Fix

* Add protocol requirements

* Load auth settings.

* Updates.

* Update preview store

* Add lock icon

.github/workflows/nightly.yml

@@ -0,0 +1,49 @@
+name: Nightly
+
+on: 
+  schedule: 
+    - cron: "0 8 * * *"
+jobs:
+  build:
+    runs-on: macos-11.0
+    timeout-minutes: 10
+    steps:
+    - uses: actions/checkout@v2
+    - name: Setup Signing
+      env: 
+        SIGNING_DATA: ${{ secrets.SIGNING_DATA }}
+        SIGNING_PASSWORD: ${{ secrets.SIGNING_PASSWORD }}
+        HOST_PROFILE_DATA: ${{ secrets.HOST_PROFILE_DATA }}
+        AGENT_PROFILE_DATA: ${{ secrets.AGENT_PROFILE_DATA }}
+        APPLE_API_KEY_DATA: ${{ secrets.APPLE_API_KEY_DATA }}
+        APPLE_API_KEY_ID: ${{ secrets.APPLE_API_KEY_ID }}
+      run: ./.github/scripts/signing.sh
+    - name: Set Environment
+      run: sudo xcrun xcode-select -s /Applications/Xcode_13.2.1.app
+    - name: Update Build Number
+      env:
+        RUN_ID: ${{ github.run_id }}
+      run: |
+            sed -i '' -e "s/GITHUB_CI_VERSION/0.0.0/g" Sources/Config/Config.xcconfig
+            sed -i '' -e "s/GITHUB_BUILD_NUMBER/1.$RUN_ID/g" Sources/Config/Config.xcconfig
+            sed -i '' -e "s/GITHUB_BUILD_URL/https:\/\/github.com\/maxgoedjen\/secretive\/actions\/runs\/$RUN_ID/g" Sources/Secretive/Credits.rtf
+    - name: Build
+      run: xcrun xcodebuild -project Sources/Secretive.xcodeproj -scheme Secretive -configuration Release -archivePath Archive.xcarchive archive
+    - name: Create ZIPs
+      run: |
+            ditto -c -k --sequesterRsrc --keepParent Archive.xcarchive/Products/Applications/Secretive.app ./Secretive.zip
+            ditto -c -k --sequesterRsrc --keepParent Archive.xcarchive ./Archive.zip
+    - name: Notarize
+      env: 
+        APPLE_API_KEY_ID: ${{ secrets.APPLE_API_KEY_ID }}
+        APPLE_API_ISSUER: ${{ secrets.APPLE_API_ISSUER }}
+      run: xcrun notarytool submit --key ~/.private_keys/AuthKey_$APPLE_API_KEY_ID.p8 --key-id $APPLE_API_KEY_ID --issuer $APPLE_API_ISSUER Secretive.zip
+    - name: Document SHAs
+      run: |
+            shasum -a 512 Secretive.zip
+            shasum -a 512 Archive.zip
+    - name: Upload App to Artifacts
+      uses: actions/upload-artifact@v1
+      with:
+        name: Secretive.zip
+        path: Secretive.zip

APP_CONFIG.md

@@ -51,6 +51,30 @@ Add this to `~/Library/LaunchAgents/com.maxgoedjen.Secretive.SecretAgent.plist`
 
 Log out and log in again before launching Cyberduck.
 
+## GitKraken
+
+Add this to `~/Library/LaunchAgents/com.maxgoedjen.Secretive.SecretAgent.plist`
+
+```
+<?xml version="1.0" encoding="UTF-8"?>
+<!DOCTYPE plist PUBLIC "-//Apple//DTD PLIST 1.0//EN" "http://www.apple.com/DTDs/PropertyList-1.0.dtd">
+<plist version="1.0">
+<dict>
+  <key>Label</key>
+  <string>link-ssh-auth-sock</string>
+  <key>ProgramArguments</key>
+  <array>
+    <string>/bin/sh</string>
+    <string>-c</string>
+    <string>/bin/ln -sf $HOME/Library/Containers/com.maxgoedjen.Secretive.SecretAgent/Data/socket.ssh $SSH_AUTH_SOCK</string>
+  </array>
+  <key>RunAtLoad</key>
+  <true/>
+</dict>
+</plist>
+```
+
+Log out and log in again before launching Gitkraken. Then enable "Use local SSH agent in GitKraken Preferences (Located under Preferences -> SSH)
 
 # The app I use isn't listed here!
 

FAQ.md

@@ -26,7 +26,11 @@ Please run `ssh -Tv git@github.com` in your terminal and paste the output in a [
 
 ### How do I tell SSH to use a specific key?
 
-You can create a `mykey.pub` (where `mykey` is the name of your key) in your `~/.ssh/` directory with the contents of your public key, and specify that you want to use that key in your `~/.ssh/config`.  [This ServerFault answer](https://serverfault.com/a/295771) has more details on setting that up
+Beginning with Secretive 2.2, every secret has an automatically generated public key file representation on disk, and the path to it is listed under "Public Key Path" in Secretive. You can specify that you want to use that key in your `~/.ssh/config`.  [This ServerFault answer](https://serverfault.com/a/295771) has more details on setting that up.
+
+### Can I use Secretive for SSH Agent Forwarding?
+
+Yes, you can! Once you've set up Secretive, just add `ForwardAgent yes` to the hosts you want to forward to in your SSH config file. Afterwards, any use of one of your SSH keys on the remote host must be authenticated through Secretive.
 
