
@@ -84,14 +85,16 @@ final class EncryptedStorage: EncryptedStorageType {
                 return SchemaVersion(appVersion: "1.2.3", dbSchemaVersion: 16)
             case .version17:
                 return SchemaVersion(appVersion: "1.3.0", dbSchemaVersion: 17)
+            case .version18:
+                return SchemaVersion(appVersion: "1.3.0", dbSchemaVersion: 18)
             }
         }
     }
 
     private lazy var migrationLogger = Logger.nested(in: Self.self, with: .migration)
     private lazy var logger = Logger.nested(Self.self)
 
-    private let currentSchema: EncryptedStorageSchema = .version17
+    private let currentSchema: EncryptedStorageSchema = .version18
     private let supportedSchemas = EncryptedStorageSchema.allCases
 
     private let storageEncryptionKey: Data

FlowCrypt/Functionality/Services/Client Configuration Provider/ClientConfiguration.swift

@@ -64,6 +64,16 @@ class ClientConfiguration {
         raw.enforceKeygenAlgo
     }
 
+    /// An array of strings to check against the subject of the composed password-protected message. If any string in this array is found in the subject, an error alert must be displayed
+    var disallowPasswordMessagesForTerms: [String]? {
+        raw.disallowPasswordMessagesForTerms
+    }
+
+    /// The text to be displayed in the password protected message compliance error alert.
+    var disallowPasswordMessagesErrorText: String? {
+        raw.disallowPasswordMessagesErrorText
+    }
+
     /// Some orgs want to have newly generated keys include self-signatures that expire some time in the future.
     var getEnforcedKeygenExpirationMonths: Int? {
         raw.enforceKeygenExpireMonths

FlowCrypt/Functionality/Services/Compose Message Helper/ComposeMessageError.swift

@@ -21,6 +21,7 @@ enum MessageValidationError: Error, CustomStringConvertible, Equatable {
     case expiredKeyRecipients
     case notUsableForEncryptionKeyRecipients
     case invalidEmailRecipient
+    case messagePasswordDisallowed(String)
     case internalError(String)
 
     var description: String {
@@ -49,6 +50,8 @@ enum MessageValidationError: Error, CustomStringConvertible, Equatable {
             return "compose_recipient_unusuable_for_encryption".localized
         case .invalidEmailRecipient:
             return "compose_recipient_invalid_email".localized
+        case let .messagePasswordDisallowed(message):
+            return message
         case let .internalError(message):
             return message
         }

FlowCrypt/Functionality/Services/Compose Message Helper/ComposeMessageHelper.swift

@@ -99,8 +99,10 @@ final class ComposeMessageHelper {
     // MARK: - Validation
     // swiftlint:disable:next function_body_length
     func createSendableMsg(
+        clientConfiguration: ClientConfiguration,
         input: ComposeMessageInput,
         contextToSend: ComposeMessageContext,
+        shouldSendPlainMessage: Bool = true,
         shouldValidate: Bool = true,
         shouldSign: Bool = true,
         withPubKeys: Bool = true
@@ -136,6 +138,14 @@ final class ComposeMessageHelper {
                 throw MessageValidationError.emptyMessage
             }
 
+            if !shouldSendPlainMessage,
+               contextToSend.hasRecipientsWithoutPubKey,
+               let termsToDisallow = clientConfiguration.disallowPasswordMessagesForTerms,
+               let errorText = clientConfiguration.disallowPasswordMessagesErrorText,
+               !subject.isPasswordMessageEnabled(disallowTerms: termsToDisallow) {
+                throw MessageValidationError.messagePasswordDisallowed(errorText)
+            }
+
             if let password = contextToSend.messagePassword, password.isNotEmpty {
                 if subject.lowercased().contains(password.lowercased()) {
                     throw MessageValidationError.subjectContainsPassword

FlowCrypt/Models/Common/RawClientConfiguration.swift

@@ -40,6 +40,8 @@ struct RawClientConfiguration: Codable, Equatable {
     let disallowAttesterSearchForDomains: [String]?
     let enforceKeygenAlgo: String?
     let enforceKeygenExpireMonths: Int?
+    let disallowPasswordMessagesForTerms: [String]?
+    let disallowPasswordMessagesErrorText: String?
 
     init(
         flags: [ClientConfigurationFlag]? = nil,
@@ -50,7 +52,9 @@ struct RawClientConfiguration: Codable, Equatable {
         allowAttesterSearchOnlyForDomains: [String]? = nil,
         disallowAttesterSearchForDomains: [String]? = nil,
         enforceKeygenAlgo: String? = nil,
-        enforceKeygenExpireMonths: Int? = nil
+        enforceKeygenExpireMonths: Int? = nil,
+        disallowPasswordMessagesForTerms: [String]? = nil,
+        disallowPasswordMessagesErrorText: String? = nil
     ) {
         self.flags = flags
         self.customKeyserverUrl = customKeyserverUrl
@@ -61,6 +65,8 @@ struct RawClientConfiguration: Codable, Equatable {
         self.disallowAttesterSearchForDomains = disallowAttesterSearchForDomains
         self.enforceKeygenAlgo = enforceKeygenAlgo
         self.enforceKeygenExpireMonths = enforceKeygenExpireMonths
+        self.disallowPasswordMessagesForTerms = disallowPasswordMessagesForTerms
+        self.disallowPasswordMessagesErrorText = disallowPasswordMessagesErrorText
     }
 }
 
