diff --git a/Wisp/Views/SpriteDetail/Chat/AssistantMessageView.swift b/Wisp/Views/SpriteDetail/Chat/AssistantMessageView.swift
index 2d50360e..991ee4a0 100644
--- a/Wisp/Views/SpriteDetail/Chat/AssistantMessageView.swift
+++ b/Wisp/Views/SpriteDetail/Chat/AssistantMessageView.swift
@@ -85,31 +85,49 @@ private struct AssistantTextBubble: View {
     var onCreateCheckpoint: (() -> Void)? = nil
 
     @State private var showTimestamp = false
+    @State private var isSelectMode = false
 
     var body: some View {
         VStack(alignment: .leading, spacing: 4) {
-            Markdown(text)
-                .markdownTheme(.wisp)
-                .markdownCodeSyntaxHighlighter(WispCodeHighlighter())
-                .textSelection(.enabled)
+            if isSelectMode {
+                SelectableTextView(
+                    text: text,
+                    textColor: .label,
+                    font: .preferredFont(forTextStyle: .body),
+                    onDeselect: { isSelectMode = false }
+                )
                 .padding(.horizontal, 14)
                 .padding(.vertical, 10)
                 .background(Color(.systemGray5), in: RoundedRectangle(cornerRadius: 16))
-                .contextMenu {
-                    Button {
-                        UIPasteboard.general.string = text
-                    } label: {
-                        Label("Copy", systemImage: "doc.on.doc")
-                    }
-                    if canCheckpoint {
+            } else {
+                Markdown(text)
+                    .markdownTheme(.wisp)
+                    .markdownCodeSyntaxHighlighter(WispCodeHighlighter())
+                    .textSelection(.enabled)
+                    .padding(.horizontal, 14)
+                    .padding(.vertical, 10)
+                    .background(Color(.systemGray5), in: RoundedRectangle(cornerRadius: 16))
+                    .contextMenu {
+                        Button {
+                            UIPasteboard.general.string = text
+                        } label: {
+                            Label("Copy", systemImage: "doc.on.doc")
+                        }
                         Button {
-                            onCreateCheckpoint?()
+                            isSelectMode = true
                         } label: {
-                            Label("Create Checkpoint", systemImage: "diamond")
+                            Label("Select", systemImage: "selection.pin.in.out")
+                        }
+                        if canCheckpoint {
+                            Button {
+                                onCreateCheckpoint?()
+                            } label: {
+                                Label("Create Checkpoint", systemImage: "diamond")
+                            }
+                            .disabled(isCheckpointDisabled)
                         }
-                        .disabled(isCheckpointDisabled)
                     }
-                }
+            }
             if showTimestamp {
                 Text(timestamp.chatTimestamp)
                     .font(.caption2)
@@ -119,6 +137,7 @@ private struct AssistantTextBubble: View {
             }
         }
         .onTapGesture {
+            guard !isSelectMode else { return }
             withAnimation(.easeInOut(duration: 0.2)) {
                 showTimestamp.toggle()
             }
diff --git a/Wisp/Views/SpriteDetail/Chat/SelectableTextView.swift b/Wisp/Views/SpriteDetail/Chat/SelectableTextView.swift
new file mode 100644
index 00000000..622d5490
--- /dev/null
+++ b/Wisp/Views/SpriteDetail/Chat/SelectableTextView.swift
@@ -0,0 +1,66 @@
+import SwiftUI
+import UIKit
+
+/// A non-editable UITextView that immediately selects all its text on appearance.
+/// Used for the "Select" context menu action on chat message bubbles.
+struct SelectableTextView: UIViewRepresentable {
+    let text: String
+    let textColor: UIColor
+    let font: UIFont
+    var onDeselect: (() -> Void)?
+
+    func makeCoordinator() -> Coordinator {
+        Coordinator(onDeselect: onDeselect)
+    }
+
+    func makeUIView(context: Context) -> UITextView {
+        let textView = UITextView()
+        textView.isEditable = false
+        textView.isSelectable = true
+        textView.backgroundColor = .clear
+        textView.font = font
+        textView.textColor = textColor
+        textView.textContainerInset = .zero
+        textView.textContainer.lineFragmentPadding = 0
+        textView.isScrollEnabled = false
+        textView.delegate = context.coordinator
+        return textView
+    }
+
+    func updateUIView(_ textView: UITextView, context: Context) {
+        if textView.text != text {
+            textView.text = text
+        }
+        guard !context.coordinator.hasInitiallySelected else { return }
+        DispatchQueue.main.async {
+            textView.selectAll(nil)
+            context.coordinator.hasInitiallySelected = true
+        }
+    }
+
+    class Coordinator: NSObject, UITextViewDelegate {
+        var onDeselect: (() -> Void)?
+        var hasInitiallySelected = false
+
+        init(onDeselect: (() -> Void)?) {
+            self.onDeselect = onDeselect
+        }
+
+        func textViewDidChangeSelection(_ textView: UITextView) {
+            guard hasInitiallySelected, textView.selectedRange.length == 0 else { return }
+            onDeselect?()
+        }
+    }
+}
+
+#Preview {
+    SelectableTextView(
+        text: "Can you add a README to this project?",
+        textColor: .white,
+        font: .preferredFont(forTextStyle: .body)
+    )
+    .padding(.horizontal, 14)
+    .padding(.vertical, 10)
+    .background(.blue, in: RoundedRectangle(cornerRadius: 16))
+    .padding()
+}
diff --git a/Wisp/Views/SpriteDetail/Chat/UserBubbleView.swift b/Wisp/Views/SpriteDetail/Chat/UserBubbleView.swift
index 7e8e5572..e422f01e 100644
--- a/Wisp/Views/SpriteDetail/Chat/UserBubbleView.swift
+++ b/Wisp/Views/SpriteDetail/Chat/UserBubbleView.swift
@@ -3,6 +3,7 @@ import SwiftUI
 struct UserBubbleView: View {
     let message: ChatMessage
     @State private var showTimestamp = false
+    @State private var isSelectMode = false
 