 ### Why should I trust you?
 
@@ -40,6 +44,10 @@ Awesome! Just bear in mind that because an app only has access to the keychain i
 
 Secretive checks in with GitHub's releases API to check if there's a new version of Secretive available. You can audit the source code for this feature [here](https://github.com/maxgoedjen/secretive/blob/main/Sources/Packages/Sources/Brief/Updater.swift).
 
+### How do I uninstall Secretive?
+
+Drag Secretive.app to the trash and remove `~/Library/Containers/com.maxgoedjen.Secretive.SecretAgent`. `SecretAgent` may continue running until you quit it or reboot.
+
 ### I have a security issue
 
 Please contact [max.goedjen@gmail.com](mailto:max.goedjen@gmail.com) with a subject containing "SECRETIVE SECURITY" immediately with details, and I'll address the issue and credit you ASAP.

README.md

@@ -16,13 +16,13 @@ The most common setup for SSH keys is just keeping them on disk, guarded by prop
 
 If your Mac has a Secure Enclave, it also has support for strong access controls like Touch ID, or authentication with Apple Watch. You can configure your key so that they require Touch ID (or Watch) authentication before they're accessed.
 
-<img src="/.github/readme/touchid.png" alt="Screenshot of Secretive authenticating with Touch ID">
+<img src="/.github/readme/touchid.png" alt="Screenshot of Secretive authenticating with Touch ID" width="400">
 
 ### Notifications
 
 Secretive also notifies you whenever your keys are accessed, so you're never caught off guard.
 
-<img src="/.github/readme/notification.png" alt="Screenshot of Secretive notifying the user">
+<img src="/.github/readme/notification.png" alt="Screenshot of Secretive notifying the user" width="600">
 
 ### Support for Smart Cards Too!
 

Sources/Packages/Sources/SecretAgentKit/Agent.swift

@@ -30,20 +30,23 @@ extension Agent {
     /// - Parameters:
     ///   - reader: A ``FileHandleReader`` to read the content of the request.
     ///   - writer: A ``FileHandleWriter`` to write the response to.
-    public func handle(reader: FileHandleReader, writer: FileHandleWriter) {
+    /// - Return value: 
+    ///   - Boolean if data could be read
+    @discardableResult public func handle(reader: FileHandleReader, writer: FileHandleWriter) -> Bool {
         Logger().debug("Agent handling new data")
         let data = Data(reader.availableData)
-        guard data.count > 4 else { return }
+        guard data.count > 4 else { return false}
         let requestTypeInt = data[4]
         guard let requestType = SSHAgent.RequestType(rawValue: requestTypeInt) else {
             writer.write(OpenSSHKeyWriter().lengthAndData(of: SSHAgent.ResponseType.agentFailure.data))
             Logger().debug("Agent returned \(SSHAgent.ResponseType.agentFailure.debugDescription)")
-            return
+            return true
         }
         Logger().debug("Agent handling request of type \(requestType.debugDescription)")
         let subData = Data(data[5...])
         let response = handle(requestType: requestType, data: subData, reader: reader)
         writer.write(response)
+        return true
     }
 
     func handle(requestType: SSHAgent.RequestType, data: Data, reader: FileHandleReader) -> Data {
@@ -110,7 +113,7 @@ extension Agent {
 
         let dataToSign = reader.readNextChunk()
         let signed = try store.sign(data: dataToSign, with: secret, for: provenance)
-        let derSignature = signed.data
+        let derSignature = signed
 
         let curveData = writer.curveType(for: secret.algorithm, length: secret.keySize).data(using: .utf8)!
 
@@ -151,7 +154,7 @@ extension Agent {
         signedData.append(writer.lengthAndData(of: sub))
 
         if let witness = witness {
-            try witness.witness(accessTo: secret, from: store, by: provenance, requiredAuthentication: signed.requiredAuthentication)
+            try witness.witness(accessTo: secret, from: store, by: provenance)
         }
 
         Logger().debug("Agent signed request")

Sources/Packages/Sources/SecretAgentKit/SigningWitness.swift

@@ -17,7 +17,6 @@ public protocol SigningWitness {
     ///   - secret: The `Secret` that will was used to sign the request.
     ///   - store: The `Store` that signed the request..
     ///   - provenance: A `SigningRequestProvenance` object describing the origin of the request.
-    ///   - requiredAuthentication: A boolean describing whether or not authentication was required for the request.
-    func witness(accessTo secret: AnySecret, from store: AnySecretStore, by provenance: SigningRequestProvenance, requiredAuthentication: Bool) throws
+    func witness(accessTo secret: AnySecret, from store: AnySecretStore, by provenance: SigningRequestProvenance) throws
 
 }

Sources/Packages/Sources/SecretAgentKit/SocketController.swift

@@ -9,7 +9,9 @@ public class SocketController {
     /// The active SocketPort.
     private var port: SocketPort?
     /// A handler that will be notified when a new read/write handle is available.
-    public var handler: ((FileHandleReader, FileHandleWriter) -> Void)?
+    /// False if no data could be read
+    public var handler: ((FileHandleReader, FileHandleWriter) -> Bool)?
+
 
