diff --git a/go/kbfs/libfuse/file.go b/go/kbfs/libfuse/file.go
index 9a6667c31532..e76286b34f7e 100644
--- a/go/kbfs/libfuse/file.go
+++ b/go/kbfs/libfuse/file.go
@@ -192,6 +192,12 @@ func (f *File) sync(ctx context.Context) error {
 
 // Fsync implements the fs.NodeFsyncer interface for File.
 func (f *File) Fsync(ctx context.Context, req *fuse.FsyncRequest) (err error) {
+	ctx, maybeUnmounting, cancel := wrapCtxWithShorterTimeoutForUnmount(f.folder.fs.log, ctx, int(req.Pid))
+	defer cancel()
+	if maybeUnmounting {
+		f.folder.fs.log.CInfof(ctx, "Fsync: maybeUnmounting=true")
+	}
+
 	ctx = f.folder.fs.config.MaybeStartTrace(
 		ctx, "File.Fsync", f.node.GetBasename().String())
 	defer func() { f.folder.fs.config.MaybeFinishTrace(ctx, err) }()
@@ -199,11 +205,14 @@ func (f *File) Fsync(ctx context.Context, req *fuse.FsyncRequest) (err error) {
 	f.folder.fs.vlog.CLogf(ctx, libkb.VLog1, "File Fsync")
 	defer func() { err = f.folder.processError(ctx, libkbfs.WriteMode, err) }()
 
-	// This fits in situation 1 as described in libkbfs/delayed_cancellation.go
-	err = libcontext.EnableDelayedCancellationWithGracePeriod(
-		ctx, f.folder.fs.config.DelayedCancellationGracePeriod())
-	if err != nil {
-		return err
+	if !maybeUnmounting {
+		// This fits in situation 1 as described in
+		// libkbfs/delayed_cancellation.go
+		err = libcontext.EnableDelayedCancellationWithGracePeriod(
+			ctx, f.folder.fs.config.DelayedCancellationGracePeriod())
+		if err != nil {
+			return err
+		}
 	}
 
 	return f.sync(ctx)
diff --git a/go/kbfs/libfuse/fs.go b/go/kbfs/libfuse/fs.go
index 45107448d13f..5a087ca071d3 100644
--- a/go/kbfs/libfuse/fs.go
+++ b/go/kbfs/libfuse/fs.go
@@ -381,13 +381,14 @@ func (f *FS) Root() (fs.Node, error) {
 	return f.root, nil
 }
 
-// quotaUsageStaleTolerance is the lifespan of stale usage data that libfuse
-// accepts in the Statfs handler. In other words, this causes libkbfs to issue
-// a fresh RPC call if cached usage data is older than 10s.
-const quotaUsageStaleTolerance = 10 * time.Second
-
 // Statfs implements the fs.FSStatfser interface for FS.
 func (f *FS) Statfs(ctx context.Context, req *fuse.StatfsRequest, resp *fuse.StatfsResponse) error {
+	ctx, maybeUnmounting, cancel := wrapCtxWithShorterTimeoutForUnmount(f.log, ctx, int(req.Pid))
+	defer cancel()
+	if maybeUnmounting {
+		f.log.CInfof(ctx, "Statfs: maybeUnmounting=true")
+	}
+
 	*resp = fuse.StatfsResponse{
 		Bsize:   fuseBlockSize,
 		Namelen: ^uint32(0),
diff --git a/go/kbfs/libfuse/mounter_non_osx.go b/go/kbfs/libfuse/mounter_non_osx.go
index 00fce1d94f4a..305527cd5a47 100644
--- a/go/kbfs/libfuse/mounter_non_osx.go
+++ b/go/kbfs/libfuse/mounter_non_osx.go
@@ -6,7 +6,12 @@
 
 package libfuse
 
-import "bazil.org/fuse"
+import (
+	"context"
+
+	"bazil.org/fuse"
+	"github.com/keybase/client/go/logger"
+)
 
 func getPlatformSpecificMountOptions(dir string, platformParams PlatformParams) ([]fuse.MountOption, error) {
 	options := []fuse.MountOption{}
@@ -27,3 +32,11 @@ func translatePlatformSpecificError(err error, platformParams PlatformParams) er
 func (m *mounter) reinstallMountDirIfPossible() {
 	// no-op
 }
+
+var noop = func() {}
+
+func wrapCtxWithShorterTimeoutForUnmount(
+	_ logger.Logger, ctx context.Context, _ int) (
+	newCtx context.Context, maybeUnmounting bool, cancel context.CancelFunc) {
+	return ctx, false, noop
+}
diff --git a/go/kbfs/libfuse/mounter_osx.go b/go/kbfs/libfuse/mounter_osx.go
index 25e0ab29fe5d..81aace46d4bd 100644
--- a/go/kbfs/libfuse/mounter_osx.go
+++ b/go/kbfs/libfuse/mounter_osx.go
@@ -7,10 +7,13 @@
 package libfuse
 
 import (
+	"context"
 	"errors"
+	"time"
 
