diff --git a/pkg/sentry/fsimpl/gofer/dentry_impl.go b/pkg/sentry/fsimpl/gofer/dentry_impl.go
index 8bace5dce..1d5c3c02d 100644
--- a/pkg/sentry/fsimpl/gofer/dentry_impl.go
+++ b/pkg/sentry/fsimpl/gofer/dentry_impl.go
@@ -15,6 +15,8 @@
 package gofer
 
 import (
+	"fmt"
+
 	"golang.org/x/sys/unix"
 	"gvisor.dev/gvisor/pkg/abi/linux"
 	"gvisor.dev/gvisor/pkg/atomicbitops"
@@ -511,7 +513,7 @@ func (d *dentry) statfs(ctx context.Context) (linux.Statfs, error) {
 func (fs *filesystem) restoreRoot(ctx context.Context, opts *vfs.CompleteRestoreOptions) error {
 	rootInode, rootHostFD, err := fs.initClientAndGetRoot(ctx)
 	if err != nil {
-		return err
+		return fmt.Errorf("failed to initialize client and get root: %w", err)
 	}
 
 	// The root is always non-synthetic.
@@ -536,14 +538,14 @@ func (d *dentry) restoreFile(ctx context.Context, opts *vfs.CompleteRestoreOptio
 		inode, err := controlFD.Walk(ctx, d.name)
 		if err != nil {
 			if !dt.isDir() || !dt.forMountpoint {
-				return err
+				return fmt.Errorf("failed to walk %q of type %x: %w", genericDebugPathname(d), dt.fileType(), err)
 			}
 
 			// Recreate directories that were created during volume mounting, since
 			// during restore we don't attempt to remount them.
 			inode, err = controlFD.MkdirAt(ctx, d.name, linux.FileMode(d.mode.Load()), lisafs.UID(d.uid.Load()), lisafs.GID(d.gid.Load()))
 			if err != nil {
-				return err
+				return fmt.Errorf("failed to create mountpoint directory at %q: %w", genericDebugPathname(d), err)
 			}
 		}
 		return dt.restoreFile(ctx, &inode, opts)
@@ -556,13 +558,13 @@ func (d *dentry) restoreFile(ctx context.Context, opts *vfs.CompleteRestoreOptio
 		})
 		if err != nil {
 			if !dt.isDir() || !dt.forMountpoint {
-				return err
+				return fmt.Errorf("failed to walk %q of type %x: %w", genericDebugPathname(d), dt.fileType(), err)
 			}
 
 			// Recreate directories that were created during volume mounting, since
 			// during restore we don't attempt to remount them.
 			if err := unix.Mkdirat(controlFD, d.name, d.mode.Load()); err != nil {
-				return err
+				return fmt.Errorf("failed to create mountpoint directory at %q: %w", genericDebugPathname(d), err)
 			}
 
 			// Try again...
@@ -570,7 +572,7 @@ func (d *dentry) restoreFile(ctx context.Context, opts *vfs.CompleteRestoreOptio
 				return unix.Openat(controlFD, d.name, flags, 0)
 			})
 			if err != nil {
-				return err
+				return fmt.Errorf("failed to open %q: %w", genericDebugPathname(d), err)
 			}
 		}
 		return dt.restoreFile(ctx, childFD, opts)
diff --git a/pkg/sentry/fsimpl/gofer/directfs_dentry.go b/pkg/sentry/fsimpl/gofer/directfs_dentry.go
index 4691f077b..7cc268289 100644
--- a/pkg/sentry/fsimpl/gofer/directfs_dentry.go
+++ b/pkg/sentry/fsimpl/gofer/directfs_dentry.go
@@ -645,13 +645,12 @@ func (d *directfsDentry) statfs() (linux.Statfs, error) {
 
 func (d *directfsDentry) restoreFile(ctx context.Context, controlFD int, opts *vfs.CompleteRestoreOptions) error {
 	if controlFD < 0 {
-		log.Warningf("directfsDentry.restoreFile called with invalid controlFD")
-		return unix.EINVAL
+		return fmt.Errorf("directfsDentry.restoreFile called with invalid controlFD")
 	}
 	var stat unix.Stat_t
 	if err := unix.Fstat(controlFD, &stat); err != nil {
 		_ = unix.Close(controlFD)
-		return err
+		return fmt.Errorf("failed to stat %q: %w", genericDebugPathname(&d.dentry), err)
 	}
 
 	d.controlFD = controlFD
@@ -688,7 +687,7 @@ func (d *directfsDentry) restoreFile(ctx context.Context, controlFD int, opts *v
 
 	if rw, ok := d.fs.savedDentryRW[&d.dentry]; ok {
 		if err := d.ensureSharedHandle(ctx, rw.read, rw.write, false /* trunc */); err != nil {
-			return err
+			return fmt.Errorf("failed to restore file handles (read=%t, write=%t) for %q: %w", rw.read, rw.write, genericDebugPathname(&d.dentry), err)
 		}
 	}
 
