diff --git a/testutils/src/main/java/com/google/android/exoplayer2/testutil/truth/SpannedSubject.java b/testutils/src/main/java/com/google/android/exoplayer2/testutil/truth/SpannedSubject.java
index 1751502ac4..db1c984635 100644
--- a/testutils/src/main/java/com/google/android/exoplayer2/testutil/truth/SpannedSubject.java
+++ b/testutils/src/main/java/com/google/android/exoplayer2/testutil/truth/SpannedSubject.java
@@ -157,18 +157,16 @@ public final class SpannedSubject extends Subject {
       return ALREADY_FAILED_WITH_FLAGS;
     }
 
-    if (styles.size() == 1 && styles.contains(Typeface.BOLD_ITALIC)
-        || styles.size() == 2
-            && styles.contains(Typeface.BOLD)
-            && styles.contains(Typeface.ITALIC)) {
+    if (styles.contains(Typeface.BOLD_ITALIC)
+        || (styles.contains(Typeface.BOLD) && styles.contains(Typeface.ITALIC))) {
       return check("StyleSpan (start=%s,end=%s)", start, end).about(spanFlags()).that(allFlags);
     }
     failWithoutActual(
         simpleFact(
             String.format("No matching StyleSpans found between start=%s,end=%s", start, end)),
         fact("in text", actual.toString()),
-        fact("expected either styles", Collections.singletonList(Typeface.BOLD_ITALIC)),
-        fact("or styles", Arrays.asList(Typeface.BOLD, Typeface.ITALIC)),
+        fact("expected to contain either", Collections.singletonList(Typeface.BOLD_ITALIC)),
+        fact("or both", Arrays.asList(Typeface.BOLD, Typeface.ITALIC)),
         fact("but found styles", styles));
     return ALREADY_FAILED_WITH_FLAGS;
   }
diff --git a/testutils/src/test/java/com/google/android/exoplayer2/testutil/truth/SpannedSubjectTest.java b/testutils/src/test/java/com/google/android/exoplayer2/testutil/truth/SpannedSubjectTest.java
index 32ce419c19..33a67f1c64 100644
--- a/testutils/src/test/java/com/google/android/exoplayer2/testutil/truth/SpannedSubjectTest.java
+++ b/testutils/src/test/java/com/google/android/exoplayer2/testutil/truth/SpannedSubjectTest.java
@@ -151,6 +151,21 @@ public class SpannedSubjectTest {
         .withFlags(Spanned.SPAN_INCLUSIVE_EXCLUSIVE);
   }
 
+  @Test
+  // If the span is both BOLD and BOLD_ITALIC then the assertion should still succeed.
+  public void boldItalicSpan_withRepeatSpans() {
+    SpannableString spannable = SpannableString.valueOf("test with bold & italic section");
+    int start = "test with ".length();
+    int end = start + "bold & italic".length();
+    spannable.setSpan(new StyleSpan(Typeface.BOLD), start, end, Spanned.SPAN_INCLUSIVE_EXCLUSIVE);
+    spannable.setSpan(
+        new StyleSpan(Typeface.BOLD_ITALIC), start, end, Spanned.SPAN_INCLUSIVE_EXCLUSIVE);
+
+    assertThat(spannable)
+        .hasBoldItalicSpanBetween(start, end)
+        .withFlags(Spanned.SPAN_INCLUSIVE_EXCLUSIVE);
+  }
+
   @Test
   public void boldItalicSpan_onlyItalic() {
     SpannableString spannable = SpannableString.valueOf("test with italic section");