diff --git a/taildrop/resume_test.go b/taildrop/resume_test.go
index 43c5dbc81..d366340eb 100644
--- a/taildrop/resume_test.go
+++ b/taildrop/resume_test.go
@@ -15,7 +15,6 @@ import (
 )
 
 func TestResume(t *testing.T) {
-	t.Skip("currently failing on Windows")
 	oldBlockSize := blockSize
 	defer func() { blockSize = oldBlockSize }()
 	blockSize = 256
@@ -29,11 +28,14 @@ func TestResume(t *testing.T) {
 
 	t.Run("resume-noexist", func(t *testing.T) {
 		r := io.Reader(bytes.NewReader(want))
+
 		next, close, err := m.HashPartialFile("", "foo")
 		must.Do(err)
 		defer close()
 		offset, r, err := ResumeReader(r, next)
 		must.Do(err)
+		must.Do(close()) // Windows wants the file handle to be closed to rename it.
+
 		must.Get(m.PutFile("", "foo", r, offset, -1))
 		got := must.Get(os.ReadFile(must.Get(joinDir(m.opts.Dir, "foo"))))
 		if !bytes.Equal(got, want) {
@@ -43,25 +45,30 @@ func TestResume(t *testing.T) {
 
 	t.Run("resume-retry", func(t *testing.T) {
 		rn := rand.New(rand.NewSource(0))
-		for {
+		for i := 0; true; i++ {
 			r := io.Reader(bytes.NewReader(want))
-			next, close, err := m.HashPartialFile("", "foo")
+
+			next, close, err := m.HashPartialFile("", "bar")
 			must.Do(err)
 			defer close()
 			offset, r, err := ResumeReader(r, next)
 			must.Do(err)
+			must.Do(close()) // Windows wants the file handle to be closed to rename it.
+
 			numWant := rn.Int63n(min(int64(len(want))-offset, 1000) + 1)
 			if offset < int64(len(want)) {
 				r = io.MultiReader(io.LimitReader(r, numWant), iotest.ErrReader(io.ErrClosedPipe))
 			}
-			if _, err := m.PutFile("", "foo", r, offset, -1); err == nil {
+			if _, err := m.PutFile("", "bar", r, offset, -1); err == nil {
 				break
 			}
+			if i > 1000 {
+				t.Fatalf("too many iterations to complete the test")
+			}
 		}
-		got := must.Get(os.ReadFile(must.Get(joinDir(m.opts.Dir, "foo"))))
+		got := must.Get(os.ReadFile(must.Get(joinDir(m.opts.Dir, "bar"))))
 		if !bytes.Equal(got, want) {
 			t.Errorf("content mismatches")
 		}
 	})
-
 }