 	"bazil.org/fuse"
 	"github.com/keybase/client/go/install/libnativeinstaller"
+	"github.com/keybase/client/go/logger"
 )
 
 var kbfusePath = fuse.OSXFUSEPaths{
@@ -84,3 +87,39 @@ func (m *mounter) reinstallMountDirIfPossible() {
 	err = libnativeinstaller.InstallMountDir(m.runMode, m.log)
 	m.log.Debug("InstallMountDir: err=%v", err)
 }
+
+// quotaUsageStaleTolerance is the lifespan of stale usage data that libfuse
+// accepts in the Statfs handler. In other words, this causes libkbfs to issue
+// a fresh RPC call if cached usage data is older than 10s.
+const quotaUsageStaleTolerance = 10 * time.Second
+
+const unmountCallTolerance = time.Second
+
+var unmountingExecPaths = map[string]bool{
+	"/usr/sbin/diskutil": true,
+	"/usr/libexec/lsd":   true,
+	"/sbin/umount":       true,
+}
+
+var noop = func() {}
+
+// wrapCtxWithShorterTimeoutForUnmount wraps ctx witha a timeout of
+// unmountCallTolerance if pid is /usr/sbin/diskutil, /usr/libexec/lsd, or
+// /sbin/umount. This is useful for calls that usually happen during unmounting
+// such as Statfs and Fsync. If we block on those calls, `diskutil umount force
+// <mnt>` is blocked as well. So make them timeout after 2s to make unmounting
+// work.
+func wrapCtxWithShorterTimeoutForUnmount(
+	log logger.Logger, ctx context.Context, pid int) (
+	newCtx context.Context, maybeUnmounting bool, cancel context.CancelFunc) {
+	p, err := pidPath(pid)
+	if err != nil {
+		return ctx, false, noop
+	}
+	if unmountingExecPaths[p] {
+		log.CDebugf(ctx, "wrapping context with timeout for %s", p)
+		newCtx, cancel = context.WithTimeout(ctx, unmountCallTolerance)
+		return newCtx, true, cancel
+	}
+	return ctx, false, noop
+}
diff --git a/go/kbfs/libfuse/pidpath_darwin.go b/go/kbfs/libfuse/pidpath_darwin.go
new file mode 100644
index 000000000000..5fca3047de6c
--- /dev/null
+++ b/go/kbfs/libfuse/pidpath_darwin.go
@@ -0,0 +1,41 @@
+// Copyright 2021 Keybase Inc. All rights reserved.
+// Use of this source code is governed by a BSD
+// license that can be found in the LICENSE file.
+//
+// +build darwin
+
+package libfuse
+
+// #include <libproc.h>
+// #include <stdlib.h>
+// #include <errno.h>
+import "C"
+
+import (
+	"errors"
+	"strconv"
+	"unsafe"
+)
+
+// pidPath returns the exec path for process pid. Adapted from
+// https://ops.tips/blog/macos-pid-absolute-path-and-procfs-exploration/
+func pidPath(pid int) (path string, err error) {
+	const bufSize = C.PROC_PIDPATHINFO_MAXSIZE
+	buf := C.CString(string(make([]byte, bufSize)))
+	defer C.free(unsafe.Pointer(buf))
+
+	ret, err := C.proc_pidpath(C.int(pid), unsafe.Pointer(buf), bufSize)
+	if err != nil {
+		return "", err
+	}
+	if ret < 0 {
+		return "", errors.New(
+			"error calling proc_pidpath. exit code: " + strconv.Itoa(int(ret)))
+	}
+	if ret == 0 {
+		return "", errors.New("proc_pidpath returned empty buffer")
+	}
+
+	path = C.GoString(buf)
+	return
+}
diff --git a/go/kbfs/libfuse/pidpath_others.go b/go/kbfs/libfuse/pidpath_others.go
new file mode 100644
index 000000000000..0dc96c69040b
--- /dev/null
+++ b/go/kbfs/libfuse/pidpath_others.go
@@ -0,0 +1,15 @@
+// Copyright 2021 Keybase Inc. All rights reserved.
+// Use of this source code is governed by a BSD
+// license that can be found in the LICENSE file.
+//
+// +build !darwin
+
+package libfuse
+
+import "github.com/pkg/errors"
+
+var notImplementedErr = errors.New("unimplemented")
+
+func pidPath(_ int) (path string, err error) {
+	return "", notImplementedErr
+}
diff --git a/go/mounter/mounter_non_osx.go b/go/mounter/mounter_non_osx.go
index fe48ebb89277..77f37e17d22d 100644
--- a/go/mounter/mounter_non_osx.go
+++ b/go/mounter/mounter_non_osx.go
@@ -5,7 +5,9 @@
 
 package mounter
 
-import "fmt"
+import (
+	"fmt"
+)
 
 // IsMounted returns true if directory is mounted (by kbfuse)
 func IsMounted(dir string, log Log) (bool, error) {