diff --git a/integration/integration_test.go b/integration/integration_test.go
index d3cdbf66d6159..818a8e2b3c05c 100644
--- a/integration/integration_test.go
+++ b/integration/integration_test.go
@@ -97,6 +97,7 @@ import (
 	rsession "github.com/gravitational/teleport/lib/session"
 	"github.com/gravitational/teleport/lib/srv/alpnproxy/common"
 	"github.com/gravitational/teleport/lib/sshutils"
+	telesftp "github.com/gravitational/teleport/lib/sshutils/sftp"
 	"github.com/gravitational/teleport/lib/sshutils/x11"
 	"github.com/gravitational/teleport/lib/tlsca"
 	"github.com/gravitational/teleport/lib/utils"
@@ -190,6 +191,7 @@ func TestIntegrations(t *testing.T) {
 	t.Run("DifferentPinnedIP", suite.bind(testDifferentPinnedIP))
 	t.Run("JoinOverReverseTunnelOnly", suite.bind(testJoinOverReverseTunnelOnly))
 	t.Run("SFTP", suite.bind(testSFTP))
+	t.Run("ModeratedSFTP", suite.bind(testModeratedSFTP))
 	t.Run("EscapeSequenceTriggers", suite.bind(testEscapeSequenceTriggers))
 	t.Run("AuthLocalNodeControlStream", suite.bind(testAuthLocalNodeControlStream))
 	t.Run("AgentlessConnection", suite.bind(testAgentlessConnection))
@@ -7934,6 +7936,332 @@ func getRemoteAddrString(sshClientString string) string {
 	return fmt.Sprintf("%s:%s", parts[0], parts[1])
 }
 
