diff --git a/pkg/util/contextutil/context.go b/pkg/util/contextutil/context.go
index db7dbb03597c..87a139437153 100644
--- a/pkg/util/contextutil/context.go
+++ b/pkg/util/contextutil/context.go
@@ -79,6 +79,18 @@ func wrap(ctx context.Context, cancel context.CancelFunc) (context.Context, cont
 	}
 }
 
+// ctxWithStacktrace overrides Err to annotate context.DeadlineExceeded and
+// context.Canceled errors with a stacktrace.
+// See: https://github.com/cockroachdb/cockroach/issues/95794
+type ctxWithStacktrace struct {
+	context.Context
+}
+
+// Err implements the context.Context interface.
+func (ctx *ctxWithStacktrace) Err() error {
+	return errors.WithStack(ctx.Context.Err())
+}
+
 // RunWithTimeout runs a function with a timeout, the same way you'd do with
 // context.WithTimeout. It improves the opaque error messages returned by
 // WithTimeout by augmenting them with the op string that is passed in.
@@ -86,6 +98,7 @@ func RunWithTimeout(
 	ctx context.Context, op string, timeout time.Duration, fn func(ctx context.Context) error,
 ) error {
 	ctx, cancel := context.WithTimeout(ctx, timeout)
+	ctx = &ctxWithStacktrace{Context: ctx}
 	defer cancel()
 	start := timeutil.Now()
 	err := fn(ctx)
diff --git a/pkg/util/contextutil/context_test.go b/pkg/util/contextutil/context_test.go
index 35b89803d5b6..dc3f5f8e8cb1 100644
--- a/pkg/util/contextutil/context_test.go
+++ b/pkg/util/contextutil/context_test.go
@@ -12,6 +12,7 @@ package contextutil
 
 import (
 	"context"
+	"fmt"
 	"net"
 	"testing"
 	"time"
@@ -68,6 +69,24 @@ func TestRunWithTimeout(t *testing.T) {
 	}
 }
 
+func testFuncA(ctx context.Context) error {
+	return testFuncB(ctx)
+}
+
+func testFuncB(ctx context.Context) error {
+	<-ctx.Done()
+	return ctx.Err()
+}
+
+func TestRunWithTimeoutCtxWithStacktrace(t *testing.T) {
+	ctx := context.Background()
+	err := RunWithTimeout(ctx, "foo", 1, testFuncA)
+	require.Error(t, err)
+	stacktrace := fmt.Sprintf("%+v", err)
+	require.Contains(t, stacktrace, "testFuncB")
+	require.Contains(t, stacktrace, "testFuncA")
+}
+
 // TestRunWithTimeoutWithoutDeadlineExceeded ensures that when a timeout on the
 // context occurs but the underlying error does not have
 // context.DeadlineExceeded as its Cause (perhaps due to serialization) the