diff --git a/pkg/sentry/fsimpl/gofer/lisafs_dentry.go b/pkg/sentry/fsimpl/gofer/lisafs_dentry.go
index 245002e0e..28bf85add 100644
--- a/pkg/sentry/fsimpl/gofer/lisafs_dentry.go
+++ b/pkg/sentry/fsimpl/gofer/lisafs_dentry.go
@@ -568,7 +568,7 @@ func (d *lisafsDentry) restoreFile(ctx context.Context, inode *lisafs.Inode, opt
 
 	if rw, ok := d.fs.savedDentryRW[&d.dentry]; ok {
 		if err := d.ensureSharedHandle(ctx, rw.read, rw.write, false /* trunc */); err != nil {
-			return err
+			return fmt.Errorf("failed to restore file handles (read=%t, write=%t) for %q: %w", rw.read, rw.write, genericDebugPathname(&d.dentry), err)
 		}
 	}
 
diff --git a/pkg/sentry/fsimpl/gofer/save_restore.go b/pkg/sentry/fsimpl/gofer/save_restore.go
index e16e11e7e..459ac65fb 100644
--- a/pkg/sentry/fsimpl/gofer/save_restore.go
+++ b/pkg/sentry/fsimpl/gofer/save_restore.go
@@ -196,7 +196,7 @@ func (fs *filesystem) CompleteRestore(ctx context.Context, opts vfs.CompleteRest
 	fs.inoByKey = make(map[inoKey]uint64)
 
 	if err := fs.restoreRoot(ctx, &opts); err != nil {
-		return err
+		return vfs.PrependErrMsg("failed to restore root", err)
 	}
 
 	// Restore remaining dentries.
@@ -260,7 +260,7 @@ func (fd *specialFileFD) completeRestore(ctx context.Context) error {
 	d := fd.dentry()
 	h, err := d.openHandle(ctx, fd.vfsfd.IsReadable(), fd.vfsfd.IsWritable(), false /* trunc */)
 	if err != nil {
-		return err
+		return fmt.Errorf("failed to open handle for specialFileFD for %q: %w", genericDebugPathname(d), err)
 	}
 	fd.handle = h
 
@@ -268,7 +268,7 @@ func (fd *specialFileFD) completeRestore(ctx context.Context) error {
 	fd.haveQueue = (ftype == linux.S_IFIFO || ftype == linux.S_IFSOCK) && fd.handle.fd >= 0
 	if fd.haveQueue {
 		if err := fdnotifier.AddFD(fd.handle.fd, &fd.queue); err != nil {
-			return err
+			return fmt.Errorf("failed to add FD to fdnotified for %q: %w", genericDebugPathname(d), err)
 		}
 	}
 
diff --git a/pkg/sentry/kernel/kernel.go b/pkg/sentry/kernel/kernel.go
index 549472629..a92915d36 100644
--- a/pkg/sentry/kernel/kernel.go
+++ b/pkg/sentry/kernel/kernel.go
@@ -839,7 +839,7 @@ func (k *Kernel) LoadFrom(ctx context.Context, r, pagesMetadata io.Reader, pages
 		pagesFile = nil // transferred to k.loadMemoryFiles()
 	}
 	if mfLoadErr != nil {
-		return mfLoadErr
+		return fmt.Errorf("failed to load memory files: %w", mfLoadErr)
 	}
 
 	if !saveRestoreNet {
@@ -861,7 +861,7 @@ func (k *Kernel) LoadFrom(ctx context.Context, r, pagesMetadata io.Reader, pages
 	}
 
 	if err := k.vfs.CompleteRestore(ctx, vfsOpts); err != nil {
-		return err
+		return vfs.PrependErrMsg("vfs.CompleteRestore() failed", err)
 	}
 
 	tcpip.AsyncLoading.Wait()
diff --git a/pkg/sentry/pgalloc/save_restore.go b/pkg/sentry/pgalloc/save_restore.go
index 2a12db715..951b86bb8 100644
--- a/pkg/sentry/pgalloc/save_restore.go
+++ b/pkg/sentry/pgalloc/save_restore.go
@@ -291,7 +291,7 @@ func (f *MemoryFile) LoadFrom(ctx context.Context, r io.Reader, opts *LoadOpts)
 	f.chunks.Store(&chunks)
 	log.Infof("MemoryFile(%p): loaded metadata in %s", f, time.Since(timeMetadataStart))
 	if err := f.file.Truncate(int64(len(chunks)) * chunkSize); err != nil {
-		return err
+		return fmt.Errorf("failed to truncate MemoryFile: %w", err)
 	}
 	// Obtain chunk mappings, then madvise them concurrently with loading data.
 	var (
@@ -385,7 +385,7 @@ func (f *MemoryFile) LoadFrom(ctx context.Context, r io.Reader, opts *LoadOpts)
 		// Verify header.
 		length, object, err := state.ReadHeader(&wr)
 		if err != nil {
-			return err
+			return fmt.Errorf("failed to read header: %w", err)
 		}
 		if object {
 			// Not expected.
@@ -419,7 +419,7 @@ func (f *MemoryFile) LoadFrom(ctx context.Context, r io.Reader, opts *LoadOpts)
 				_, ioErr = io.ReadFull(r, s)
 			})
 			if ioErr != nil {
-				return ioErr
+				return fmt.Errorf("failed to read pages: %w", ioErr)
 			}
 		}
 