+func isNilOrEOFErr(t *testing.T, err error) {
+	t.Helper()
+
+	if err != nil {
+		require.ErrorIs(t, err, io.EOF)
+	}
+}
+
+func testModeratedSFTP(t *testing.T, suite *integrationTestSuite) {
+	modules.SetTestModules(t, &modules.TestModules{
+		TestBuildType: modules.BuildEnterprise,
+	})
+
+	// Create Teleport instance
+	instance := suite.newTeleport(t, nil, true)
+	t.Cleanup(func() {
+		instance.StopAll()
+	})
+
+	ctx := context.Background()
+	authServer := instance.Process.GetAuthServer()
+
+	// Create peer and moderator users and roles
+	username := suite.Me.Username
+	peerUsername := username + "-peer"
+	sshAccessRole, err := types.NewRole("ssh-access", types.RoleSpecV6{
+		Allow: types.RoleConditions{
+			Logins: []string{username},
+			NodeLabels: types.Labels{
+				types.Wildcard: []string{types.Wildcard},
+			},
+		},
+	})
+	require.NoError(t, err)
+	err = authServer.CreateRole(ctx, sshAccessRole)
+	require.NoError(t, err)
+
+	peerRole, err := types.NewRole("peer", types.RoleSpecV6{
+		Allow: types.RoleConditions{
+			RequireSessionJoin: []*types.SessionRequirePolicy{
+				{
+					Name:   "Requires oversight",
+					Filter: `equals("true", "true")`,
+					Kinds: []string{
+						string(types.SSHSessionKind),
+					},
+					Count: 1,
+					Modes: []string{
+						string(types.SessionModeratorMode),
+					},
+					OnLeave: string(types.OnSessionLeaveTerminate),
+				},
+			},
+		},
+	})
+	require.NoError(t, err)
+	err = authServer.CreateRole(ctx, peerRole)
+	require.NoError(t, err)
+
+	peerUser, err := types.NewUser(peerUsername)
+	require.NoError(t, err)
+	peerUser.SetLogins([]string{username})
+	peerUser.SetRoles([]string{sshAccessRole.GetName(), peerRole.GetName()})
+	err = authServer.CreateUser(ctx, peerUser)
+	require.NoError(t, err)
+
+	modUsername := username + "-moderator"
+	modRole, err := types.NewRole("moderator", types.RoleSpecV6{
+		Allow: types.RoleConditions{
+			JoinSessions: []*types.SessionJoinPolicy{{
+				Name:  "Session moderator",
+				Roles: []string{peerRole.GetName()},
+				Kinds: []string{string(types.SSHSessionKind)},
+				Modes: []string{string(types.SessionModeratorMode), string(types.SessionObserverMode)},
+			}},
+		},
+	})
+	require.NoError(t, err)
+	err = authServer.CreateRole(ctx, modRole)
+	require.NoError(t, err)
+
+	moderatorUser, err := types.NewUser(modUsername)
+	require.NoError(t, err)
+	moderatorUser.SetLogins([]string{username})
+	moderatorUser.SetRoles([]string{sshAccessRole.GetName(), modRole.GetName()})
+	err = authServer.CreateUser(ctx, moderatorUser)
+	require.NoError(t, err)
+
+	waitForNodesToRegister(t, instance, helpers.Site)
+
+	// Start a shell so a moderated session is created
+	peerClient, err := instance.NewClient(helpers.ClientConfig{
+		TeleportUser: peerUsername,
+		Login:        username,
+		Cluster:      helpers.Site,
+		Host:         Host,
+	})
+	require.NoError(t, err)
+
+	peerClusterClient, err := peerClient.ConnectToCluster(ctx)
+	require.NoError(t, err)
+	t.Cleanup(func() {
+		require.NoError(t, peerClusterClient.Close())
+	})
+
+	nodeDetails := client.NodeDetails{
+		Addr:      instance.Config.SSH.Addr.Addr,
+		Namespace: peerClient.Namespace,
+		Cluster:   helpers.Site,
+	}
+	peerNodeClient, err := peerClient.ConnectToNode(
+		ctx,
+		peerClusterClient,
+		nodeDetails,
+		username,
+	)
+	require.NoError(t, err)
+	t.Cleanup(func() {
+		require.NoError(t, peerNodeClient.Close())
+	})
+
+	peerSSH := peerNodeClient.Client
+	peerSess, err := peerSSH.NewSession(ctx)
+	require.NoError(t, err)
+	t.Cleanup(func() {
+		require.NoError(t, peerSess.Close())
+	})
+
+	peerTerm := NewTerminal(250)
+	peerSess.Stdin = peerTerm
+	peerSess.Stdout = peerTerm
+	peerSess.Stderr = peerTerm
+	err = peerSess.Shell(ctx)
+	require.NoError(t, err)
+
+	var sessTracker types.SessionTracker
+	require.EventuallyWithT(t, func(t *assert.CollectT) {
+		trackers, err := peerClusterClient.AuthClient.GetActiveSessionTrackers(ctx)
+		assert.NoError(t, err)
+		if assert.Len(t, trackers, 1) {
+			sessTracker = trackers[0]
+		}
+	}, 5*time.Second, 100*time.Millisecond)
+
+	// Join the waiting session so it is approved
+	modTC, err := instance.NewClient(helpers.ClientConfig{
+		TeleportUser: modUsername,
+		Login:        username,
+		Cluster:      helpers.Site,
+		Host:         Host,
+	})
+	require.NoError(t, err)
+
+	modClusterClient, err := modTC.ConnectToCluster(ctx)
+	require.NoError(t, err)
+	t.Cleanup(func() {
+		require.NoError(t, modClusterClient.Close())
+	})
+
+	conn, details, err := modClusterClient.ProxyClient.DialHost(ctx, nodeDetails.Addr, nodeDetails.Cluster, modTC.LocalAgent().ExtendedAgent)
+	require.NoError(t, err)
+	sshConfig := modClusterClient.ProxyClient.SSHConfig(username)
+	modSSHConn, modSSHChans, modSSHReqs, err := tracessh.NewClientConn(ctx, conn, nodeDetails.ProxyFormat(), sshConfig)
+	require.NoError(t, err)
+
+	// We pass an empty channel which we close right away to ssh.NewClient
+	// because the client need to handle requests itself.
+	emptyCh := make(chan *ssh.Request)
+	close(emptyCh)
+	modNodeCli := client.NodeClient{
+		Client:          tracessh.NewClient(modSSHConn, modSSHChans, emptyCh),
+		Namespace:       nodeDetails.Namespace,
+		TC:              modTC,
+		Tracer:          modTC.Tracer,
+		FIPSEnabled:     details.FIPS,
+		ProxyPublicAddr: modTC.WebProxyAddr,
+	}
+
+	modSess, err := modNodeCli.Client.NewSession(ctx)
+	require.NoError(t, err)
+	err = modSess.Setenv(ctx, sshutils.SessionEnvVar, sessTracker.GetSessionID())
+	require.NoError(t, err)
+	err = modSess.Setenv(ctx, teleport.EnvSSHJoinMode, string(types.SessionModeratorMode))
+	require.NoError(t, err)
+
+	modTerm := NewTerminal(250)
+	modSess.Stdin = modTerm
+	modSess.Stdout = modTerm
+	modSess.Stderr = modTerm
+	err = modSess.Shell(ctx)
+	require.NoError(t, err)
+
+	// Create and approve a file download request
+	tempDir := t.TempDir()
+	reqFile := filepath.Join(tempDir, "req-file")
+	err = os.WriteFile(reqFile, []byte("contents"), 0o666)
+	require.NoError(t, err)
+
+	err = peerSess.RequestFileTransfer(ctx, tracessh.FileTransferReq{
+		Download: true,
+		Location: reqFile,
+	})
+	require.NoError(t, err)
+
+	sshReq := <-modSSHReqs
+	var joinEvent apievents.SessionJoin
+	err = json.Unmarshal(sshReq.Payload, &joinEvent)
+	require.NoError(t, err)
+
+	sshReq = <-modSSHReqs
+	var fileReq apievents.FileTransferRequestEvent
+	err = json.Unmarshal(sshReq.Payload, &fileReq)
+	require.NoError(t, err)
+
+	err = modSess.ApproveFileTransferRequest(ctx, fileReq.RequestID)
+	require.NoError(t, err)
+
+	// Ignore file transfer request approve event
+	<-modSSHReqs
+
+	// Test that only operations needed to complete the download
+	// are allowed
+	transferSess, err := peerSSH.NewSession(ctx)
+	require.NoError(t, err)
+	t.Cleanup(func() {
+		isNilOrEOFErr(t, transferSess.Close())
+	})
+
+	err = transferSess.Setenv(ctx, string(telesftp.ModeratedSessionID), sessTracker.GetSessionID())
+	require.NoError(t, err)
+
+	err = transferSess.RequestSubsystem(ctx, teleport.SFTPSubsystem)
+	require.NoError(t, err)
+	w, err := transferSess.StdinPipe()
+	require.NoError(t, err)
+	r, err := transferSess.StdoutPipe()
+	require.NoError(t, err)
+	sftpClient, err := sftp.NewClientPipe(r, w)
+	require.NoError(t, err)
+
+	// A file not in the request shouldn't be allowed
+	_, err = sftpClient.Open(filepath.Join(tempDir, "bad-file"))
+	require.ErrorContains(t, err, `method get is not allowed`)
+	// Since this is a download no files should be allowed to be written to
+	_, err = sftpClient.OpenFile(filepath.Join(tempDir, reqFile), os.O_WRONLY)
+	require.ErrorContains(t, err, `method put is not allowed`)
+	// Only stats and reads should be allowed
+	err = sftpClient.Mkdir(filepath.Join(tempDir, "new-dir"))
+	require.ErrorContains(t, err, `method mkdir is not allowed`)
+	// Since this is a download no files should be allowed to have
+	// their permissions changed
+	err = sftpClient.Chmod(reqFile, 0o777)
+	require.ErrorContains(t, err, `method setstat is not allowed`)
+
+	// Only necessary operations should be allowed
+	_, err = sftpClient.Stat(reqFile)
+	require.NoError(t, err)
+	_, err = sftpClient.Lstat(reqFile)
+	require.NoError(t, err)
+	rf, err := sftpClient.Open(reqFile)
+	require.NoError(t, err)
+	require.NoError(t, rf.Close())
+
+	require.NoError(t, sftpClient.Close())
+
+	// Create and approve a file upload request
+	err = peerSess.RequestFileTransfer(ctx, tracessh.FileTransferReq{
+		Download: false,
+		Filename: "upload-file",
+		Location: reqFile,
+	})
+	require.NoError(t, err)
+
+	sshReq = <-modSSHReqs
+	err = json.Unmarshal(sshReq.Payload, &fileReq)
+	require.NoError(t, err)
+
+	err = modSess.ApproveFileTransferRequest(ctx, fileReq.RequestID)
+	require.NoError(t, err)
+
+	// Ignore file transfer request approve event
+	<-modSSHReqs
+
+	isNilOrEOFErr(t, transferSess.Close())
+	transferSess, err = peerSSH.NewSession(ctx)
+	require.NoError(t, err)
+	t.Cleanup(func() {
+		require.NoError(t, transferSess.Close())
+	})
+
+	err = transferSess.Setenv(ctx, string(telesftp.ModeratedSessionID), sessTracker.GetSessionID())
+	require.NoError(t, err)
+
+	// Test that only operations needed to complete the download
+	// are allowed
+	err = transferSess.RequestSubsystem(ctx, teleport.SFTPSubsystem)
+	require.NoError(t, err)
+	w, err = transferSess.StdinPipe()
+	require.NoError(t, err)
+	r, err = transferSess.StdoutPipe()
+	require.NoError(t, err)
+	sftpClient, err = sftp.NewClientPipe(r, w)
+	require.NoError(t, err)
+
+	// A file not in the request shouldn't be allowed
+	_, err = sftpClient.Open(filepath.Join(tempDir, "bad-file"))
+	require.ErrorContains(t, err, `method get is not allowed`)
+	// Since this is an upload no files should be allowed to be read from
+	_, err = sftpClient.OpenFile(filepath.Join(tempDir, reqFile), os.O_RDONLY)
+	require.ErrorContains(t, err, `method get is not allowed`)
+	// Only stats, writes, and chmods should be allowed
+	err = sftpClient.Mkdir(filepath.Join(tempDir, "new-dir"))
+	require.ErrorContains(t, err, `method mkdir is not allowed`)
+
+	// Only necessary operations should be allowed
+	_, err = sftpClient.Stat(reqFile)
+	require.NoError(t, err)
+	_, err = sftpClient.Lstat(reqFile)
+	require.NoError(t, err)
+	err = sftpClient.Chmod(reqFile, 0o777)
+	require.NoError(t, err)
+	wf, err := sftpClient.OpenFile(reqFile, os.O_WRONLY)
+	require.NoError(t, err)
+	require.NoError(t, wf.Close())
+}
+
 func testSFTP(t *testing.T, suite *integrationTestSuite) {
 	// Create Teleport instance.
 	teleport := suite.newTeleport(t, nil, true)
@@ -7971,6 +8299,9 @@ func testSFTP(t *testing.T, suite *integrationTestSuite) {
 		suite.Me.Username,
 	)
 	require.NoError(t, err)
+	t.Cleanup(func() {
+		require.NoError(t, nodeClient.Close())
+	})
 