     /// Initializes a socket controller with a specified path.
     /// - Parameter path: The path to use as a socket.
@@ -43,20 +45,14 @@ public class SocketController {
         var addr = sockaddr_un()
         addr.sun_family = sa_family_t(AF_UNIX)
 
-        var len: Int = 0
+        let len = MemoryLayout.size(ofValue: addr.sun_path) - 1
         withUnsafeMutablePointer(to: &addr.sun_path.0) { pointer in
-            path.withCString { cstring in
-                len = strlen(cstring)
-                strncpy(pointer, cstring, len)
-            }
-        }
-        addr.sun_len = UInt8(len+2)
-
-        var data: Data!
-        withUnsafePointer(to: &addr) { pointer in
-            data = Data(bytes: pointer, count: MemoryLayout<sockaddr_un>.size)
+            // The buffer is pre-zeroed, so manual termination is unnecessary.
+            precondition(memccpy(pointer, path, 0, len) != nil)
         }
+        addr.sun_len = UInt8(len)
 
+        let data = withUnsafeBytes(of: &addr, Data.init(_:))
         return SocketPort(protocolFamily: AF_UNIX, socketType: SOCK_STREAM, protocol: 0, address: data)!
     }
 
@@ -65,7 +61,7 @@ public class SocketController {
     @objc func handleConnectionAccept(notification: Notification) {
         Logger().debug("Socket controller accepted connection")
         guard let new = notification.userInfo?[NSFileHandleNotificationFileHandleItem] as? FileHandle else { return }
-        handler?(new, new)
+        _ = handler?(new, new)
         new.waitForDataInBackgroundAndNotify()
         fileHandle?.acceptConnectionInBackgroundAndNotify(forModes: [RunLoop.current.currentMode!])
     }
@@ -76,7 +72,12 @@ public class SocketController {
         Logger().debug("Socket controller has new data available")
         guard let new = notification.object as? FileHandle else { return }
         Logger().debug("Socket controller received new file handle")
-        handler?(new, new)
+        if((handler?(new, new)) == true) {
+            Logger().debug("Socket controller handled data, wait for more data")
+            new.waitForDataInBackgroundAndNotify()
+        } else {
+            Logger().debug("Socket controller called with empty data, socked closed")
+        }
     }
 
 }

Sources/Packages/Sources/SecretKit/Documentation.docc/Documentation.md

@@ -27,5 +27,8 @@ SecretKit is a collection of protocols describing secrets and stores.
 
 ### Signing Process
 
-- ``SignedData``
 - ``SigningRequestProvenance``
+
+### Authentication Persistence
+
+- ``PersistedAuthenticationContext``

Sources/Packages/Sources/SecretKit/Erasers/AnySecret.swift

@@ -9,6 +9,7 @@ public struct AnySecret: Secret {
     private let _name: () -> String
     private let _algorithm: () -> Algorithm
     private let _keySize: () -> Int
+    private let _requiresAuthentication: () -> Bool
     private let _publicKey: () -> Data
 
     public init<T>(_ secret: T) where T: Secret {
@@ -19,6 +20,7 @@ public struct AnySecret: Secret {
             _name = secret._name
             _algorithm = secret._algorithm
             _keySize = secret._keySize
+            _requiresAuthentication = secret._requiresAuthentication
             _publicKey = secret._publicKey
         } else {
             base = secret as Any
@@ -27,6 +29,7 @@ public struct AnySecret: Secret {
             _name = { secret.name }
             _algorithm = { secret.algorithm }
             _keySize = { secret.keySize }
+            _requiresAuthentication = { secret.requiresAuthentication }
             _publicKey = { secret.publicKey }
         }
     }
@@ -47,6 +50,10 @@ public struct AnySecret: Secret {
         _keySize()
     }
 
+    public var requiresAuthentication: Bool {
+        _requiresAuthentication()
+    }
+
     public var publicKey: Data {
         _publicKey()
     }

Sources/Packages/Sources/SecretKit/Erasers/AnySecretStore.swift

@@ -9,7 +9,8 @@ public class AnySecretStore: SecretStore {
     private let _id: () -> UUID
     private let _name: () -> String
     private let _secrets: () -> [AnySecret]
-    private let _sign: (Data, AnySecret, SigningRequestProvenance) throws -> SignedData
+    private let _sign: (Data, AnySecret, SigningRequestProvenance) throws -> Data
+    private let _existingPersistedAuthenticationContext: (AnySecret) -> PersistedAuthenticationContext?
     private let _persistAuthentication: (AnySecret, TimeInterval) throws -> Void
 
     private var sink: AnyCancellable?
@@ -21,6 +22,7 @@ public class AnySecretStore: SecretStore {
         _id = { secretStore.id }
         _secrets = { secretStore.secrets.map { AnySecret($0) } }
         _sign = { try secretStore.sign(data: $0, with: $1.base as! SecretStoreType.SecretType, for: $2) }
+        _existingPersistedAuthenticationContext = { secretStore.existingPersistedAuthenticationContext(secret: $0.base as! SecretStoreType.SecretType) }
         _persistAuthentication = { try secretStore.persistAuthentication(secret: $0.base as! SecretStoreType.SecretType, forDuration: $1) }
         sink = secretStore.objectWillChange.sink { _ in
             self.objectWillChange.send()
@@ -43,10 +45,14 @@ public class AnySecretStore: SecretStore {
         return _secrets()
     }
 
