Harden context handling end to end

Pines/App/PinesAppModel+Presentation.swift

@@ -9,6 +9,7 @@ extension PinesAppModel {
         status: PinesThreadStatus? = nil,
         updatedAt: Date? = nil
     ) -> PinesThreadPreview {
+        let messages = messages.filter { !$0.isContextOnly }
         let lastMessage = previewText(for: messages.last)
         return PinesThreadPreview(
             id: record.id,
@@ -67,6 +68,7 @@ extension PinesAppModel {
         status: PinesThreadStatus? = nil,
         updatedAt: Date = Date()
     ) -> PinesThreadPreview {
+        let messages = messages.filter { !$0.isContextOnly }
         let lastMessage = previewText(for: messages.last)
         let resolvedStatus = existing.status == .archived ? PinesThreadStatus.archived : (status ?? existing.status)
         return PinesThreadPreview(
@@ -95,7 +97,7 @@ extension PinesAppModel {
     }
 
     static func threadTokenCount(_ messages: [ChatMessage]) -> Int {
-        messages.reduce(0) { $0 + max(1, $1.content.split(separator: " ").count) }
+        messages.lazy.filter { !$0.isContextOnly }.reduce(0) { $0 + max(1, $1.content.split(separator: " ").count) }
     }
 
     static func previewText(for message: ChatMessage?) -> String? {

Pines/App/PinesAppModel+Stress.swift

@@ -611,7 +611,7 @@ extension PinesAppModel {
         var lastAssistant: ChatMessage?
         repeat {
             let messages = try await repository.messages(in: conversationID)
-            lastAssistant = messages.last { $0.role == .assistant }
+            lastAssistant = messages.last { $0.role == .assistant && !$0.isContextOnly }
             if lastAssistant?.persistedMessageStatus != .streaming {
                 return lastAssistant
             }

Pines/App/PinesAppModelTypes.swift

@@ -150,14 +150,6 @@ struct PinesThreadPreview: Identifiable, Hashable {
     let updatedLabel: String
     let tokenCount: Int
 
-    var request: ChatRequest {
-        ChatRequest(
-            modelID: modelID,
-            messages: messages,
-            allowsTools: false,
-            vaultContextIDs: []
-        )
-    }
 }
 
 struct PinesProjectPreview: Identifiable, Hashable {

Pines/App/PinesRootView.swift

@@ -754,6 +754,9 @@ private struct CloudContextApprovalSheet: View {
                     LabeledContent("Model", value: request.modelID.rawValue)
                     LabeledContent("Vault documents", value: "\(request.documentIDs.count)")
                     LabeledContent("MCP resources", value: "\(request.mcpResourceIDs.count)")
+                    if let count = request.localTranscriptMessageCount, count > 0 {
+                        LabeledContent("Private transcript rows", value: "\(count)")
+                    }
                     LabeledContent(
                         "Context size",
                         value: ByteCountFormatter.string(
@@ -764,7 +767,7 @@ private struct CloudContextApprovalSheet: View {
                 }
 
                 Section("Privacy") {
-                    Text("Selected local vault and MCP resource context can be sent to this cloud provider for this turn.")
+                    Text("Selected local Vault, MCP resources, and private tool or retrieved context retained from earlier runs can be sent to this cloud provider for this turn.")
                         .font(theme.typography.body)
                         .foregroundStyle(theme.colors.secondaryText)
                 }
@@ -851,6 +854,35 @@ private struct MCPSamplingApprovalSheet: View {
                         .pinesExpressiveScrollHaptics()
                 }
 