 	sftpClient, err := sftp.NewClient(nodeClient.Client.Client)
 	require.NoError(t, err)
diff --git a/lib/srv/ctx.go b/lib/srv/ctx.go
index 2790b346142f4..30d387da645b9 100644
--- a/lib/srv/ctx.go
+++ b/lib/srv/ctx.go
@@ -454,6 +454,10 @@ type ServerContext struct {
 
 	// UserCreatedByTeleport is true when the system user was created by Teleport user auto-provision.
 	UserCreatedByTeleport bool
+
+	// approvedFileReq is an approved file transfer request that will only be
+	// set when the session's pending file transfer request is approved.
+	approvedFileReq *FileTransferRequest
 }
 
 // NewServerContext creates a new *ServerContext which is used to pass and
@@ -1371,3 +1375,23 @@ func (c *ServerContext) GetExecRequest() (Exec, error) {
 	}
 	return c.execRequest, nil
 }
+
+func (c *ServerContext) setApprovedFileTransferRequest(req *FileTransferRequest) {
+	c.mu.Lock()
+	c.approvedFileReq = req
+	c.mu.Unlock()
+}
+
+// ConsumeApprovedFileTransferRequest will return the approved file transfer
+// request for this session if there is one present. Note that if an
+// approved request is returned future calls to this method will return
+// nil to prevent an approved request getting reused incorrectly.
+func (c *ServerContext) ConsumeApprovedFileTransferRequest() *FileTransferRequest {
+	c.mu.Lock()
+	defer c.mu.Unlock()
+
+	req := c.approvedFileReq
+	c.approvedFileReq = nil
+
+	return req
+}
diff --git a/lib/srv/regular/sftp.go b/lib/srv/regular/sftp.go
index df61a6f705833..a3d691c9f3362 100644
--- a/lib/srv/regular/sftp.go
+++ b/lib/srv/regular/sftp.go
@@ -19,6 +19,7 @@ package regular
 import (
 	"bufio"
 	"context"
+	"encoding/json"
 	"errors"
 	"io"
 	"os"
@@ -40,18 +41,20 @@ import (
 const copyingGoroutines = 2
 
 type sftpSubsys struct {
-	sftpCmd   *exec.Cmd
-	serverCtx *srv.ServerContext
-	errCh     chan error
-	log       *logrus.Entry
+	log *logrus.Entry
+
+	fileTransferReq *srv.FileTransferRequest
+	sftpCmd         *exec.Cmd
+	serverCtx       *srv.ServerContext
+	errCh           chan error
 }
 
-func newSFTPSubsys() (*sftpSubsys, error) {
-	// TODO: add prometheus collectors?
+func newSFTPSubsys(fileTransferReq *srv.FileTransferRequest) (*sftpSubsys, error) {
 	return &sftpSubsys{
 		log: logrus.WithFields(logrus.Fields{
 			trace.Component: teleport.ComponentSubsystemSFTP,
 		}),
+		fileTransferReq: fileTransferReq,
 	}, nil
 }
 
@@ -113,9 +116,25 @@ func (s *sftpSubsys) Start(ctx context.Context,
 	if err != nil {
 		return trace.Wrap(err)
 	}
-	// TODO: put in cgroup?
 	execRequest.Continue()
 