-    public func sign(data: Data, with secret: AnySecret, for provenance: SigningRequestProvenance) throws -> SignedData {
+    public func sign(data: Data, with secret: AnySecret, for provenance: SigningRequestProvenance) throws -> Data {
         try _sign(data, secret, provenance)
     }
 
+    public func existingPersistedAuthenticationContext(secret: AnySecret) -> PersistedAuthenticationContext? {
+        _existingPersistedAuthenticationContext(secret)
+    }
+
     public func persistAuthentication(secret: AnySecret, forDuration duration: TimeInterval) throws {
         try _persistAuthentication(secret, duration)
     }

Sources/Packages/Sources/SecretKit/PublicKeyStandinFileController.swift

@@ -6,6 +6,7 @@ public class PublicKeyFileStoreController {
 
     private let logger = Logger()
     private let directory: String
+    private let keyWriter = OpenSSHKeyWriter()
 
     /// Initializes a PublicKeyFileStoreController.
     public init(homeDirectory: String) {
@@ -21,7 +22,6 @@ public class PublicKeyFileStoreController {
             try? FileManager.default.removeItem(at: URL(fileURLWithPath: directory))
         }
         try? FileManager.default.createDirectory(at: URL(fileURLWithPath: directory), withIntermediateDirectories: false, attributes: nil)
-        let keyWriter = OpenSSHKeyWriter()
         for secret in secrets {
             let path = path(for: secret)
             guard let data = keyWriter.openSSHString(secret: secret).data(using: .utf8) else { continue }
@@ -35,7 +35,8 @@ public class PublicKeyFileStoreController {
     /// - Returns: The path to the Secret's public key.
     /// - Warning: This method returning a path does not imply that a key has been written to disk already. This method only describes where it will be written to.
     public func path<SecretType: Secret>(for secret: SecretType) -> String {
-        directory.appending("/").appending("\(secret.name.replacingOccurrences(of: " ", with: "-")).pub")
+        let minimalHex = keyWriter.openSSHMD5Fingerprint(secret: secret).replacingOccurrences(of: ":", with: "")
+        return directory.appending("/").appending("\(minimalHex).pub")
     }
 
 }

Sources/Packages/Sources/SecretKit/Types/PersistedAuthenticationContext.swift

@@ -0,0 +1,9 @@
+import Foundation
+
+/// Protocol describing a persisted authentication context. This is an authorization that can be reused for multiple access to a secret that requires authentication for a specific period of time.
+public protocol PersistedAuthenticationContext {
+    /// Whether the context remains valid.
+    var valid: Bool { get }
+    /// The date at which the authorization expires and the context becomes invalid.
+    var expiration: Date { get }
+}

Sources/Packages/Sources/SecretKit/Types/Secret.swift

@@ -9,6 +9,8 @@ public protocol Secret: Identifiable, Hashable {
     var algorithm: Algorithm { get }
     /// The key size for the secret.
     var keySize: Int { get }
+    /// Whether the secret requires authentication before use.
+    var requiresAuthentication: Bool { get }
     /// The public key data for the secret.
     var publicKey: Data { get }
 

Sources/Packages/Sources/SecretKit/Types/SecretStore.swift

@@ -20,8 +20,14 @@ public protocol SecretStore: ObservableObject, Identifiable {
     ///   - data: The data to sign.
     ///   - secret: The ``Secret`` to sign with.
     ///   - provenance: A ``SigningRequestProvenance`` describing where the request came from.
-    /// - Returns: A ``SignedData`` object, containing the signature and metadata about the signature process.
-    func sign(data: Data, with secret: SecretType, for provenance: SigningRequestProvenance) throws -> SignedData
+    /// - Returns: The signed data.
+    func sign(data: Data, with secret: SecretType, for provenance: SigningRequestProvenance) throws -> Data
+
+    /// Checks to see if there is currently a valid persisted authentication for a given secret.
+    /// - Parameters:
+    ///   - secret: The ``Secret`` to check if there is a persisted authentication for.
+    /// - Returns: A persisted authentication context, if a valid one exists.
+    func existingPersistedAuthenticationContext(secret: SecretType) -> PersistedAuthenticationContext?
 
