diff --git a/cmd/olliesrv/internal/bypass/broker.go b/cmd/olliesrv/internal/bypass/broker.go
index 2f133ef..1725ca2 100644
--- a/cmd/olliesrv/internal/bypass/broker.go
+++ b/cmd/olliesrv/internal/bypass/broker.go
@@ -1,6 +1,7 @@
 package bypass
 
 import (
+	"context"
 	"fmt"
 	"sync"
 	"time"
@@ -84,8 +85,14 @@ func (b *Broker) Pending() []*Request {
 }
 
 // NextPending blocks until a bypass request is available and returns it.
-func (b *Broker) NextPending() *Request {
-	return <-b.pendingCh
+// Returns nil if context is cancelled before a request arrives.
+func (b *Broker) NextPending(ctx context.Context) *Request {
+	select {
+	case req := <-b.pendingCh:
+		return req
+	case <-ctx.Done():
+		return nil
+	}
 }
 
 // PendingByID returns a specific pending request.
diff --git a/cmd/olliesrv/internal/fs/spec.go b/cmd/olliesrv/internal/fs/spec.go
index 8387f12..380f82e 100644
--- a/cmd/olliesrv/internal/fs/spec.go
+++ b/cmd/olliesrv/internal/fs/spec.go
@@ -171,13 +171,13 @@ func buildTreeSpec(cfg *Config) virtfs.FsNodeDecl {
 			virtfs.Doc("Bypass broker for sandboxed command approval"),
 			virtfs.FileNode("pending", 0444,
 				virtfs.Doc("Blocks until bypass request; returns JSON {id, cmd, cwd, env}"),
-				virtfs.BlockOnce(func(_ context.Context, _ string) ([]byte, string, error) {
+				virtfs.BlockOnce(func(ctx context.Context, _ string) ([]byte, string, error) {
 					if broker == nil {
 						return nil, "", errNoBypass
 					}
-					req := broker.NextPending()
+					req := broker.NextPending(ctx)
 					if req == nil {
-						return nil, "", fmt.Errorf("no pending request")
+						return nil, "", fmt.Errorf("context cancelled")
 					}
 					data, err := json.Marshal(req)
 					if err != nil {
diff --git a/cmd/toolsrv/internal/bypass/bypass.go b/cmd/toolsrv/internal/bypass/bypass.go
index 9dcc0e3..edba4fc 100644
--- a/cmd/toolsrv/internal/bypass/bypass.go
+++ b/cmd/toolsrv/internal/bypass/bypass.go
@@ -75,8 +75,14 @@ func Submit(ctx context.Context, cmd, cwd string, env map[string]string) (bool,
 
 // NextPending blocks until a request is available and returns it.
 // Used by the 9P pending file to expose requests to the approver.
-func NextPending() *Request {
-	return <-pending
+// Returns nil if context is cancelled before a request arrives.
+func NextPending(ctx context.Context) *Request {
+	select {
+	case req := <-pending:
+		return req
+	case <-ctx.Done():
+		return nil
+	}
 }
 
 // Resolve completes a pending request with the given decision.
diff --git a/cmd/toolsrv/internal/server/server.go b/cmd/toolsrv/internal/server/server.go
index f99c167..f03a275 100644
--- a/cmd/toolsrv/internal/server/server.go
+++ b/cmd/toolsrv/internal/server/server.go
@@ -134,8 +134,11 @@ func Spec(srv *Server) virtfs.FsNodeDecl {
 		virtfs.DirNode("bypass",
 			virtfs.FileNode("pending", 0444,
 				virtfs.Doc("Blocks until bypass request; returns JSON {id, cmd, cwd, env}"),
-				virtfs.BlockOnce(func(_ context.Context, _ string) ([]byte, string, error) {
-					req := bypass.NextPending()
+				virtfs.BlockOnce(func(ctx context.Context, _ string) ([]byte, string, error) {
+					req := bypass.NextPending(ctx)
+					if req == nil {
+						return nil, "", fmt.Errorf("context cancelled")
+					}
 					data, err := json.Marshal(req)
 					if err != nil {
 						return nil, "", err
diff --git a/cmd/toolsrv/p9.go b/cmd/toolsrv/p9.go
index b7c616e..5cf7535 100644
--- a/cmd/toolsrv/p9.go
+++ b/cmd/toolsrv/p9.go
@@ -24,6 +24,7 @@ type fid struct {
 	entry    virtfs.File
 	readBuf  []byte // buffer for read data
 	readDone bool   // true if file has been read
+	waitBase string // base string for blocking/stream reads
 	dirCache []byte
 }
 