diff --git a/pkg/sentry/vfs/save_restore.go b/pkg/sentry/vfs/save_restore.go
index 5b61b8e1e..5ceb4c36d 100644
--- a/pkg/sentry/vfs/save_restore.go
+++ b/pkg/sentry/vfs/save_restore.go
@@ -36,6 +36,18 @@ func (e ErrCorruption) Error() string {
 	return "restore failed due to external file system state in corruption: " + e.Err.Error()
 }
 
+// PrependErrMsg prepends the passed prefix to the error while preserving
+// special vfs errors as the outer most error.
+func PrependErrMsg(prefix string, err error) error {
+	switch terr := err.(type) {
+	case ErrCorruption:
+		terr.Err = fmt.Errorf("%s: %w", prefix, terr.Err)
+		return terr
+	default:
+		return fmt.Errorf("%s: %w", prefix, err)
+	}
+}
+
 // FilesystemImplSaveRestoreExtension is an optional extension to
 // FilesystemImpl.
 type FilesystemImplSaveRestoreExtension interface {
@@ -68,7 +80,7 @@ func (vfs *VirtualFilesystem) CompleteRestore(ctx context.Context, opts *Complet
 		if ext, ok := fs.impl.(FilesystemImplSaveRestoreExtension); ok {
 			if err := ext.CompleteRestore(ctx, *opts); err != nil {
 				fs.DecRef(ctx)
-				return err
+				return PrependErrMsg(fmt.Sprintf("failed to complete restore for filesystem type %q", fs.fsType.Name()), err)
 			}
 		}
 		fs.DecRef(ctx)
diff --git a/runsc/boot/loader.go b/runsc/boot/loader.go
index f2fe33d23..74d9101a0 100644
--- a/runsc/boot/loader.go
+++ b/runsc/boot/loader.go
@@ -662,9 +662,7 @@ func New(args Args) (*Loader, error) {
 		enableAutosave(l, args.Conf.TestOnlyAutosaveResume, l.saveFDs)
 	}
 
-	if err := l.kernelInitExtra(); err != nil {
-		return nil, err
-	}
+	l.kernelInitExtra()
 
 	// Create the control server using the provided FD.
 	//
diff --git a/runsc/boot/restore.go b/runsc/boot/restore.go
index 2c77690de..8e0d3da2c 100644
--- a/runsc/boot/restore.go
+++ b/runsc/boot/restore.go
@@ -546,7 +546,7 @@ func (r *restorer) restore(l *Loader) error {
 	err = loadOpts.Load(ctx, l.k, nil, oldInetStack, time.NewCalibratedClocks(), &vfs.CompleteRestoreOptions{}, l.saveRestoreNet)
 	r.pagesFile = nil // transferred to loadOpts.Load()
 	if err != nil {
-		return err
+		return fmt.Errorf("failed to load kernel: %w", err)
 	}
 
 	checkpointVersion := popVersionFromCheckpoint(l.k)
@@ -557,10 +557,10 @@ func (r *restorer) restore(l *Loader) error {
 
 	oldSpecs, err := popContainerSpecsFromCheckpoint(l.k)
 	if err != nil {
-		return err
+		return fmt.Errorf("failed to pop container specs from checkpoint: %w", err)
 	}
 	if err := validateSpecs(oldSpecs, l.containerSpecs); err != nil {
-		return err
+		return fmt.Errorf("failed to validate restore spec: %w", err)
 	}
 
 	// Since we have a new kernel we also must make a new watchdog.
@@ -613,9 +613,7 @@ func (r *restorer) restore(l *Loader) error {
 
 	l.k.RestoreContainerMapping(l.containerIDs)
 
-	if err := l.kernelInitExtra(); err != nil {
-		return err
-	}
+	l.kernelInitExtra()
 
 	// Refresh the control server with the newly created kernel.
 	l.ctrl.refreshHandlers()
@@ -625,7 +623,7 @@ func (r *restorer) restore(l *Loader) error {
 
 	// r.restoreDone() signals and waits for the sandbox to start.
 	if err := r.restoreDone(); err != nil {
-		return err
+		return fmt.Errorf("restorer.restoreDone callback failed: %w", err)
 	}
 
 	r.stateFile.Close()
diff --git a/runsc/boot/restore_impl.go b/runsc/boot/restore_impl.go
index 5be050ecb..b49049ea8 100644
--- a/runsc/boot/restore_impl.go
+++ b/runsc/boot/restore_impl.go
@@ -41,6 +41,4 @@ func newProcInternalData(*specs.Spec) *proc.InternalData {
 	return &proc.InternalData{}
 }
 
-func (l *Loader) kernelInitExtra() error {
-	return nil
-}
+func (l *Loader) kernelInitExtra() {}