     /// Persists user authorization for access to a secret.
     /// - Parameters:
@@ -56,6 +62,9 @@ public protocol SecretStoreModifiable: SecretStore {
 
 extension NSNotification.Name {
 
+    // Distributed notification that keys were modified out of process (ie, that the management tool added/removed secrets)
     public static let secretStoreUpdated = NSNotification.Name("com.maxgoedjen.Secretive.secretStore.updated")
+    // Internal notification that keys were reloaded from the backing store.
+    public static let secretStoreReloaded = NSNotification.Name("com.maxgoedjen.Secretive.secretStore.reloaded")
 
 }

Sources/Packages/Sources/SecretKit/Types/SignedData.swift

@@ -1,20 +0,0 @@
-import Foundation
-
-/// Describes the output of a sign request.
-public struct SignedData {
-
-    /// The signed data.
-    public let data: Data
-    /// A boolean describing whether authentication was required during the signature process.
-    public let requiredAuthentication: Bool
-
-    /// Initializes a new SignedData.
-    /// - Parameters:
-    ///   - data: The signed data.
-    ///   - requiredAuthentication: A boolean describing whether authentication was required during the signature process.
-    public init(data: Data, requiredAuthentication: Bool) {
-        self.data = data
-        self.requiredAuthentication = requiredAuthentication
-    }
-
-}

Sources/Packages/Sources/SecureEnclaveSecretKit/SecureEnclaveSecret.swift

@@ -11,6 +11,7 @@ extension SecureEnclave {
         public let name: String
         public let algorithm = Algorithm.ellipticCurve
         public let keySize = 256
+        public let requiresAuthentication: Bool
         public let publicKey: Data
 
     }

Sources/Packages/Sources/SecureEnclaveSecretKit/SecureEnclaveStore.swift

@@ -24,7 +24,7 @@ extension SecureEnclave {
         /// Initializes a Store.
         public init() {
             DistributedNotificationCenter.default().addObserver(forName: .secretStoreUpdated, object: nil, queue: .main) { _ in
-                self.reloadSecrets(notify: false)
+                self.reloadSecrets(notifyAgent: false)
             }
             loadSecrets()
         }
@@ -100,7 +100,7 @@ extension SecureEnclave {
             reloadSecrets()
         }
         
-        public func sign(data: Data, with secret: SecretType, for provenance: SigningRequestProvenance) throws -> SignedData {
+        public func sign(data: Data, with secret: SecretType, for provenance: SigningRequestProvenance) throws -> Data {
             let context: LAContext
             if let existing = persistedAuthenticationContexts[secret], existing.valid {
                 context = existing.context
@@ -131,16 +131,15 @@ extension SecureEnclave {
             let key = untypedSafe as! SecKey
             var signError: SecurityError?
 
-            let signingStartTime = Date()
             guard let signature = SecKeyCreateSignature(key, .ecdsaSignatureMessageX962SHA256, data as CFData, &signError) else {
                 throw SigningError(error: signError)
             }
-            let signatureDuration = Date().timeIntervalSince(signingStartTime)
-            // Hack to determine if the user had to authenticate to sign.
-            // Since there's now way to inspect SecAccessControl to determine (afaict).
-            let requiredAuthentication = signatureDuration > Constants.unauthenticatedThreshold
+            return signature as Data
+        }
 
-            return SignedData(data: signature as Data, requiredAuthentication: requiredAuthentication)
+        public func existingPersistedAuthenticationContext(secret: Secret) -> PersistedAuthenticationContext? {
+            guard let persisted = persistedAuthenticationContexts[secret], persisted.valid else { return nil }
+            return persisted
         }
 
         public func persistAuthentication(secret: Secret, forDuration duration: TimeInterval) throws {
@@ -171,18 +170,19 @@ extension SecureEnclave {
 extension SecureEnclave.Store {
 
     /// Reloads all secrets from the store.
-    /// - Parameter notify: A boolean indicating whether a distributed notification should be posted, notifying other processes (ie, the SecretAgent) to reload their stores as well.
-    private func reloadSecrets(notify: Bool = true) {
+    /// - Parameter notifyAgent: A boolean indicating whether a distributed notification should be posted, notifying other processes (ie, the SecretAgent) to reload their stores as well.
+    private func reloadSecrets(notifyAgent: Bool = true) {
         secrets.removeAll()
         loadSecrets()
-        if notify {
-            DistributedNotificationCenter.default().post(name: .secretStoreUpdated, object: nil)
+        NotificationCenter.default.post(name: .secretStoreReloaded, object: self)
+        if notifyAgent {
+            DistributedNotificationCenter.default().postNotificationName(.secretStoreUpdated, object: nil, deliverImmediately: true)
         }
     }
 