@@ -375,7 +376,52 @@ func handleRead(cs *connState, fc *plan9.Fcall, tree *virtfs.Tree) *plan9.Fcall
 		return &plan9.Fcall{Type: plan9.Rread, Tag: fc.Tag, Data: nil}
 	}
 
-	// Buffer read data if not already done
+	// Handle BlockOnce mode: block until content is available, then cache it
+	if f.entry.BlockingReadMode() {
+		// Serve from cache if we already have content (multi-Tread paging)
+		if f.readBuf != nil {
+			if int(fc.Offset) >= len(f.readBuf) {
+				return &plan9.Fcall{Type: plan9.Rread, Tag: fc.Tag, Count: 0}
+			}
+			return readSlice(fc, f.readBuf)
+		}
+		// First Tread: block for content
+		content, nextBase, err := f.entry.BlockingRead(cs.ctx, f.waitBase)
+		if err != nil {
+			return errFcall(fc, err.Error())
+		}
+		if nextBase != "" {
+			cs.mu.Lock()
+			if ff, ok := cs.fids[fc.Fid]; ok {
+				ff.waitBase = nextBase
+			}
+			cs.mu.Unlock()
+		}
+		f.readBuf = content
+		return readSlice(fc, content)
+	}
+
+	// Handle Stream mode: block indefinitely, stream data incrementally
+	if f.entry.StreamMode() {
+		content, nextBase, err := f.entry.BlockingRead(cs.ctx, f.waitBase)
+		if err != nil {
+			return errFcall(fc, err.Error())
+		}
+		if nextBase != "" {
+			cs.mu.Lock()
+			if ff, ok := cs.fids[fc.Fid]; ok {
+				ff.waitBase = nextBase
+			}
+			cs.mu.Unlock()
+		}
+		count := int(fc.Count)
+		if count > len(content) {
+			count = len(content)
+		}
+		return &plan9.Fcall{Type: plan9.Rread, Tag: fc.Tag, Count: uint32(count), Data: content[:count]}
+	}
+
+	// Buffer read data if not already done (normal non-blocking read)
 	if f.readBuf == nil {
 		data, err := f.entry.Read()
 		if err != nil && err != io.EOF {
@@ -399,6 +445,20 @@ func handleRead(cs *connState, fc *plan9.Fcall, tree *virtfs.Tree) *plan9.Fcall
 	return &plan9.Fcall{Type: plan9.Rread, Tag: fc.Tag, Data: f.readBuf[offset:end]}
 }
 
+// readSlice returns a slice of content based on offset/count from fc.
+func readSlice(fc *plan9.Fcall, content []byte) *plan9.Fcall {
+	var data []byte
+	off := int(fc.Offset)
+	if off < len(content) {
+		end := off + int(fc.Count)
+		if end > len(content) {
+			end = len(content)
+		}
+		data = content[off:end]
+	}
+	return &plan9.Fcall{Type: plan9.Rread, Tag: fc.Tag, Count: uint32(len(data)), Data: data}
+}
+
 func handleDirRead(cs *connState, f *fid, fc *plan9.Fcall, tree *virtfs.Tree) *plan9.Fcall {
 	if fc.Offset == 0 || f.dirCache == nil {
 		path := f.path