+                if let systemPrompt = request.systemPrompt,
+                   !systemPrompt.trimmingCharacters(in: .whitespacesAndNewlines).isEmpty {
+                    Section("Server-provided reference prompt") {
+                        Text(systemPrompt)
+                            .font(theme.typography.code)
+                            .foregroundStyle(theme.colors.secondaryText)
+                            .textSelection(.enabled)
+                        Text("This text is treated as untrusted reference data, never as a Pines system instruction.")
+                            .font(theme.typography.caption)
+                            .foregroundStyle(theme.colors.tertiaryText)
+                    }
+                }
+
+                if !payloadDisclosures.isEmpty {
+                    Section("Request payloads") {
+                        ForEach(Array(payloadDisclosures.enumerated()), id: \.offset) { _, disclosure in
+                            Text(disclosure)
+                                .font(theme.typography.caption)
+                                .foregroundStyle(theme.colors.secondaryText)
+                        }
+                    }
+                }
+
+                Section("Privacy & context") {
+                    Text("Pines does not add ambient chat or Vault history to MCP sampling. It tries a compatible local model first. If local sampling is unavailable and BYOK sampling is enabled for this server, the approved prompt may be sent to your configured cloud provider.")
+                        .font(theme.typography.caption)
+                        .foregroundStyle(theme.colors.secondaryText)
+                }
+
                 if let preferences = request.modelPreferences {
                     Section("Model Preferences") {
                         Text(String(describing: preferences))
@@ -873,6 +905,57 @@ private struct MCPSamplingApprovalSheet: View {
         }
         .pinesDismissKeyboardOnSwipeDown()
     }
+
+    private var payloadDisclosures: [String] {
+        request.messages.enumerated().flatMap { index, message in
+            disclosures(
+                for: message.content,
+                prefix: "Message \(index + 1) (\(message.role.rawValue))"
+            )
+        }
+    }
+
+    private func disclosures(for contents: [MCPMessageContent], prefix: String) -> [String] {
+        disclosures(for: contents, prefix: prefix, depth: 0)
+    }
+
+    private func disclosures(
+        for contents: [MCPMessageContent],
+        prefix: String,
+        depth: Int
+    ) -> [String] {
+        guard depth <= 16 else { return ["\(prefix): nested content limit exceeded"] }
+        return contents.flatMap { content -> [String] in
+            switch content {
+            case let .image(data, mimeType):
+                return ["\(prefix): image \(mimeType), approximately \(estimatedBase64DecodedBytes(data)) bytes"]
+            case let .audio(data, mimeType):
+                return ["\(prefix): audio \(mimeType), approximately \(estimatedBase64DecodedBytes(data)) bytes"]
+            case let .resource(resource):
+                if let blob = resource.blob {
+                    return ["\(prefix): resource \(resource.uri), \(resource.mimeType ?? "unknown type"), approximately \(estimatedBase64DecodedBytes(blob)) bytes"]
+                }
+                return resource.text == nil ? ["\(prefix): resource \(resource.uri)"] : []
+            case let .toolUse(id, name, _):
+                return ["\(prefix): tool use \(id) (\(name))"]
+            case let .toolResult(toolUseID, nested):
+                return disclosures(
+                    for: nested,
+                    prefix: "\(prefix), tool result \(toolUseID)",
+                    depth: depth + 1
+                )
+            case .unknown:
+                return ["\(prefix): unsupported content"]
+            case .text:
+                return []
+            }
+        }
+    }
+
+    private func estimatedBase64DecodedBytes(_ encoded: String) -> Int {
+        let count = encoded.utf8.count
+        return (count / 4) * 3 + min(2, count % 4)
+    }
 }
 
 private struct MCPSamplingResultReviewSheet: View {

Pines/Cloud/BYOKCloudInferenceProvider.swift

@@ -1099,7 +1099,7 @@ struct BYOKCloudInferenceProvider: InferenceProvider {
         }
     }
 
-    private static func anthropicWebSearchToolObject(options: CloudWebSearchOptions?) -> [String: Any] {
+    static func anthropicWebSearchToolObject(options: CloudWebSearchOptions?) -> [String: Any] {
         let resolvedOptions = options ?? CloudWebSearchOptions()
         var tool: [String: Any] = [
             "type": "web_search_20250305",
@@ -1425,6 +1425,9 @@ struct BYOKCloudInferenceProvider: InferenceProvider {
 
     private func openAICompletionTokenLimit(for chatRequest: ChatRequest, usesReasoningParameters: Bool) -> Int {
         let requested = chatRequest.sampling.maxTokens ?? 1024
+        if chatRequest.executionContext == .sampling {
+            return requested
+        }
         guard usesReasoningParameters else { return requested }
         return max(requested, Self.openAIReasoningDefaultMaxCompletionTokens)
     }

Pines/Cloud/PinesManagedCloudService.swift

@@ -64,6 +64,7 @@ struct PinesManagedCloudService: Sendable {
         guard availability.supports(.chat) else {
             throw InferenceError.cloudNotAllowed
         }
+        try Self.validateChatWireContract(request)
         guard let url = endpoint("/v1/chat/stream") else {
             throw InferenceError.invalidRequest("Managed Pro Cloud gateway is not configured.")
         }
@@ -121,9 +122,18 @@ struct PinesManagedCloudService: Sendable {
         guard availability.supports(.tokenPreflight) else {
             throw InferenceError.cloudNotAllowed
         }
+        try Self.validateChatWireContract(request)
         return try await postJSON(ManagedCloudChatRequest(request: request), path: "/v1/tokens/count")
     }
 
+    private static func validateChatWireContract(_ request: ChatRequest) throws {
+        guard request.messages.allSatisfy({ $0.attachments.isEmpty }) else {
+            throw InferenceError.unsupportedCapability(
+                "Managed Pro Cloud chat attachments require an upload wire contract that is not available in this build. Use local or BYOK chat, or the dedicated cloud file-analysis workflow."
+            )
+        }
+    }
+
     func capabilityManifest() async throws -> ManagedCloudCapabilityManifest {
         try await getJSON(path: "/v1/capabilities")
     }

Pines/Persistence/GRDBPinesStore+Mapping.swift

@@ -448,7 +448,8 @@ extension GRDBPinesStore {
             title: row["title"],
             sourceType: row["source_type"],
             updatedAt: Date(timeIntervalSinceReferenceDate: row["updated_at"]),
-            chunkCount: 0
+            chunkCount: 0,
+            projectID: (row["project_id"] as String?).flatMap(UUID.init(uuidString:))
         )
         let chunk = VaultChunk(
             id: row["chunk_id"],