     /// Loads all secrets from the store.
     private func loadSecrets() {
-        let attributes = [
+        let publicAttributes = [
             kSecClass: kSecClassKey,
             kSecAttrKeyType: SecureEnclave.Constants.keyType,
             kSecAttrApplicationTag: SecureEnclave.Constants.keyTag,
@@ -191,16 +191,46 @@ extension SecureEnclave.Store {
             kSecMatchLimit: kSecMatchLimitAll,
             kSecReturnAttributes: true
             ] as CFDictionary
-        var untyped: CFTypeRef?
-        SecItemCopyMatching(attributes, &untyped)
-        guard let typed = untyped as? [[CFString: Any]] else { return }
-        let wrapped: [SecureEnclave.Secret] = typed.map {
+        var publicUntyped: CFTypeRef?
+        SecItemCopyMatching(publicAttributes, &publicUntyped)
+        guard let publicTyped = publicUntyped as? [[CFString: Any]] else { return }
+        let privateAttributes = [
+            kSecClass: kSecClassKey,
+            kSecAttrKeyType: SecureEnclave.Constants.keyType,
+            kSecAttrApplicationTag: SecureEnclave.Constants.keyTag,
+            kSecAttrKeyClass: kSecAttrKeyClassPrivate,
+            kSecReturnRef: true,
+            kSecMatchLimit: kSecMatchLimitAll,
+            kSecReturnAttributes: true
+            ] as CFDictionary
+        var privateUntyped: CFTypeRef?
+        SecItemCopyMatching(privateAttributes, &privateUntyped)
+        guard let privateTyped = privateUntyped as? [[CFString: Any]] else { return }
+        let privateMapped = privateTyped.reduce(into: [:] as [Data: [CFString: Any]]) { partialResult, next in
+            let id = next[kSecAttrApplicationLabel] as! Data
+            partialResult[id] = next
+        }
+        let authNotRequiredAccessControl: SecAccessControl =
+            SecAccessControlCreateWithFlags(kCFAllocatorDefault,
+                                            kSecAttrAccessibleWhenUnlockedThisDeviceOnly,
+                                            [.privateKeyUsage],
+                                            nil)!
+
+        let wrapped: [SecureEnclave.Secret] = publicTyped.map {
             let name = $0[kSecAttrLabel] as? String ?? "Unnamed"
             let id = $0[kSecAttrApplicationLabel] as! Data
             let publicKeyRef = $0[kSecValueRef] as! SecKey
             let publicKeyAttributes = SecKeyCopyAttributes(publicKeyRef) as! [CFString: Any]
             let publicKey = publicKeyAttributes[kSecValueData] as! Data
-            return SecureEnclave.Secret(id: id, name: name, publicKey: publicKey)
+            let privateKey = privateMapped[id]
+            let requiresAuth: Bool
+            if let authRequirements = privateKey?[kSecAttrAccessControl] {
+                // Unfortunately we can't inspect the access control object directly, but it does behave predicatable with equality.
+                requiresAuth = authRequirements as! SecAccessControl != authNotRequiredAccessControl
+            } else {
+                requiresAuth = false
+            }
+            return SecureEnclave.Secret(id: id, name: name, requiresAuthentication: requiresAuth, publicKey: publicKey)
         }
         secrets.append(contentsOf: wrapped)
     }
@@ -263,7 +293,7 @@ extension SecureEnclave {
 extension SecureEnclave {
 
     /// A context describing a persisted authentication.
-    private struct PersistentAuthenticationContext {
+    private struct PersistentAuthenticationContext: PersistedAuthenticationContext {
 
         /// The Secret to persist authentication for.
         let secret: Secret
@@ -271,7 +301,7 @@ extension SecureEnclave {
         let context: LAContext
         /// An expiration date for the context.
         /// - Note -  Monotonic time instead of Date() to prevent people setting the clock back.
-        let expiration: UInt64
+        let monotonicExpiration: UInt64
 
         /// Initializes a context.
         /// - Parameters:
@@ -282,12 +312,18 @@ extension SecureEnclave {
             self.secret = secret
             self.context = context
             let durationInNanoSeconds = Measurement(value: duration, unit: UnitDuration.seconds).converted(to: .nanoseconds).value
-            self.expiration = clock_gettime_nsec_np(CLOCK_MONOTONIC) + UInt64(durationInNanoSeconds)
+            self.monotonicExpiration = clock_gettime_nsec_np(CLOCK_MONOTONIC) + UInt64(durationInNanoSeconds)
         }
 
         /// A boolean describing whether or not the context is still valid.
         var valid: Bool {
-            clock_gettime_nsec_np(CLOCK_MONOTONIC) < expiration
+            clock_gettime_nsec_np(CLOCK_MONOTONIC) < monotonicExpiration
+        }
+
+        var expiration: Date {
+            let remainingNanoseconds = monotonicExpiration - clock_gettime_nsec_np(CLOCK_MONOTONIC)
+            let remainingInSeconds = Measurement(value: Double(remainingNanoseconds), unit: UnitDuration.nanoseconds).converted(to: .seconds).value
+            return Date(timeIntervalSinceNow: remainingInSeconds)
         }
     }
 

Sources/Packages/Sources/SmartCardSecretKit/SmartCardSecret.swift

@@ -11,6 +11,7 @@ extension SmartCard {
         public let name: String
         public let algorithm: Algorithm
         public let keySize: Int
+        public let requiresAuthentication: Bool = false
         public let publicKey: Data
 
     }

Sources/Packages/Sources/SmartCardSecretKit/SmartCardStore.swift

@@ -44,7 +44,7 @@ extension SmartCard {
             fatalError("Keys must be deleted on the smart card.")
         }
 
-        public func sign(data: Data, with secret: SecretType, for provenance: SigningRequestProvenance) throws -> SignedData {
+        public func sign(data: Data, with secret: SecretType, for provenance: SigningRequestProvenance) throws -> Data {
             guard let tokenID = tokenID else { fatalError() }
             let context = LAContext()
             context.localizedReason = "sign a request from \"\(provenance.origin.displayName)\" using secret \"\(secret.name)\""
@@ -79,7 +79,11 @@ extension SmartCard {
             guard let signature = SecKeyCreateSignature(key, signatureAlgorithm, data as CFData, &signError) else {
                 throw SigningError(error: signError)
             }
-            return SignedData(data: signature as Data, requiredAuthentication: false)
+            return signature as Data
+        }
+
+        public func existingPersistedAuthenticationContext(secret: SmartCard.Secret) -> PersistedAuthenticationContext? {
+            nil
         }
 
         public func persistAuthentication(secret: SmartCard.Secret, forDuration: TimeInterval) throws {

