diff --git a/runtime/docker/build.go b/runtime/docker/build.go
index 22d7cff..3daf3d9 100644
--- a/runtime/docker/build.go
+++ b/runtime/docker/build.go
@@ -10,6 +10,7 @@ import (
 	"os"
 	"path/filepath"
 	"strings"
+	"time"
 
 	"github.com/moby/moby/api/types/build"
 	"github.com/moby/moby/client"
@@ -168,6 +169,12 @@ func streamBuildOutput(ctx context.Context, body io.ReadCloser, events chan<- ru
 	}
 }
 
+// tarEpoch is the canonical normalized mtime stamped into every tar
+// header by tarDirectory. Using unix epoch (rather than time.Time{},
+// which clamps to epoch anyway in USTAR) makes intent explicit and
+// avoids any reader special-casing the year-1 sentinel.
+var tarEpoch = time.Unix(0, 0)
+
 // tarDirectory writes the contents of dir (recursively) into w as a
 // non-gzipped tar archive. Symlinks are preserved as tar TypeSymlink
 // entries with their original target text; the daemon-side BuildKit
@@ -217,6 +224,22 @@ func tarDirectory(dir string, w io.Writer) error {
 		if d.IsDir() {
 			hdr.Name = rel + "/"
 		}
+		// Normalize metadata so the tar stream — and therefore
+		// BuildKit's COPY vertex digest — is reproducible across
+		// invocations and machines. Wall-clock mtimes from
+		// os.WriteFile (e.g. useruid's synthesized context) and
+		// host-specific uid/gid would otherwise perturb the digest of
+		// byte-identical content, causing cache misses and forcing
+		// re-extraction of downstream image layers. BuildKit hashes
+		// content for cache purposes, so erasing these fields doesn't
+		// lose information it relies on.
+		hdr.ModTime = tarEpoch
+		hdr.AccessTime = time.Time{}
+		hdr.ChangeTime = time.Time{}
+		hdr.Uid = 0
+		hdr.Gid = 0
+		hdr.Uname = ""
+		hdr.Gname = ""
 
 		if err := tw.WriteHeader(hdr); err != nil {
 			return err
diff --git a/runtime/docker/build_test.go b/runtime/docker/build_test.go
index 3e9f7a2..3b24f41 100644
--- a/runtime/docker/build_test.go
+++ b/runtime/docker/build_test.go
@@ -1,8 +1,14 @@
 package docker
 
 import (
+	"archive/tar"
+	"bytes"
+	"io"
+	"os"
+	"path/filepath"
 	"reflect"
 	"testing"
+	"time"
 )
 
 func TestExtractBaseImages(t *testing.T) {
@@ -92,6 +98,91 @@ FROM alpine:3.20 AS b`,
 	}
 }
 