+	// Send the file transfer request if applicable. The SFTP process
+	// expects the file transfer request data will end with a null byte,
+	// so if there is no request to send just send a null byte so the
+	// SFTP process can detect that no request was sent.
+	encodedReq := []byte{0x0}
+	if s.fileTransferReq != nil {
+		encodedReq, err = json.Marshal(s.fileTransferReq)
+		if err != nil {
+			return trace.Wrap(err)
+		}
+		encodedReq = append(encodedReq, 0x0)
+	}
+	_, err = chReadPipeIn.Write(encodedReq)
+	if err != nil {
+		return trace.Wrap(err)
+	}
+
 	// Copy the SSH channel to and from the anonymous pipes
 	s.errCh = make(chan error, copyingGoroutines)
 	go func() {
diff --git a/lib/srv/regular/sshserver.go b/lib/srv/regular/sshserver.go
index a0decc619e461..d1b1757ac96c0 100644
--- a/lib/srv/regular/sshserver.go
+++ b/lib/srv/regular/sshserver.go
@@ -2216,7 +2216,7 @@ func (s *Server) parseSubsystemRequest(req *ssh.Request, ctx *srv.ServerContext)
 			return nil, trace.Wrap(err)
 		}
 
-		return newSFTPSubsys()
+		return newSFTPSubsys(ctx.ConsumeApprovedFileTransferRequest())
 	default:
 		return nil, trace.BadParameter("unrecognized subsystem: %v", r.Name)
 	}
diff --git a/lib/srv/sess.go b/lib/srv/sess.go
index 0aba96e6fe3be..6a6d9c6a180a9 100644
--- a/lib/srv/sess.go
+++ b/lib/srv/sess.go
@@ -22,6 +22,9 @@ import (
 	"errors"
 	"fmt"
 	"io"
+	"os"
+	"os/user"
+	"path"
 	"path/filepath"
 	"sync"
 	"sync/atomic"
@@ -436,48 +439,54 @@ func (s *SessionRegistry) GetTerminalSize(sessionID string) (*term.Winsize, erro
 }
 
 func (s *SessionRegistry) isApprovedFileTransfer(scx *ServerContext) (bool, error) {
-	s.sessionsMux.Lock()
-	defer s.sessionsMux.Unlock()
-
-	// get the requested location from env vars
-	location, _ := scx.GetEnv(sftp.FileTransferDstPath)
-	if location == "" {
-		return false, nil
-	}
-	// if a sessID and requestID environment variables were not set, return not approved and no error.
-	// This means the file transfer came from a non-moderated session. sessionID will be passed after a
-	// moderated session approval process has completed.
+	// If the TELEPORT_MODERATED_SESSION_ID environment variable was not
+	// set, return not approved and no error. This means the file
+	// transfer came from a non-moderated session. sessionID will be
+	// passed after a moderated session approval process has completed.
 	sessID, _ := scx.GetEnv(string(sftp.ModeratedSessionID))
 	if sessID == "" {
 		return false, nil
 	}
+
 	// fetch session from registry with sessionID
+	s.sessionsMux.Lock()
 	sess := s.sessions[rsession.ID(sessID)]
+	s.sessionsMux.Unlock()
 	if sess == nil {
 		// If they sent a sessionID and it wasn't found, send an actual error
 		return false, trace.NotFound("Session not found")
 	}
 
-	requestID, _ := scx.GetEnv(string(sftp.FileTransferRequestID))
-	if requestID == "" {
-		return false, nil
-	}
-	// find file transfer request in the session by requestID
-	req := sess.fileTransferRequests[requestID]
-	if req == nil {
-		// If they sent a fileTransferRequestID and it wasn't found, send an actual error
-		return false, trace.NotFound("File transfer request not found")
-	}
+	// acquire the session mutex lock so sess.fileTransferReq doesn't get
+	// written while we're reading it
+	sess.mu.Lock()
+	defer sess.mu.Unlock()
 
-	if req.location != location {
-		return false, trace.AccessDenied("requested destination path does not match the current request")
+	if sess.fileTransferReq == nil {
+		return false, trace.NotFound("Session does not have a pending file transfer request")
 	}
+	if sess.fileTransferReq.Requester != scx.Identity.TeleportUser {
+		// to be safe deny and remove the pending request if the user
+		// doesn't match what we expect
+		req := sess.fileTransferReq
+		sess.fileTransferReq = nil
+
+		sess.BroadcastMessage("file transfer request %s denied due to %s attempting to transfer files", req.ID, scx.Identity.TeleportUser)
+		_ = s.NotifyFileTransferRequest(req, FileTransferDenied, scx)
 
-	if req.requester != scx.Identity.TeleportUser {
 		return false, trace.AccessDenied("Teleport user does not match original requester")
 	}
 
-	return sess.checkIfFileTransferApproved(req)
+	approved, err := sess.checkIfFileTransferApproved(sess.fileTransferReq)
+	if err != nil {
+		return false, trace.Wrap(err)
+	}
+	if approved {
+		scx.setApprovedFileTransferRequest(sess.fileTransferReq)
+		sess.fileTransferReq = nil
+	}
+
+	return approved, nil
 }
 
 // FileTransferRequestEvent is an event used to Notify party members during File Transfer Request approval process
@@ -498,7 +507,7 @@ const (
 
 // NotifyFileTransferRequest is called to notify all members of a party that a file transfer request has been created/approved/denied.
 // The notification is a global ssh request and requires the client to update its UI state accordingly.
-func (s *SessionRegistry) NotifyFileTransferRequest(req *fileTransferRequest, res FileTransferRequestEvent, scx *ServerContext) error {
+func (s *SessionRegistry) NotifyFileTransferRequest(req *FileTransferRequest, res FileTransferRequestEvent, scx *ServerContext) error {
 	session := scx.getSession()
 	if session == nil {
 		s.log.Debugf("Unable to notify %s, no session found in context.", res)
@@ -514,11 +523,11 @@ func (s *SessionRegistry) NotifyFileTransferRequest(req *fileTransferRequest, re
 		SessionMetadata: apievents.SessionMetadata{
 			SessionID: string(sid),
 		},
-		RequestID: req.id,
-		Requester: req.requester,
-		Location:  req.location,
-		Filename:  req.filename,
-		Download:  req.download,
+		RequestID: req.ID,
+		Requester: req.Requester,
+		Location:  req.Location,
+		Filename:  req.Filename,
+		Download:  req.Download,
 		Approvers: make([]string, 0),
 	}
 
@@ -661,10 +670,10 @@ type session struct {
 	// participants at the end of a session.
 	participants map[rsession.ID]*party
 
