diff --git a/agent/artifact_uploader_test.go b/agent/artifact_uploader_test.go
index f0f88f7e83..255658d1aa 100644
--- a/agent/artifact_uploader_test.go
+++ b/agent/artifact_uploader_test.go
@@ -74,12 +74,29 @@ func TestCollect(t *testing.T) {
 			FileSize:     2038453,
 			Sha1Sum:      "bd4caf2e01e59777744ac1d52deafa01c2cb9bfd",
 		},
+		{
+			Name:         "output.log",
+			Path:         []string{rootWithoutVolume[1:], "test", "fixtures", "artifacts", "nested", "output.log"},
+			AbsolutePath: filepath.Join(root, "test", "fixtures", "artifacts", "nested", "output.log"),
+			GlobPath:     filepath.Join("test", "fixtures", "artifacts", "nested"),
+			FileSize:     14,
+			Sha1Sum:      "1ec2e13e3871a980eaee0f11c6f47ad1d1f97b3e",
+		},
+		{
+			Name:         "logfile.out",
+			Path:         []string{rootWithoutVolume[1:], "test", "fixtures", "artifacts", "nested", "nested0", "logfile.out"},
+			AbsolutePath: filepath.Join(root, "test", "fixtures", "artifacts", "nested", "nested0", "logfile.out"),
+			GlobPath:     filepath.Join("test", "fixtures", "artifacts", "nested"),
+			FileSize:     19,
+			Sha1Sum:      "e30f8100faed6430e6fd617da8ea17100ac97188",
+		},
 	}
 
 	uploader := NewArtifactUploader(logger.Discard, nil, ArtifactUploaderConfig{
-		Paths: fmt.Sprintf("%s;%s",
+		Paths: fmt.Sprintf("%s;%s;%s",
 			filepath.Join("test", "fixtures", "artifacts", "**/*.jpg"),
 			filepath.Join(root, "test", "fixtures", "artifacts", "**/*.gif"),
+			filepath.Join("test", "fixtures", "artifacts", "nested"),
 		),
 	})
 
@@ -109,14 +126,14 @@ func TestCollect(t *testing.T) {
 	if err != nil {
 		t.Fatal(err)
 	}
-	assert.Equal(t, 5, len(artifactsWithoutExperimentEnabled))
+	assert.Equal(t, 7, len(artifactsWithoutExperimentEnabled))
 
 	experiments.Enable(`normalised-upload-paths`)
 	artifactsWithExperimentEnabled, err := uploader.Collect()
 	if err != nil {
 		t.Fatal(err)
 	}
-	assert.Equal(t, 5, len(artifactsWithExperimentEnabled))
+	assert.Equal(t, 7, len(artifactsWithExperimentEnabled))
 
 	// These test cases use filepath.Join, which uses per-OS path separators;
 	// this is the behaviour without normalised-upload-paths.
diff --git a/test/fixtures/artifacts/nested/nested0/logfile.out b/test/fixtures/artifacts/nested/nested0/logfile.out
new file mode 100644
index 0000000000..0364518667
--- /dev/null
+++ b/test/fixtures/artifacts/nested/nested0/logfile.out
@@ -0,0 +1 @@
+logging out to file
\ No newline at end of file
diff --git a/test/fixtures/artifacts/nested/output.log b/test/fixtures/artifacts/nested/output.log
new file mode 100644
index 0000000000..9d0445bbd1
--- /dev/null
+++ b/test/fixtures/artifacts/nested/output.log
@@ -0,0 +1 @@
+logging output
\ No newline at end of file