#1306 Add message password policy

.semaphore/semaphore.yml

@@ -5,7 +5,7 @@ agent:
     type: a1-standard-4
     os_image: macos-xcode13
 execution_time_limit:
-  minutes: 90
+  minutes: 120
 auto_cancel:
   running:
     when: branch != 'master'
@@ -15,7 +15,7 @@ blocks:
     run:
       when: 'change_in(''/'', {exclude: [''/Core/package.json'', ''/Core/package-lock.json'']})'
     execution_time_limit:
-      minutes: 85
+      minutes: 115
     task:
       secrets:
         - name: flowcrypt-ios-ci-secrets

FlowCrypt/Controllers/Compose/ComposeViewController.swift

@@ -124,7 +124,9 @@ final class ComposeViewController: TableNodeViewController {
         self.composeMessageService = composeMessageService ?? ComposeMessageService(
             clientConfiguration: clientConfiguration,
             encryptedStorage: appContext.encryptedStorage,
-            messageGateway: appContext.getRequiredMailProvider().messageSender
+            messageGateway: appContext.getRequiredMailProvider().messageSender,
+            passPhraseService: appContext.passPhraseService,
+            sender: email
         )
         self.filesManager = filesManager
         self.photosManager = photosManager
@@ -271,7 +273,6 @@ extension ComposeViewController {
                 let sendableMsg = try await composeMessageService.validateAndProduceSendableMsg(
                     input: input,
                     contextToSend: contextToSend,
-                    email: email,
                     includeAttachments: false,
                     signingPrv: signingPrv
                 )
@@ -507,7 +508,6 @@ extension ComposeViewController {
         let sendableMsg = try await self.composeMessageService.validateAndProduceSendableMsg(
             input: self.input,
             contextToSend: self.contextToSend,
-            email: self.email,
             signingPrv: signingKey
         )
         UIApplication.shared.isIdleTimerDisabled = true
@@ -527,8 +527,17 @@ extension ComposeViewController {
         DispatchQueue.main.asyncAfter(deadline: .now() + hideSpinnerAnimationDuration) { [weak self] in
             guard let self = self else { return }
 
-            if case MessageValidationError.noPubRecipients = error, self.isMessagePasswordSupported {
-                self.setMessagePassword()
+            if self.isMessagePasswordSupported {
+                switch error {
+                case MessageValidationError.noPubRecipients:
+                    self.setMessagePassword()
+                case MessageValidationError.notUniquePassword,
+                    MessageValidationError.subjectContainsPassword,
+                    MessageValidationError.weakPassword:
+                    self.showAlert(message: error.errorMessage)
+                default:
+                    self.showAlert(message: "compose_error".localized + "\n\n" + error.errorMessage)
+                }
             } else {
                 self.showAlert(message: "compose_error".localized + "\n\n" + error.errorMessage)
             }
@@ -1107,7 +1116,9 @@ extension ComposeViewController {
     }
 
     @objc private func messagePasswordTextFieldDidChange(_ sender: UITextField) {
-        messagePasswordAlertController?.actions[1].isEnabled = (sender.text ?? "").isNotEmpty
+        let password = sender.text ?? ""
+        let isPasswordStrong = composeMessageService.isMessagePasswordStrong(pwd: password)
+        messagePasswordAlertController?.actions[1].isEnabled = isPasswordStrong
     }
 }
 

FlowCrypt/Functionality/Error Handling/ErrorHandler.swift

@@ -34,7 +34,7 @@ private struct ComposedErrorHandler: ErrorHandler {
     static let shared: ComposedErrorHandler = ComposedErrorHandler(
         handlers: [
             KeyServiceErrorHandler(),
-            BackupServiceErrorHandler(),
+            BackupServiceErrorHandler()
         ]
     )
 