-	// fileTransferRequests is a set of fileTransferRequests that are currently in the approval
-	// process, or already approved and not yet executed during a moderated session. If a request is
-	// denied or, once it's been executed, it should be removed from this map.
-	fileTransferRequests map[string]*fileTransferRequest
+	// fileTransferReq a pending file transfer request for this session.
+	// If the request is denied or approved it should be set to nil to
+	// prevent its reuse.
+	fileTransferReq *FileTransferRequest
 
 	io       *TermManager
 	inWriter io.WriteCloser
@@ -761,7 +770,6 @@ func newSession(ctx context.Context, id rsession.ID, r *SessionRegistry, scx *Se
 		id:                             id,
 		registry:                       r,
 		parties:                        make(map[rsession.ID]*party),
-		fileTransferRequests:           make(map[string]*fileTransferRequest),
 		participants:                   make(map[rsession.ID]*party),
 		login:                          scx.Identity.Login,
 		stopC:                          make(chan struct{}),
@@ -1676,22 +1684,24 @@ func (s *session) checkPresence(ctx context.Context) error {
 	return nil
 }
 
-// fileTransferRequest is a request to upload or download a file from the node.
-type fileTransferRequest struct {
-	id string
-	// requester is the Teleport User that requested the file transfer
-	requester string
-	// download is true if the request is a download, false if its an upload
-	download bool
-	// filename the name of the file to upload.
-	filename string
-	// location of the requested download or where a file will be uploaded
-	location string
+// FileTransferRequest is a request to upload or download a file from a node.
+type FileTransferRequest struct {
+	// ID is a UUID that uniquely identifies a file transfer request
+	// and is unlikely to collide with another file transfer request
+	ID string
+	// Requester is the Teleport User that requested the file transfer
+	Requester string
+	// Download is true if the request is a download, false if its an upload
+	Download bool
+	// Filename is the name of the file to upload.
+	Filename string
+	// Location of the requested download or where a file will be uploaded
+	Location string
 	// approvers is a list of participants of moderator or peer type that have approved the request
 	approvers map[string]*party
 }
 
-func (s *session) checkIfFileTransferApproved(req *fileTransferRequest) (bool, error) {
+func (s *session) checkIfFileTransferApproved(req *FileTransferRequest) (bool, error) {
 	var participants []auth.SessionAccessContext
 
 	for _, party := range req.approvers {
@@ -1715,44 +1725,104 @@ func (s *session) checkIfFileTransferApproved(req *fileTransferRequest) (bool, e
 }
 
 // newFileTransferRequest takes FileTransferParams and creates a new fileTransferRequest struct
-func (s *session) newFileTransferRequest(params *rsession.FileTransferRequestParams) *fileTransferRequest {
-	return &fileTransferRequest{
-		id:        uuid.New().String(),
-		requester: params.Requester,
-		location:  params.Location,
-		filename:  params.Filename,
-		download:  params.Download,
+func (s *session) newFileTransferRequest(params *rsession.FileTransferRequestParams) (*FileTransferRequest, error) {
+	location, err := s.expandFileTransferRequestPath(params.Location)
+	if err != nil {
+		return nil, trace.Wrap(err)
+	}
+
+	req := FileTransferRequest{
+		ID:        uuid.New().String(),
+		Requester: params.Requester,
+		Location:  location,
+		Filename:  params.Filename,
+		Download:  params.Download,
 		approvers: make(map[string]*party),
 	}
+
+	return &req, nil
+}
+
+func (s *session) expandFileTransferRequestPath(p string) (string, error) {
+	expanded := path.Clean(p)
+	dir := path.Dir(expanded)
+
+	var tildePrefixed bool
+	var noBaseDir bool
+	if dir == "~" {
+		tildePrefixed = true
+	} else if dir == "." {
+		noBaseDir = true
+	}
+
+	if tildePrefixed || noBaseDir {
+		localUser, err := user.Lookup(s.login)
+		if err != nil {
+			return "", trace.Wrap(err)
+		}
+
+		exists, err := CheckHomeDir(localUser)
+		if err != nil {
+			return "", trace.Wrap(err)
+		}
+		homeDir := localUser.HomeDir
+		if !exists {
+			homeDir = string(os.PathSeparator)
+		}
+
+		if tildePrefixed {
+			// expand home dir to make an absolute path
+			expanded = path.Join(homeDir, expanded[2:])
+		} else {
+			// if no directories are specified SFTP will assume the file
+			// to be in the user's home dir
+			expanded = path.Join(homeDir, expanded)
+		}
+	}
+
+	return expanded, nil
 }
 
 // addFileTransferRequest will create a new file transfer request and add it to the current session's fileTransferRequests map
 // and broadcast the appropriate string to the session.
-func (s *session) addFileTransferRequest(params *rsession.FileTransferRequestParams, scx *ServerContext) *fileTransferRequest {
+func (s *session) addFileTransferRequest(params *rsession.FileTransferRequestParams, scx *ServerContext) error {
 	s.mu.Lock()
 	defer s.mu.Unlock()
 
-	req := s.newFileTransferRequest(params)
-	s.fileTransferRequests[req.id] = req
+	if s.fileTransferReq != nil {
+		return trace.AlreadyExists("a file transfer request already exists for this session")
+	}
+	if !params.Download && params.Filename == "" {
+		return trace.BadParameter("no source file is set for the upload")
+	}
+
+	req, err := s.newFileTransferRequest(params)
+	if err != nil {
+		return trace.Wrap(err)
+	}
+	s.fileTransferReq = req
+
 	if params.Download {
 		s.BroadcastMessage("User %s would like to download: %s", params.Requester, params.Location)
 	} else {
 		s.BroadcastMessage("User %s would like to upload %s to: %s", params.Requester, params.Filename, params.Location)
 	}
+	err = s.registry.NotifyFileTransferRequest(s.fileTransferReq, FileTransferUpdate, scx)
 
-	s.registry.NotifyFileTransferRequest(req, FileTransferUpdate, scx)
-	return req
+	return trace.Wrap(err)
 }
 
 // approveFileTransferRequest will add the approver to the approvers map of a file transfer request and notify the members
 // of the session if the updated approvers map would fulfill the moderated policy.
-func (s *session) approveFileTransferRequest(params *rsession.FileTransferDecisionParams, scx *ServerContext) (*fileTransferRequest, error) {
+func (s *session) approveFileTransferRequest(params *rsession.FileTransferDecisionParams, scx *ServerContext) error {
 	s.mu.Lock()
 	defer s.mu.Unlock()
 