+// TestTarDirectoryNormalizesMetadata guards against the BuildKit
+// COPY-cache regression caused by wall-clock mtimes in synthesized
+// build contexts (uid-reconcile, etc.) leaking into the tar stream and
+// perturbing the vertex digest of byte-identical content.
+func TestTarDirectoryNormalizesMetadata(t *testing.T) {
+	dir := t.TempDir()
+	if err := os.WriteFile(filepath.Join(dir, "file.txt"), []byte("hello"), 0o644); err != nil {
+		t.Fatalf("write: %v", err)
+	}
+	if err := os.Mkdir(filepath.Join(dir, "sub"), 0o755); err != nil {
+		t.Fatalf("mkdir: %v", err)
+	}
+	if err := os.WriteFile(filepath.Join(dir, "sub", "nested.txt"), []byte("world"), 0o644); err != nil {
+		t.Fatalf("write nested: %v", err)
+	}
+
+	var buf bytes.Buffer
+	if err := tarDirectory(dir, &buf); err != nil {
+		t.Fatalf("tarDirectory: %v", err)
+	}
+
+	tr := tar.NewReader(&buf)
+	entries := 0
+	for {
+		hdr, err := tr.Next()
+		if err == io.EOF {
+			break
+		}
+		if err != nil {
+			t.Fatalf("tar.Next: %v", err)
+		}
+		entries++
+		if !hdr.ModTime.Equal(time.Unix(0, 0)) {
+			t.Errorf("%s: ModTime not epoch: %v", hdr.Name, hdr.ModTime)
+		}
+		if !hdr.AccessTime.IsZero() {
+			t.Errorf("%s: AccessTime not zero: %v", hdr.Name, hdr.AccessTime)
+		}
+		if !hdr.ChangeTime.IsZero() {
+			t.Errorf("%s: ChangeTime not zero: %v", hdr.Name, hdr.ChangeTime)
+		}
+		if hdr.Uid != 0 || hdr.Gid != 0 {
+			t.Errorf("%s: uid/gid not zero: uid=%d gid=%d", hdr.Name, hdr.Uid, hdr.Gid)
+		}
+		if hdr.Uname != "" || hdr.Gname != "" {
+			t.Errorf("%s: uname/gname not empty: uname=%q gname=%q", hdr.Name, hdr.Uname, hdr.Gname)
+		}
+	}
+	if entries == 0 {
+		t.Fatal("no tar entries read")
+	}
+}
+
+// TestTarDirectoryDeterministic asserts that taring the same content
+// twice with diverging wall-clock mtimes produces byte-identical
+// streams — the property BuildKit's COPY cache relies on.
+func TestTarDirectoryDeterministic(t *testing.T) {
+	mkContext := func(t *testing.T, mtime time.Time) string {
+		t.Helper()
+		dir := t.TempDir()
+		p := filepath.Join(dir, "uid-fix.sh")
+		if err := os.WriteFile(p, []byte("#!/bin/sh\nexit 0\n"), 0o755); err != nil {
+			t.Fatalf("write: %v", err)
+		}
+		if err := os.Chtimes(p, mtime, mtime); err != nil {
+			t.Fatalf("chtimes: %v", err)
+		}
+		return dir
+	}
+
+	a := mkContext(t, time.Unix(1_700_000_000, 0))
+	b := mkContext(t, time.Unix(1_800_000_000, 0))
+
+	var bufA, bufB bytes.Buffer
+	if err := tarDirectory(a, &bufA); err != nil {
+		t.Fatalf("tarDirectory a: %v", err)
+	}
+	if err := tarDirectory(b, &bufB); err != nil {
+		t.Fatalf("tarDirectory b: %v", err)
+	}
+	if !bytes.Equal(bufA.Bytes(), bufB.Bytes()) {
+		t.Fatalf("tar streams differ despite identical content (mtime leaked)")
+	}
+}
+
 func TestSubstituteArgs(t *testing.T) {
 	args := map[string]string{"X": "alpine", "Y": "3.20"}
 	cases := []struct {
diff --git a/useruid.go b/useruid.go
index 8610c53..4aeb264 100644
--- a/useruid.go
+++ b/useruid.go
@@ -8,6 +8,7 @@ import (
 	"runtime"
 	"strconv"
 	"syscall"
+	"time"
 
 	"github.com/crunchloop/devcontainer/config"
 	"github.com/crunchloop/devcontainer/events"
@@ -84,11 +85,26 @@ func (e *Engine) reconcileRemoteUserUID(ctx context.Context, cfg *config.Resolve
 	}
 	defer os.RemoveAll(tmp)
 
-	if err := os.WriteFile(filepath.Join(tmp, "uid-fix.sh"), []byte(uidReconcileScript), 0o755); err != nil {
+	// Pin synthesized-context file times to the epoch so the tar
+	// stream is stable across invocations regardless of wall-clock.
+	// runtime/docker/build.go also normalizes tar headers as a
+	// defense-in-depth measure, but keeping the on-disk mtimes
+	// deterministic here means this context's reproducibility is a
+	// local property — independent of any consumer's tar pipeline.
+	epoch := time.Unix(0, 0)
+	uidFix := filepath.Join(tmp, "uid-fix.sh")
+	if err := os.WriteFile(uidFix, []byte(uidReconcileScript), 0o755); err != nil {
+		return "", err
+	}
+	if err := os.Chtimes(uidFix, epoch, epoch); err != nil {
 		return "", err
 	}
 	df := generateUIDDockerfile(finalImage, user, hostUID, hostGID)
-	if err := os.WriteFile(filepath.Join(tmp, "Dockerfile"), []byte(df), 0o644); err != nil {
+	dfPath := filepath.Join(tmp, "Dockerfile")
+	if err := os.WriteFile(dfPath, []byte(df), 0o644); err != nil {
+		return "", err
+	}
+	if err := os.Chtimes(dfPath, epoch, epoch); err != nil {
 		return "", err
 	}
 	opts.bus.Emit(events.BuildStartEvent{Source: events.BuildSourceUIDReconcile, Ref: tag})