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

@@ -12,7 +12,10 @@ enum MessageValidationError: Error, CustomStringConvertible, Equatable {
     case emptyRecipient
     case emptySubject
     case emptyMessage
-    case missedPublicKey
+    case weakPassword
+    case subjectContainsPassword
+    case notUniquePassword
+    case missingPublicKey
     case noPubRecipients
     case revokedKeyRecipients
     case expiredKeyRecipients
@@ -27,7 +30,13 @@ enum MessageValidationError: Error, CustomStringConvertible, Equatable {
             return "compose_enter_subject".localized
         case .emptyMessage:
             return "compose_enter_secure".localized
-        case .missedPublicKey:
+        case .weakPassword:
+            return "compose_password_weak".localized
+        case .subjectContainsPassword:
+            return "compose_password_subject_error".localized
+        case .notUniquePassword:
+            return "compose_password_passphrase_error".localized
+        case .missingPublicKey:
             return "compose_no_pub_sender".localized
         case .noPubRecipients:
             return "compose_recipient_no_pub".localized

FlowCrypt/Functionality/Services/Compose Message Service/ComposeMessageService.swift

@@ -22,13 +22,16 @@ protocol CoreComposeMessageType {
 final class ComposeMessageService {
 
     private let messageGateway: MessageGateway
+    private let passPhraseService: PassPhraseServiceType
     private let storage: EncryptedStorageType
     private let contactsService: ContactsServiceType
     private let core: CoreComposeMessageType & KeyParser
     private let enterpriseServer: EnterpriseServerApiType
     private let draftGateway: DraftGateway?
     private lazy var logger: Logger = Logger.nested(Self.self)
 
+    private let sender: String
+
     private struct ReplyInfo: Encodable {
         let sender: String
         let recipient: [String]
@@ -40,12 +43,15 @@ final class ComposeMessageService {
         clientConfiguration: ClientConfiguration,
         encryptedStorage: EncryptedStorageType,
         messageGateway: MessageGateway,
+        passPhraseService: PassPhraseServiceType,
         draftGateway: DraftGateway? = nil,
         contactsService: ContactsServiceType? = nil,
+        sender: String,
         core: CoreComposeMessageType & KeyParser = Core.shared,
         enterpriseServer: EnterpriseServerApiType = EnterpriseServerApi()
     ) {
         self.messageGateway = messageGateway
+        self.passPhraseService = passPhraseService
         self.draftGateway = draftGateway
         self.storage = encryptedStorage
         self.contactsService = contactsService ?? ContactsService(
@@ -54,6 +60,7 @@ final class ComposeMessageService {
         )
         self.core = core
         self.enterpriseServer = enterpriseServer
+        self.sender = sender
         self.logger = Logger.nested(in: Self.self, with: "ComposeMessageService")
     }
 
@@ -66,7 +73,6 @@ final class ComposeMessageService {
     func validateAndProduceSendableMsg(
         input: ComposeMessageInput,
         contextToSend: ComposeMessageContext,
-        email: String,
         includeAttachments: Bool = true,
         signingPrv: PrvKeyInfo?
     ) async throws -> SendableMsg {
@@ -98,8 +104,8 @@ final class ComposeMessageService {
 
         let subject = contextToSend.subject ?? "(no subject)"
 
-        guard let myPubKey = storage.getKeypairs(by: email).map(\.public).first else {
-            throw MessageValidationError.missedPublicKey
+        guard let myPubKey = storage.getKeypairs(by: sender).map(\.public).first else {
+            throw MessageValidationError.missingPublicKey
         }
 
         let sendableAttachments: [SendableMsg.Attachment] = includeAttachments
@@ -114,13 +120,24 @@ final class ComposeMessageService {
         let replyToMimeMsg = input.replyToMime
             .flatMap { String(data: $0, encoding: .utf8) }
 