-	fileTransferReq := s.fileTransferRequests[params.RequestID]
-	if fileTransferReq == nil {
-		return nil, trace.NotFound("File Transfer Request %s not found", params.RequestID)
+	if s.fileTransferReq == nil {
+		return trace.NotFound("File Transfer Request %s not found", params.RequestID)
+	}
+	if s.fileTransferReq.ID != params.RequestID {
+		return trace.BadParameter("current file transfer request is not %s", params.RequestID)
 	}
 
 	var approver *party
@@ -1762,16 +1832,16 @@ func (s *session) approveFileTransferRequest(params *rsession.FileTransferDecisi
 		}
 	}
 	if approver == nil {
-		return nil, trace.AccessDenied("cannot approve file transfer requests if not in the current moderated session")
+		return trace.AccessDenied("cannot approve file transfer requests if not in the current moderated session")
 	}
 
-	fileTransferReq.approvers[approver.user] = approver
-	s.BroadcastMessage("%s approved file transfer request %s", scx.Identity.TeleportUser, fileTransferReq.id)
+	s.fileTransferReq.approvers[approver.user] = approver
+	s.BroadcastMessage("%s approved file transfer request %s", scx.Identity.TeleportUser, s.fileTransferReq.ID)
 
 	// check if policy is fulfilled
-	approved, err := s.checkIfFileTransferApproved(fileTransferReq)
+	approved, err := s.checkIfFileTransferApproved(s.fileTransferReq)
 	if err != nil {
-		return nil, trace.Wrap(err)
+		return trace.Wrap(err)
 	}
 
 	var eventType FileTransferRequestEvent
@@ -1780,22 +1850,25 @@ func (s *session) approveFileTransferRequest(params *rsession.FileTransferDecisi
 	} else {
 		eventType = FileTransferUpdate
 	}
+	err = s.registry.NotifyFileTransferRequest(s.fileTransferReq, eventType, scx)
 
-	s.registry.NotifyFileTransferRequest(fileTransferReq, eventType, scx)
-
-	return fileTransferReq, nil
+	return trace.Wrap(err)
 }
 
 // denyFileTransferRequest will deny a file transfer request and remove it from the current session's file transfer requests map.
 // A file transfer request does not persist after deny, so there is no "denied" state. Deny in this case is synonymous with delete
 // with the addition of checking for a valid denier.
-func (s *session) denyFileTransferRequest(params *rsession.FileTransferDecisionParams, scx *ServerContext) (*fileTransferRequest, error) {
+func (s *session) denyFileTransferRequest(params *rsession.FileTransferDecisionParams, scx *ServerContext) error {
 	s.mu.Lock()
 	defer s.mu.Unlock()
-	fileTransferReq := s.fileTransferRequests[params.RequestID]
-	if fileTransferReq == nil {
-		return nil, trace.NotFound("file transfer request %s not found", params.RequestID)
+
+	if s.fileTransferReq == nil {
+		return trace.NotFound("file transfer request %s not found", params.RequestID)
+	}
+	if s.fileTransferReq.ID != params.RequestID {
+		return trace.BadParameter("current file transfer request is not %s", params.RequestID)
 	}
+
 	var denier *party
 	for _, p := range s.parties {
 		if p.ctx.ID() == scx.ID() {
@@ -1803,15 +1876,16 @@ func (s *session) denyFileTransferRequest(params *rsession.FileTransferDecisionP
 		}
 	}
 	if denier == nil {
-		return nil, trace.AccessDenied("cannot deny file transfer requests if not in the current moderated session")
+		return trace.AccessDenied("cannot deny file transfer requests if not in the current moderated session")
 	}
 
-	delete(s.fileTransferRequests, fileTransferReq.id)
+	req := s.fileTransferReq
+	s.fileTransferReq = nil
 
-	s.BroadcastMessage("%s denied file transfer request %s", scx.Identity.TeleportUser, fileTransferReq.id)
-	s.registry.NotifyFileTransferRequest(fileTransferReq, FileTransferDenied, scx)
+	s.BroadcastMessage("%s denied file transfer request %s", scx.Identity.TeleportUser, req.ID)
+	err := s.registry.NotifyFileTransferRequest(req, FileTransferDenied, scx)
 
-	return fileTransferReq, nil
+	return trace.Wrap(err)
 }
 
 func (s *session) checkIfStart() (bool, auth.PolicyOptions, error) {
diff --git a/lib/srv/sess_test.go b/lib/srv/sess_test.go
index 627abdfd07a52..c7c4bf01dec4f 100644
--- a/lib/srv/sess_test.go
+++ b/lib/srv/sess_test.go
@@ -139,32 +139,26 @@ func TestIsApprovedFileTransfer(t *testing.T) {
 		name           string
 		expectedResult bool
 		expectedError  string
-		req            *fileTransferRequest
+		req            *FileTransferRequest
 		reqID          string
 		location       string
 	}{
 
 		{
-			name:           "no file request found with supplied ID",
+			name:           "no pending file request",
 			expectedResult: false,
-			expectedError:  "",
+			expectedError:  "Session does not have a pending file transfer request",
 			reqID:          "",
 			req:            nil,
 		},
-		{
-			name:           "no file request found with supplied ID",
-			expectedResult: false,
-			expectedError:  "File transfer request not found",
-			reqID:          "111",
-			req:            nil,
-		},
 		{
 			name:           "current requester does not match original requester",
 			expectedResult: false,
 			expectedError:  "Teleport user does not match original requester",
 			reqID:          "123",
-			req: &fileTransferRequest{
-				requester: "michael",
+			req: &FileTransferRequest{
+				ID:        "123",
+				Requester: "michael",
 				approvers: make(map[string]*party),
 			},
 		},
@@ -174,10 +168,11 @@ func TestIsApprovedFileTransfer(t *testing.T) {
 			expectedError:  "requested destination path does not match the current request",
 			reqID:          "123",
 			location:       "~/Downloads",
-			req: &fileTransferRequest{
-				requester: "michael",
+			req: &FileTransferRequest{
+				ID:        "123",
+				Requester: "teleportUser",
 				approvers: make(map[string]*party),
-				location:  "~/badlocation",
+				Location:  "~/badlocation",
 			},
 		},
 		{
@@ -186,10 +181,11 @@ func TestIsApprovedFileTransfer(t *testing.T) {
 			expectedError:  "",
 			reqID:          "123",
 			location:       "~/Downloads",
-			req: &fileTransferRequest{
-				requester: "teleportUser",
+			req: &FileTransferRequest{
+				ID:        "123",
+				Requester: "teleportUser",
 				approvers: approvers,
-				location:  "~/Downloads",
+				Location:  "~/Downloads",
 			},
 		},
 	}
@@ -199,16 +195,12 @@ func TestIsApprovedFileTransfer(t *testing.T) {
 			// create and add a session to the registry
 			sess, _ := testOpenSession(t, reg, accessRoleSet)
 
