diff --git a/cmd/olliesrv/internal/fs/spec.go b/cmd/olliesrv/internal/fs/spec.go
index 33beb3f..c044b60 100644
--- a/cmd/olliesrv/internal/fs/spec.go
+++ b/cmd/olliesrv/internal/fs/spec.go
@@ -474,13 +474,13 @@ func buildSessionChildren(
 			}, s.GoalSignal),
 		),
 		virtfs.FileNode("bypass", 0666,
-			virtfs.Doc("Bypass request handling. Read: pending request JSON or empty. Write: 'id approve' or 'id deny'."),
+			virtfs.Doc("Bypass request handling. Read: pending requests JSON array. Write: 'id approve' or 'id deny'."),
 			virtfs.Read(func() ([]byte, error) {
-				req := s.BypassPending()
-				if req == nil {
-					return nil, nil
+				reqs := s.BypassPending()
+				if len(reqs) == 0 {
+					return []byte("[]\n"), nil
 				}
-				data, err := json.Marshal(req)
+				data, err := json.Marshal(reqs)
 				if err != nil {
 					return nil, err
 				}
diff --git a/cmd/olliesrv/internal/session/session.go b/cmd/olliesrv/internal/session/session.go
index e89df5d..df7d0fe 100644
--- a/cmd/olliesrv/internal/session/session.go
+++ b/cmd/olliesrv/internal/session/session.go
@@ -63,9 +63,9 @@ type Session struct {
 	modelsCache   string
 	modelsCacheAt time.Time
 
-	// Bypass request tracking
+	// Bypass request tracking (multiple concurrent requests supported)
 	bypassMu       sync.RWMutex
-	bypassPending  *protocol.BypassRequest
+	bypassPending  map[string]*protocol.BypassRequest // keyed by request ID
 	bypassDialFn   func() *toolclient.ToolsrvConn
 	bypassSignalCh chan struct{}
 }
@@ -252,7 +252,10 @@ func (s *Session) GoalSignal() <-chan struct{} {
 // SetBypassPending stores a pending bypass request and publishes an event.
 func (s *Session) SetBypassPending(req *protocol.BypassRequest, dialFn func() *toolclient.ToolsrvConn) {
 	s.bypassMu.Lock()
-	s.bypassPending = req
+	if s.bypassPending == nil {
+		s.bypassPending = make(map[string]*protocol.BypassRequest)
+	}
+	s.bypassPending[req.ID] = req
 	s.bypassDialFn = dialFn
 	if s.bypassSignalCh != nil {
 		close(s.bypassSignalCh)
@@ -270,24 +273,38 @@ func (s *Session) SetBypassPending(req *protocol.BypassRequest, dialFn func() *t
 	PublishEvent("session."+s.ID+".agent."+agentID+".bypass.request", req.ID+"\t"+cmd+"\t"+req.Cwd)
 }
 
-// BypassPending returns the current pending bypass request, or nil if none.
-func (s *Session) BypassPending() *protocol.BypassRequest {
+// BypassPending returns all pending bypass requests.
+func (s *Session) BypassPending() []*protocol.BypassRequest {
 	s.bypassMu.RLock()
 	defer s.bypassMu.RUnlock()
-	return s.bypassPending
+	out := make([]*protocol.BypassRequest, 0, len(s.bypassPending))
+	for _, req := range s.bypassPending {
+		out = append(out, req)
+	}
+	return out
+}
+
+// BypassPendingByID returns a specific pending request by ID.
+func (s *Session) BypassPendingByID(id string) *protocol.BypassRequest {
+	s.bypassMu.RLock()
+	defer s.bypassMu.RUnlock()
+	return s.bypassPending[id]
 }
 
 // ResolveBypass resolves a pending bypass request and clears it.
 func (s *Session) ResolveBypass(id string, approved bool) error {
 	s.bypassMu.Lock()
-	req := s.bypassPending
+	req, ok := s.bypassPending[id]
 	dialFn := s.bypassDialFn
-	if req == nil || req.ID != id {
+	if !ok {
 		s.bypassMu.Unlock()
 		return fmt.Errorf("no pending bypass with id %s", id)
 	}
-	s.bypassPending = nil
-	s.bypassDialFn = nil
+	delete(s.bypassPending, id)
+	// Only clear dialFn if no more pending requests
+	if len(s.bypassPending) == 0 {
+		s.bypassDialFn = nil
+	}
 	if s.bypassSignalCh != nil {
 		close(s.bypassSignalCh)
 	}