Sources/Packages/Tests/SecretAgentKitTests/StubStore.swift

@@ -49,7 +49,7 @@ extension Stub {
             print("Public Key OpenSSH: \(OpenSSHKeyWriter().openSSHString(secret: secret))")
         }
 
-        public func sign(data: Data, with secret: Secret, for provenance: SigningRequestProvenance) throws -> SignedData {
+        public func sign(data: Data, with secret: Secret, for provenance: SigningRequestProvenance) throws -> Data {
             guard !shouldThrow else {
                 throw NSError(domain: "test", code: 0, userInfo: nil)
             }
@@ -68,7 +68,11 @@ extension Stub {
             default:
                 fatalError()
             }
-            return SignedData(data: SecKeyCreateSignature(privateKey, signatureAlgorithm, data as CFData, nil)! as Data, requiredAuthentication: false)
+            return SecKeyCreateSignature(privateKey, signatureAlgorithm, data as CFData, nil)! as Data
+        }
+
+        public func existingPersistedAuthenticationContext(secret: Stub.Secret) -> PersistedAuthenticationContext? {
+            nil
         }
 
         public func persistAuthentication(secret: Stub.Secret, forDuration duration: TimeInterval) throws {
@@ -88,6 +92,7 @@ extension Stub {
 
         let keySize: Int
         let publicKey: Data
+        let requiresAuthentication = false
         let privateKey: Data
 
         init(keySize: Int, publicKey: Data, privateKey: Data) {

Sources/Packages/Tests/SecretAgentKitTests/StubWitness.swift

@@ -17,7 +17,7 @@ func speakNowOrForeverHoldYourPeace(forAccessTo secret: AnySecret, from store: A
         }
     }
 
-func witness(accessTo secret: AnySecret, from store: AnySecretStore, by provenance: SigningRequestProvenance, requiredAuthentication: Bool) throws {
+func witness(accessTo secret: AnySecret, from store: AnySecretStore, by provenance: SigningRequestProvenance) throws {
         witness(secret, provenance)
     }
 

Sources/SecretAgent/AppDelegate.swift

@@ -33,7 +33,7 @@ class AppDelegate: NSObject, NSApplicationDelegate {
         DispatchQueue.main.async {
             self.socketController.handler = self.agent.handle(reader:writer:)
         }
-        DistributedNotificationCenter.default().addObserver(forName: .secretStoreUpdated, object: nil, queue: .main) { [self] _ in
+        NotificationCenter.default.addObserver(forName: .secretStoreReloaded, object: nil, queue: .main) { [self] _ in
             try? publicKeyFileStoreController.generatePublicKeys(for: storeList.stores.flatMap({ $0.secrets }), clear: true)
         }
         try? publicKeyFileStoreController.generatePublicKeys(for: storeList.stores.flatMap({ $0.secrets }), clear: true)

Sources/SecretAgent/Notifier.swift

@@ -57,7 +57,7 @@ class Notifier {
         notificationCenter.requestAuthorization(options: .alert) { _, _ in }
     }
 
-    func notify(accessTo secret: AnySecret, from store: AnySecretStore, by provenance: SigningRequestProvenance, requiredAuthentication: Bool) {
+    func notify(accessTo secret: AnySecret, from store: AnySecretStore, by provenance: SigningRequestProvenance) {
         notificationDelegate.pendingPersistableSecrets[secret.id.description] = secret
         notificationDelegate.pendingPersistableStores[store.id.description] = store
         let notificationCenter = UNUserNotificationCenter.current()
@@ -69,7 +69,7 @@ class Notifier {
         if #available(macOS 12.0, *) {
             notificationContent.interruptionLevel = .timeSensitive
         }
-        if requiredAuthentication {
+        if secret.requiresAuthentication && store.existingPersistedAuthenticationContext(secret: secret) == nil {
             notificationContent.categoryIdentifier = Constants.persistAuthenticationCategoryIdentitifier
         }
         if let iconURL = provenance.origin.iconURL, let attachment = try? UNNotificationAttachment(identifier: "icon", url: iconURL, options: nil) {
@@ -106,8 +106,8 @@ extension Notifier: SigningWitness {
     func speakNowOrForeverHoldYourPeace(forAccessTo secret: AnySecret, from store: AnySecretStore, by provenance: SigningRequestProvenance) throws {
     }
 
-    func witness(accessTo secret: AnySecret, from store: AnySecretStore, by provenance: SigningRequestProvenance, requiredAuthentication: Bool) throws {
-        notify(accessTo: secret, from: store, by: provenance, requiredAuthentication: requiredAuthentication)
+    func witness(accessTo secret: AnySecret, from store: AnySecretStore, by provenance: SigningRequestProvenance) throws {
+        notify(accessTo: secret, from: store, by: provenance)
     }
 
 }

Sources/Secretive/Preview Content/PreviewStore.swift

@@ -11,6 +11,7 @@ extension Preview {
         let name: String
         let algorithm = Algorithm.ellipticCurve
         let keySize = 256
+        let requiresAuthentication: Bool = false
         let publicKey = UUID().uuidString.data(using: .utf8)!
 