     private func linkedText(_ text: String) -> AttributedString {
         var attributed = AttributedString(text)
@@ -24,19 +25,31 @@ struct UserBubbleView: View {
         HStack {
             Spacer(minLength: 60)
             VStack(alignment: .trailing, spacing: 4) {
-                ForEach(message.content) { content in
-                    if case .text(let text) = content {
-                        Text(linkedText(text))
-                            .padding(.horizontal, 14)
-                            .padding(.vertical, 10)
-                            .background(.blue, in: RoundedRectangle(cornerRadius: 16))
-                            .foregroundStyle(.white)
-                            .tint(.white)
-                            .onTapGesture {
-                                withAnimation(.easeInOut(duration: 0.2)) {
-                                    showTimestamp.toggle()
+                if isSelectMode {
+                    SelectableTextView(
+                        text: message.textContent,
+                        textColor: .white,
+                        font: .preferredFont(forTextStyle: .body),
+                        onDeselect: { isSelectMode = false }
+                    )
+                    .padding(.horizontal, 14)
+                    .padding(.vertical, 10)
+                    .background(.blue, in: RoundedRectangle(cornerRadius: 16))
+                } else {
+                    ForEach(message.content) { content in
+                        if case .text(let text) = content {
+                            Text(linkedText(text))
+                                .padding(.horizontal, 14)
+                                .padding(.vertical, 10)
+                                .background(.blue, in: RoundedRectangle(cornerRadius: 16))
+                                .foregroundStyle(.white)
+                                .tint(.white)
+                                .onTapGesture {
+                                    withAnimation(.easeInOut(duration: 0.2)) {
+                                        showTimestamp.toggle()
+                                    }
                                 }
-                            }
+                        }
                     }
                 }
                 if showTimestamp {
@@ -47,10 +60,17 @@ struct UserBubbleView: View {
                 }
             }
             .contextMenu {
-                Button {
-                    UIPasteboard.general.string = message.textContent
-                } label: {
-                    Label("Copy", systemImage: "doc.on.doc")
+                if !isSelectMode {
+                    Button {
+                        UIPasteboard.general.string = message.textContent
+                    } label: {
+                        Label("Copy", systemImage: "doc.on.doc")
+                    }
+                    Button {
+                        isSelectMode = true
+                    } label: {
+                        Label("Select", systemImage: "selection.pin.in.out")
+                    }
                 }
             }
         }