+        if let password = contextToSend.messagePassword, password.isNotEmpty {
+            if subject.lowercased().contains(password.lowercased()) {
+                throw MessageValidationError.subjectContainsPassword
+            }
+
+            let allAvailablePassPhrases = passPhraseService.getPassPhrases().map(\.value)
+            if allAvailablePassPhrases.contains(password) {
+                throw MessageValidationError.notUniquePassword
+            }
+        }
+
         return SendableMsg(
             text: text,
             html: nil,
             to: recipients.map(\.email),
             cc: [],
             bcc: [],
-            from: email,
+            from: sender,
             subject: subject,
             replyToMimeMsg: replyToMimeMsg,
             atts: sendableAttachments,
@@ -338,4 +355,27 @@ extension ComposeMessageService {
 
         return SendableMsgBody(text: text, html: html)
     }
+
+    func isMessagePasswordStrong(pwd: String) -> Bool {
+        let minLength = 8
+
+        // currently password-protected messages are supported only with FES on iOS
+        // guard enterpriseServer.isFesUsed else {
+        //     // consumers - just 8 chars requirement
+        //     return pwd.count >= minLength
+        // }
+
+        // enterprise FES - use common corporate password rules
+        let predicate = NSPredicate(
+            format: "SELF MATCHES %@ ", [
+                "(?=.*[a-z])", // 1 lowercase character
+                "(?=.*[A-Z])", // 1 uppercase character
+                "(?=.*[0-9])", // 1 number
+                "(?=.*[\\-@$#!%*?&_,;:'()\"])", // 1 special symbol
+                ".{\(minLength),}$" // minimum 8 characters
+            ].joined()
+        )
+
+        return predicate.evaluate(with: pwd)
+    }
 }

FlowCrypt/Resources/en.lproj/Localizable.strings

@@ -82,10 +82,13 @@
 "compose_recipient_revoked" = "One or more of your recipients have revoked public keys (marked in red).\n\nPlease ask them to send you a new public key. If this is an enterprise installation, please ask your systems admin.";
 "compose_recipient_expired" = "One or more of your recipients have expired public keys (marked in orange).\n\nPlease ask them to send you updated public key. If this is an enterprise installation, please ask your systems admin.";
 "compose_recipient_invalid_email" = "One or more of your recipients have invalid email address (marked in red)";
+"compose_password_weak" = "Password didn't comply with company policy, which requires at least:\n\n- one uppercase\n- one lowercase\n- one number\n- one special character eg &/#\"-'_%-@,;:!*()\n- 8 characters length\n\nPlease update the password and re-send.";
+"compose_password_passphrase_error" = "Please do not use your private key pass phrase as a password for this message.\n\nYou should come up with some other unique password that you can share with recipient.";
+"compose_password_subject_error" = "Please do not include the password in the email subject. Sharing password over email undermines password based encryption.\n\nYou can ask the recipient to also install FlowCrypt, messages between FlowCrypt users don't need a password.";
 "compose_password_placeholder" = "Tap to add password for recipients who don't have encryption set up.";
 "compose_password_set_message" = "Web portal password added";
 "compose_password_modal_title" = "Set web portal password";
-"compose_password_modal_message" = "The recipients will receive a link to read your message on a web portal, where they will need to enter this password.\n\nYou are responsible for sharing this password with recipients (use other medium to share the password - not email)";
+"compose_password_modal_message" = "The recipients will receive a link to read your message on a web portal, where they will need to enter this password.\n\nYou are responsible for sharing this password with recipients (use other medium to share the password - not email)\n\nPassword should include:\n- one uppercase\n- one lowercase\n- one number\n- one special character eg &/#\"-'_%-@,;:!*()\n- min 8 characters length";
 "compose_error" = "Could not compose message";
 "compose_reply_successful" = "Reply successfully sent";
 "compose_quote_from" = "On %@ at %@ %@ wrote:"; // Date, time, sender

FlowCryptAppTests/ExtensionTests.swift

@@ -82,11 +82,12 @@ extension ExtensionTests {
         dateFormatter.dateFormat = "HH:mm"
 
         let today = Date()
-        let year = Calendar.current.dateComponents([.year], from: today).year
+        let components = Calendar.current.dateComponents([.year, .day], from: today)
+
         let sameYearDate = try XCTUnwrap(DateComponents(
             calendar: .current,
             timeZone: .current,
-            year: year,
+            year: components.year,
             month: 1,
             day: 24,
             hour: 18,