-			// create a fileTransferRequest. can be nil
-			sess.fileTransferRequests = map[string]*fileTransferRequest{
-				"123": tt.req,
-			}
+			// create a FileTransferRequest. can be nil
+			sess.fileTransferReq = tt.req
 
 			// new exec request context
 			scx := newTestServerContext(t, reg.Srv, accessRoleSet)
 			scx.SetEnv(string(sftp.ModeratedSessionID), sess.ID())
-			scx.SetEnv(string(sftp.FileTransferRequestID), tt.reqID)
-			scx.SetEnv(sftp.FileTransferDstPath, tt.location)
 			result, err := reg.isApprovedFileTransfer(scx)
 			if err != nil {
 				require.Equal(t, tt.expectedError, err.Error())
diff --git a/lib/srv/termhandlers.go b/lib/srv/termhandlers.go
index 597eebafd82b2..e051d8171b1da 100644
--- a/lib/srv/termhandlers.go
+++ b/lib/srv/termhandlers.go
@@ -146,12 +146,10 @@ func (t *TermHandlers) HandleFileTransferDecision(ctx context.Context, ch ssh.Ch
 	}
 
 	if params.Approved {
-		_, err := session.approveFileTransferRequest(params, scx)
-		return trace.Wrap(err)
+		return trace.Wrap(session.approveFileTransferRequest(params, scx))
 	}
 
-	_, err = session.denyFileTransferRequest(params, scx)
-	return trace.Wrap(err)
+	return trace.Wrap(session.denyFileTransferRequest(params, scx))
 }
 
 // HandleFileTransferRequest handles requests of type "file-transfer-request" which will
@@ -170,8 +168,7 @@ func (t *TermHandlers) HandleFileTransferRequest(ctx context.Context, ch ssh.Cha
 		return nil
 	}
 
-	session.addFileTransferRequest(params, scx)
-	return nil
+	return trace.Wrap(session.addFileTransferRequest(params, scx))
 }
 
 // HandleWinChange handles requests of type "window-change" which update the
diff --git a/lib/sshutils/sftp/http.go b/lib/sshutils/sftp/http.go
index 11181c727e66c..3f1f71753de34 100644
--- a/lib/sshutils/sftp/http.go
+++ b/lib/sshutils/sftp/http.go
@@ -36,14 +36,6 @@ import (
 type contextKey string
 
 const (
-	// FileTransferDstPath is the dstPath (location) for the requested file transfer. This would be equal
-	// to the file to be downloaded, or location for a file to be uploaded.
-	FileTransferDstPath string = "TELEPORT_FILE_TRANSFER_DST_PATH"
-	// FileTransferRequestID is an optional parameter id of an file transfer request that has gone through
-	// an approval process during a moderated session to allow a file transfer scp command to be executed
-	// used as a value in the file transfer context and env var for exec session
-	FileTransferRequestID contextKey = "TELEPORT_FILE_TRANSFER_REQUEST_ID"
-
 	// ModeratedSessionID is an optional parameter sent during SCP requests to specify which moderated session
 	// to check for valid FileTransferRequests
 	// used as a value in the file transfer context and env var for exec session
diff --git a/lib/sshutils/sftp/sftp.go b/lib/sshutils/sftp/sftp.go
index dc8975f20f758..a43b12e6433e2 100644
--- a/lib/sshutils/sftp/sftp.go
+++ b/lib/sshutils/sftp/sftp.go
@@ -237,17 +237,11 @@ func (c *Config) TransferFiles(ctx context.Context, sshClient *ssh.Client) error
 	}
 	defer s.Close()
 
-	// File transfers in a moderated session require these two variables
-	// to check for approval on the ssh server. If they exist in the
-	// context, set them in our env vars
+	// File transfers in a moderated session require this variable
+	// to check for approval on the ssh server
 	if moderatedSessionID, ok := ctx.Value(ModeratedSessionID).(string); ok {
 		s.Setenv(string(ModeratedSessionID), moderatedSessionID)
 	}
-	if fileTransferRequestID, ok := ctx.Value(FileTransferRequestID).(string); ok {
-		s.Setenv(string(FileTransferRequestID), fileTransferRequestID)
-	}
-	// set dstPath in env var to check against file transfer request location
-	s.Setenv(FileTransferDstPath, c.dstPath)
 
 	pe, err := s.StderrPipe()
 	if err != nil {
diff --git a/lib/web/files.go b/lib/web/files.go
index d2ffc4d92bff3..da43dd0bc5b0e 100644
--- a/lib/web/files.go
+++ b/lib/web/files.go
@@ -139,8 +139,6 @@ func (h *Handler) transferFile(w http.ResponseWriter, r *http.Request, p httprou
 
 	ctx := r.Context()
 	if req.fileTransferRequestID != "" {
-		// These values should never exist independently of each other so we can set them at the same time
-		ctx = context.WithValue(ctx, sftp.FileTransferRequestID, req.fileTransferRequestID)
 		ctx = context.WithValue(ctx, sftp.ModeratedSessionID, req.moderatedSessionID)
 	}
 
diff --git a/tool/teleport/common/sftp.go b/tool/teleport/common/sftp.go
index c14e8dffd6516..fcb09af394a5d 100644
--- a/tool/teleport/common/sftp.go
+++ b/tool/teleport/common/sftp.go
@@ -17,13 +17,17 @@ limitations under the License.
 package common
 
 import (
+	"bufio"
 	"bytes"
+	"encoding/json"
 	"errors"
 	"fmt"
 	"io"
 	"io/fs"
 	"os"
 	"os/user"
+	"path"
+	"strings"
 	"time"
 
