diff --git a/kde/gui/ChatPane.qml b/kde/gui/ChatPane.qml
index 87c6332..6f5e413 100644
--- a/kde/gui/ChatPane.qml
+++ b/kde/gui/ChatPane.qml
@@ -7,12 +7,27 @@ Item {
     id: chatPane
     property bool sidebarVisible: true
     property int maxVisibleBlocks: 80
-    property var pendingBypass: null  // {sessionId, id, cmd, cwd}
-    property bool hasPendingBypass: false
+    // Map of pending bypass requests: id -> {sessionId, agentId, id, cmd, cwd}
+    property var pendingBypasses: ({})
+    property var currentBypass: null  // The one currently shown in the banner
     signal toggleSidebar()
     // Do not opt the chat pane into focus navigation.
     activeFocusOnTab: false
 
+    // Helper to get the first pending bypass for the active agent
+    function updateCurrentBypass() {
+        var activeKey = ollie.activeSessionId + ":" + ollie.activeAgentId
+        for (var id in pendingBypasses) {
+            var req = pendingBypasses[id]
+            var key = req.sessionId + ":" + req.agentId
+            if (key === activeKey) {
+                currentBypass = req
+                return
+            }
+        }
+        currentBypass = null
+    }
+
     // Expose method to set prompt text (for Edit & Resend)
     function setPromptText(text) {
         promptInput.text = text
@@ -175,7 +190,7 @@ Item {
                     color: "#fff3e0"  // amber light
                     border.color: "#ff9800"
                     border.width: 1
-                    visible: chatPane.hasPendingBypass
+                    visible: chatPane.currentBypass !== null
                     z: 100
 
                     ColumnLayout {
@@ -192,7 +207,7 @@ Item {
                         }
 
                         Label {
-                            text: chatPane.pendingBypass ? chatPane.pendingBypass.cmd : ""
+                            text: chatPane.currentBypass ? chatPane.currentBypass.cmd : ""
                             font.family: "monospace"
                             font.pixelSize: theme.fontSize > 0 ? theme.fontSize : 12
                             wrapMode: Text.WrapAnywhere
@@ -201,10 +216,10 @@ Item {
                         }
 
                         Label {
-                            text: chatPane.pendingBypass ? "cwd: " + chatPane.pendingBypass.cwd : ""
+                            text: chatPane.currentBypass ? "cwd: " + chatPane.currentBypass.cwd : ""
                             font.pixelSize: theme.fontSize > 0 ? theme.fontSize - 1 : 10
                             color: "#666"
-                            visible: chatPane.pendingBypass && chatPane.pendingBypass.cwd !== ""
+                            visible: chatPane.currentBypass && chatPane.currentBypass.cwd !== ""
                         }
 
                         RowLayout {
@@ -215,10 +230,8 @@ Item {
                                 text: "Approve"
                                 highlighted: true
                                 onClicked: {
-                                    if (chatPane.pendingBypass) {
-                                        ollie.resolveBypass(chatPane.pendingBypass.sessionId, chatPane.pendingBypass.agentId, chatPane.pendingBypass.id, true)
-                                        chatPane.pendingBypass = null
-                                        chatPane.hasPendingBypass = false
+                                    if (chatPane.currentBypass) {
+                                        ollie.resolveBypass(chatPane.currentBypass.sessionId, chatPane.currentBypass.agentId, chatPane.currentBypass.id, true)
                                     }
                                 }
                             }
@@ -226,10 +239,8 @@ Item {
                             Button {
                                 text: "Deny"
                                 onClicked: {
-                                    if (chatPane.pendingBypass) {
-                                        ollie.resolveBypass(chatPane.pendingBypass.sessionId, chatPane.pendingBypass.agentId, chatPane.pendingBypass.id, false)
-                                        chatPane.pendingBypass = null
-                                        chatPane.hasPendingBypass = false
+                                    if (chatPane.currentBypass) {
+                                        ollie.resolveBypass(chatPane.currentBypass.sessionId, chatPane.currentBypass.agentId, chatPane.currentBypass.id, false)
                                     }
                                 }
                             }
@@ -580,56 +591,46 @@ Connections {
     target: ollie
     function onActiveSessionIdChanged() {
         if (!ollie.activeAgentId) chatPane.loadChat()
-        // Hide bypass banner if it's not for the now-active session
-        if (chatPane.pendingBypass && chatPane.pendingBypass.sessionId !== ollie.activeSessionId) {
-            chatPane.hasPendingBypass = false
-        }
+        // Update current bypass for the new active agent
+        chatPane.updateCurrentBypass()
     }
     function onActiveAgentIdChanged() {
         if (ollie.activeAgentId) chatPane.loadChat()
-        // Hide bypass banner if it's not for the now-active agent
-        if (chatPane.pendingBypass && 
-            (chatPane.pendingBypass.sessionId !== ollie.activeSessionId ||
-             chatPane.pendingBypass.agentId !== ollie.activeAgentId)) {
-            chatPane.hasPendingBypass = false
-        }
+        // Update current bypass for the new active agent
+        chatPane.updateCurrentBypass()
     }
     function onBypassRequested(sessionId, agentId, id, cmd, cwd) {
-        // Show bypass request only for the currently active agent
-        if (sessionId === ollie.activeSessionId && agentId === ollie.activeAgentId) {
-            chatPane.pendingBypass = {
-                sessionId: sessionId,
-                agentId: agentId,
-                id: id,
-                cmd: cmd,
-                cwd: cwd
-            }
-            chatPane.hasPendingBypass = true
+        // Add to pending bypasses map
+        var newMap = chatPane.pendingBypasses
+        newMap[id] = {
+            sessionId: sessionId,
+            agentId: agentId,
+            id: id,
+            cmd: cmd,
+            cwd: cwd
         }
+        chatPane.pendingBypasses = newMap
+        chatPane.updateCurrentBypass()
     }
-    function onBypassResolved(sessionId, agentId) {
-        // Clear bypass banner if it was for this agent (resolved by CLI or another client)
-        if (chatPane.pendingBypass &&
-            chatPane.pendingBypass.sessionId === sessionId &&
-            chatPane.pendingBypass.agentId === agentId) {
-            chatPane.pendingBypass = null
-            chatPane.hasPendingBypass = false
+    function onBypassResolved(sessionId, agentId, requestId) {
+        // Remove the specific resolved request from the map
+        if (chatPane.pendingBypasses[requestId]) {
+            var newMap = chatPane.pendingBypasses
+            delete newMap[requestId]
+            chatPane.pendingBypasses = newMap
+            chatPane.updateCurrentBypass()
         }
     }
 