     }
@@ -35,8 +36,12 @@ extension Preview {
             self.secrets.append(contentsOf: new)
         }
 
-        func sign(data: Data, with secret: Preview.Secret, for provenance: SigningRequestProvenance) throws -> SignedData {
-            return SignedData(data: data, requiredAuthentication: false)
+        func sign(data: Data, with secret: Preview.Secret, for provenance: SigningRequestProvenance) throws -> Data {
+            return data
+        }
+
+        func existingPersistedAuthenticationContext(secret: Preview.Secret) -> PersistedAuthenticationContext? {
+            nil
         }
 
         func persistAuthentication(secret: Preview.Secret, forDuration duration: TimeInterval) throws {

Sources/Secretive/Views/ContentView.swift

@@ -32,6 +32,9 @@ struct ContentView<UpdaterType: UpdaterProtocol, AgentStatusCheckerType: AgentSt
             appPathNotice
             newItem
         }
+        .sheet(isPresented: $runningSetup) {
+            SetupView(visible: $runningSetup, setupComplete: $hasRunSetup)
+        }
     }
 
 }
@@ -65,11 +68,11 @@ extension ContentView {
                         .font(.headline)
                         .foregroundColor(.white)
                 })
-                    .background(color)
-                    .cornerRadius(5)
-                    .popover(item: $selectedUpdate, attachmentAnchor: .point(.bottom), arrowEdge: .bottom) { update in
-                        UpdateDetailView(update: update)
-                    }
+                .background(color)
+                .cornerRadius(5)
+                .popover(item: $selectedUpdate, attachmentAnchor: .point(.bottom), arrowEdge: .bottom) { update in
+                    UpdateDetailView(update: update)
+                }
             )
         }
     }
@@ -85,11 +88,11 @@ extension ContentView {
                 }, label: {
                     Image(systemName: "plus")
                 })
-                    .popover(isPresented: $showingCreation, attachmentAnchor: .point(.bottom), arrowEdge: .bottom) {
-                        if let modifiable = storeList.modifiableStore {
-                            CreateSecretView(store: modifiable, showing: $showingCreation)
-                        }
+                .popover(isPresented: $showingCreation, attachmentAnchor: .point(.bottom), arrowEdge: .bottom) {
+                    if let modifiable = storeList.modifiableStore {
+                        CreateSecretView(store: modifiable, showing: $showingCreation)
                     }
+                }
 
             )
         }
@@ -113,15 +116,12 @@ extension ContentView {
                             .font(.headline)
                             .foregroundColor(.white)
                         })
-                            .background(Color.orange)
-                            .cornerRadius(5)
+                        .background(Color.orange)
+                        .cornerRadius(5)
                     } else {
                         EmptyView()
                     }
                 }
-                    .sheet(isPresented: $runningSetup) {
-                        SetupView(visible: $runningSetup, setupComplete: $hasRunSetup)
-                    }
             )
         }
     }
@@ -142,19 +142,19 @@ extension ContentView {
                     .font(.headline)
                     .foregroundColor(.white)
                 })
-                    .background(Color.orange)
-                    .cornerRadius(5)
-                    .popover(isPresented: $showingAppPathNotice, attachmentAnchor: .point(.bottom), arrowEdge: .bottom) {
-                        VStack {
-                            Image(systemName: "exclamationmark.triangle")
-                                .resizable()
-                                .aspectRatio(contentMode: .fit)
-                                .frame(width: 64)
-                            Text("Secretive needs to be in your Applications folder to work properly. Please move it and relaunch.")
-                                .frame(maxWidth: 300)
-                        }
-                        .padding()
+                .background(Color.orange)
+                .cornerRadius(5)
+                .popover(isPresented: $showingAppPathNotice, attachmentAnchor: .point(.bottom), arrowEdge: .bottom) {
+                    VStack {
+                        Image(systemName: "exclamationmark.triangle")
+                            .resizable()
+                            .aspectRatio(contentMode: .fit)
+                            .frame(width: 64)
+                        Text("Secretive needs to be in your Applications folder to work properly. Please move it and relaunch.")
+                            .frame(maxWidth: 300)
                     }
+                    .padding()
+                }
             )
         }
     }

Sources/Secretive/Views/SecretListItemView.swift

@@ -20,7 +20,15 @@ struct SecretListItemView: View {
         )
 
         return NavigationLink(destination: SecretDetailView(secret: secret), tag: secret.id, selection: $activeSecret) {
-            Text(secret.name)
+            if secret.requiresAuthentication {
+                HStack {
+                    Text(secret.name)
+                    Spacer()
+                    Image(systemName: "lock")
+                }
+            } else {
+                Text(secret.name)
+            }
         }.contextMenu {
             if store is AnySecretStoreModifiable {
                 Button(action: { isRenaming = true }) {