@@ -96,7 +102,11 @@ extension RawClientConfiguration {
                 try JSONDecoder().decode([String].self, from: $0)
             },
             enforceKeygenAlgo: unwrappedObject.enforceKeygenAlgo,
-            enforceKeygenExpireMonths: unwrappedObject.enforceKeygenExpireMonths
+            enforceKeygenExpireMonths: unwrappedObject.enforceKeygenExpireMonths,
+            disallowPasswordMessagesForTerms: try? object?.disallowPasswordMessagesForTerms.ifNotNil {
+                try JSONDecoder().decode([String].self, from: $0)
+            },
+            disallowPasswordMessagesErrorText: unwrappedObject.disallowPasswordMessagesErrorText
         )
     }
 }

FlowCrypt/Models/Realm Models/ClientConfigurationRealmObject.swift

@@ -19,6 +19,8 @@ final class ClientConfigurationRealmObject: Object {
     @Persisted var disallowAttesterSearchForDomains: Data?
     @Persisted var enforceKeygenAlgo: String?
     @Persisted var enforceKeygenExpireMonths: Int
+    @Persisted var disallowPasswordMessagesForTerms: Data?
+    @Persisted var disallowPasswordMessagesErrorText: String?
 
     convenience init(
         flags: [String]?,
@@ -30,6 +32,8 @@ final class ClientConfigurationRealmObject: Object {
         disallowAttesterSearchForDomains: [String]?,
         enforceKeygenAlgo: String?,
         enforceKeygenExpireMonths: Int?,
+        disallowPasswordMessagesForTerms: [String]?,
+        disallowPasswordMessagesErrorText: String?,
         email: String
     ) {
         self.init()
@@ -44,6 +48,8 @@ final class ClientConfigurationRealmObject: Object {
         self.disallowAttesterSearchForDomains = try? disallowAttesterSearchForDomains.ifNotNil { try JSONEncoder().encode($0) }
         self.enforceKeygenAlgo = enforceKeygenAlgo
         self.enforceKeygenExpireMonths = enforceKeygenExpireMonths ?? -1
+        self.disallowPasswordMessagesForTerms = try? disallowPasswordMessagesForTerms.ifNotNil { try JSONEncoder().encode($0) }
+        self.disallowPasswordMessagesErrorText = disallowPasswordMessagesErrorText
         self.userEmail = email
     }
 }
@@ -60,6 +66,8 @@ extension ClientConfigurationRealmObject {
             disallowAttesterSearchForDomains: configuration.disallowAttesterSearchForDomains,
             enforceKeygenAlgo: configuration.enforceKeygenAlgo,
             enforceKeygenExpireMonths: configuration.enforceKeygenExpireMonths,
+            disallowPasswordMessagesForTerms: configuration.disallowPasswordMessagesForTerms,
+            disallowPasswordMessagesErrorText: configuration.disallowPasswordMessagesErrorText,
             email: email
         )
     }

FlowCryptAppTests/Functionality/PGP/PasswordProtectedMsgTest.swift

@@ -0,0 +1,33 @@
+//
+//  PasswordProtectedMsgTest.swift
+//  FlowCryptTests
+//
+//  Created by Ioan Moldovan on 20.05.2021.
+//  Copyright © 2017-present FlowCrypt a. s. All rights reserved.
+//
+
+@testable import FlowCrypt
+import XCTest
+
+class PasswordProtectedMsgTest: XCTestCase {
+
+    func testPasswordProtectedMessageCompliance() {
+        let disallowTerms = ["[Classification: Data Control: Internal Data Control]", "droid", "forbidden data"]
+
+        let subjectsToTest: [String: Bool] = [
+            "[Classification: Data Control: Internal Data Control] Quarter results": false,
+            "Conference information [Classification: Data Control: Internal Data Control]": false,
+            "Classification: Data Control: Internal Data Control - Tomorrow meeting": true,
+            "Internal Data Control - Finance monitoring": true,
+            "Android phone update": true,
+            "droid phone": false,
+            "DROiD phone": false,
+            "[forbidden data] year results": false,
+        ]
+
+        for (subject, expectedValue) in subjectsToTest {
+            let result = subject.isPasswordMessageEnabled(disallowTerms: disallowTerms)
+            XCTAssertEqual(result, expectedValue, "Failed for subject: \(subject)")
+        }
+    }
+}

FlowCryptCommon/Extensions/StringExtensions.swift

@@ -158,4 +158,32 @@ public extension String {
         guard parts.count == 2 else { return nil }
         return (String(parts[0]), String(parts[1]))
     }
+
+    func isPasswordMessageEnabled(disallowTerms: [String]) -> Bool {
+        // Allow by default if subject is nil, disallowTerms is empty, or no terms are specified
+        guard disallowTerms.isNotEmpty else {
+            return true
+        }
+
+        let lowerSubject = self.lowercased()
+
+        for term in disallowTerms {
+            // Escape special regex characters
+            let escapedTerm = NSRegularExpression.escapedPattern(for: term)
+
+            // Create regex pattern to ensure term appears as a separate token
+            let pattern = #"(^|\W)\#(escapedTerm)(\W|$)"#
+
+            guard let regex = try? NSRegularExpression(pattern: pattern, options: [.caseInsensitive]) else {
+                continue
+            }
+
+            let range = NSRange(lowerSubject.startIndex..., in: lowerSubject)
+            if regex.firstMatch(in: lowerSubject, range: range) != nil {
+                // Found a disallowed term as a separate token
+                return false
+            }
+        }
+        return true // Allow if no matches are found
+    }
 }