     // Public functions for keyboard shortcuts
     function approveBypass() {
-        if (chatPane.pendingBypass) {
-            ollie.resolveBypass(chatPane.pendingBypass.sessionId, chatPane.pendingBypass.agentId, chatPane.pendingBypass.id, true)
-            chatPane.pendingBypass = null
-            chatPane.hasPendingBypass = false
+        if (chatPane.currentBypass) {
+            ollie.resolveBypass(chatPane.currentBypass.sessionId, chatPane.currentBypass.agentId, chatPane.currentBypass.id, true)
         }
     }
     function denyBypass() {
-        if (chatPane.pendingBypass) {
-            ollie.resolveBypass(chatPane.pendingBypass.sessionId, chatPane.pendingBypass.agentId, chatPane.pendingBypass.id, false)
-            chatPane.pendingBypass = null
-            chatPane.hasPendingBypass = false
+        if (chatPane.currentBypass) {
+            ollie.resolveBypass(chatPane.currentBypass.sessionId, chatPane.currentBypass.agentId, chatPane.currentBypass.id, false)
         }
     }
 }
diff --git a/kde/gui/ollie9pclient.cpp b/kde/gui/ollie9pclient.cpp
index ac2e622..6558347 100644
--- a/kde/gui/ollie9pclient.cpp
+++ b/kde/gui/ollie9pclient.cpp
@@ -280,7 +280,7 @@ void Ollie9pClient::handleEvent(const QString &eventLine)
                     }
                     emit pendingBypassCountChanged(sidStr, aidStr);
                 }
-                emit bypassResolved(sidStr, aidStr);
+                emit bypassResolved(sidStr, aidStr, id);
             }
         }
     } else {
@@ -895,7 +895,7 @@ bool Ollie9pClient::resolveBypass(const QString &sessionId, const QString &agent
                 m_pendingBypasses.remove(key);
             }
             emit pendingBypassCountChanged(sessionId, agentId);
-            emit bypassResolved(sessionId, agentId);
+            emit bypassResolved(sessionId, agentId, id);
         }
         return true;
     }
diff --git a/kde/gui/ollie9pclient.h b/kde/gui/ollie9pclient.h
index 2ad1590..88021cb 100644
--- a/kde/gui/ollie9pclient.h
+++ b/kde/gui/ollie9pclient.h
@@ -112,7 +112,7 @@ signals:
     void agentStateChanged(const QString &sessionId, const QString &agentId, const QString &state);
     void chatReceived(const QString &text);
     void bypassRequested(const QString &sessionId, const QString &agentId, const QString &id, const QString &cmd, const QString &cwd);
-    void bypassResolved(const QString &sessionId, const QString &agentId);
+    void bypassResolved(const QString &sessionId, const QString &agentId, const QString &requestId);
     void pendingBypassCountChanged(const QString &sessionId, const QString &agentId);
     void procStarted(const QString &sessionId, const QString &agentId, const QString &payload);
     void rootBackendsLoadedChanged();