 	"github.com/gogo/protobuf/jsonpb"
@@ -36,6 +40,7 @@ import (
 	apievents "github.com/gravitational/teleport/api/types/events"
 	"github.com/gravitational/teleport/lib/defaults"
 	"github.com/gravitational/teleport/lib/events"
+	"github.com/gravitational/teleport/lib/srv"
 	"github.com/gravitational/teleport/lib/utils"
 )
 
@@ -73,17 +78,70 @@ func (c compositeCh) Close() error {
 	return trace.NewAggregate(c.r.Close(), c.w.Close())
 }
 
+type allowedOps struct {
+	write bool
+	path  string
+}
+
 // sftpHandler provides handlers for a SFTP server.
 type sftpHandler struct {
-	logger *log.Entry
-	events chan<- *apievents.SFTP
+	logger  *log.Entry
+	allowed *allowedOps
+	events  chan<- *apievents.SFTP
 }
 
-func newSFTPHandler(logger *log.Entry, events chan<- *apievents.SFTP) *sftpHandler {
+func newSFTPHandler(logger *log.Entry, req *srv.FileTransferRequest, events chan<- *apievents.SFTP) (*sftpHandler, error) {
+	var allowed *allowedOps
+	if req != nil {
+		allowed = &allowedOps{
+			write: !req.Download,
+		}
+		// TODO(capnspacehook): reject relative paths and symlinks
+		// make filepaths consistent by ensuring all separators use backslashes
+		allowed.path = path.Clean(req.Location)
+	}
+
 	return &sftpHandler{
-		logger: logger,
-		events: events,
+		logger:  logger,
+		allowed: allowed,
+		events:  events,
+	}, nil
+}
+
+func newDisallowedErr(req *sftp.Request) error {
+	return fmt.Errorf("method %s is not allowed on %s", strings.ToLower(req.Method), req.Filepath)
+}
+
+// ensureReqIsAllowed returns an error if the SFTP request isn't
+// allowed based on the approved file transfer request for this session.
+func (s *sftpHandler) ensureReqIsAllowed(req *sftp.Request) error {
+	// no specifically allowed operations, all requests are allowed
+	if s.allowed == nil {
+		return nil
 	}
+
+	if s.allowed.path != path.Clean(req.Filepath) {
+		return newDisallowedErr(req)
+	}
+
+	switch req.Method {
+	case methodLstat, methodStat:
+		// these methods are allowed
+	case methodGet:
+		// only allow reads for downloads
+		if s.allowed.write {
+			return newDisallowedErr(req)
+		}
+	case methodPut, methodSetStat:
+		// only allow writes and chmods for uploads
+		if !s.allowed.write {
+			return newDisallowedErr(req)
+		}
+	default:
+		return newDisallowedErr(req)
+	}
+
+	return nil
 }
 
 // OpenFile handles 'open' requests when opening a file for reading
@@ -129,6 +187,10 @@ func (s *sftpHandler) Filewrite(req *sftp.Request) (_ io.WriterAt, retErr error)
 }
 
 func (s *sftpHandler) openFile(req *sftp.Request) (*os.File, error) {
+	if err := s.ensureReqIsAllowed(req); err != nil {
+		return nil, err
+	}
+
 	var flags int
 	pflags := req.Pflags()
 	if pflags.Append {
@@ -172,6 +234,9 @@ func (s *sftpHandler) Filecmd(req *sftp.Request) (retErr error) {
 	if req.Filepath == "" {
 		return os.ErrInvalid
 	}
+	if err := s.ensureReqIsAllowed(req); err != nil {
+		return err
+	}
 
 	switch req.Method {
 	case methodSetStat:
@@ -306,6 +371,9 @@ func (s *sftpHandler) Filelist(req *sftp.Request) (_ sftp.ListerAt, retErr error
 	if req.Filepath == "" {
 		return nil, os.ErrInvalid
 	}
+	if err := s.ensureReqIsAllowed(req); err != nil {
+		return nil, err
+	}
 
 	switch req.Method {
 	case methodList:
@@ -344,6 +412,9 @@ func (s *sftpHandler) Lstat(req *sftp.Request) (sftp.ListerAt, error) {
 	if req.Filepath == "" {
 		return nil, os.ErrInvalid
 	}
+	if err := s.ensureReqIsAllowed(req); err != nil {
+		return nil, err
+	}
 
 	fi, err := os.Lstat(req.Filepath)
 	if err != nil {
@@ -492,7 +563,6 @@ func onSFTP() error {
 		return trace.Wrap(err)
 	}
 	defer chw.Close()
-	ch := compositeCh{chr, chw}
 	auditFile, err := openFD(5, "audit")
 	if err != nil {
 		return trace.Wrap(err)
@@ -501,7 +571,6 @@ func onSFTP() error {
 
 	// Ensure the parent process will receive log messages from us
 	l := utils.NewLogger()
-	l.SetOutput(os.Stderr)
 	logger := l.WithField(trace.Component, teleport.ComponentSubsystemSFTP)
 
 	currentUser, err := user.Current()
@@ -513,8 +582,34 @@ func onSFTP() error {
 		return trace.Wrap(err)
 	}
 
+	// Read the file transfer request for this session if one exists
+	bufferedReader := bufio.NewReader(chr)
+	var encodedReq []byte
+	var fileTransferReq *srv.FileTransferRequest
+	for {
+		b, err := bufferedReader.ReadByte()
+		if err != nil {
+			return trace.Wrap(err)
+		}
+		// the encoded request will end with a null byte
+		if b == 0x0 {
+			break
+		}
+		encodedReq = append(encodedReq, b)
+	}
+	if len(encodedReq) != 0 {
+		fileTransferReq = new(srv.FileTransferRequest)
+		if err := json.Unmarshal(encodedReq, fileTransferReq); err != nil {
+			return trace.Wrap(err)
+		}
+	}
+	ch := compositeCh{io.NopCloser(bufferedReader), chw}
+
 	sftpEvents := make(chan *apievents.SFTP, 1)
-	h := newSFTPHandler(logger, sftpEvents)
+	h, err := newSFTPHandler(logger, fileTransferReq, sftpEvents)
+	if err != nil {
+		return trace.Wrap(err)
+	}
 	handler := sftp.Handlers{
 		FileGet:  h,
 		FilePut:  h,