diff --git a/test/Tests/src/Data/Text_Spec.enso b/test/Tests/src/Data/Text_Spec.enso
index cd02f5b8d14e8..10816a789de6a 100644
--- a/test/Tests/src/Data/Text_Spec.enso
+++ b/test/Tests/src/Data/Text_Spec.enso
@@ -513,6 +513,16 @@ spec =
             long_text . starts_with "EOL.SOL" (Regex_Matcher.new dot_matches_newline=True) . should_be_true
             long_text . starts_with "EOL.SOL" (Regex_Matcher.new dot_matches_newline=False) . should_be_false
 
+            "aaazzz" . starts_with "a|b" Regex_Matcher.new . should_be_true
+            "bbbzzz" . starts_with "a|b" Regex_Matcher.new . should_be_true
+            "zzzaaa" . starts_with "a|b" Regex_Matcher.new . should_be_false
+            "zzzbbb" . starts_with "a|b" Regex_Matcher.new . should_be_false
+            "aaazzz" . starts_with "(a|b){2}" Regex_Matcher.new . should_be_true
+            "bbbzzz" . starts_with "(a|b){2}" Regex_Matcher.new . should_be_true
+            "zzzaaa" . starts_with "(a|b){2}" Regex_Matcher.new . should_be_false
+            "foobar" . starts_with "" Regex_Matcher.new . should_be_true
+            "" . starts_with "" Regex_Matcher.new . should_be_true
+
         Test.specify "should check for ends_with using Unicode normalization" <|
             "Hello".ends_with "lo" . should_be_true
             "Hello".ends_with "LO" . should_be_false
@@ -581,6 +591,16 @@ spec =
             long_text . ends_with "EOL.SOL" (Regex_Matcher.new dot_matches_newline=True) . should_be_true
             long_text . ends_with "EOL.SOL" (Regex_Matcher.new dot_matches_newline=False) . should_be_false
 
+            "zzzaaa" . ends_with "a|b" Regex_Matcher.new . should_be_true
+            "zzzbbb" . ends_with "a|b" Regex_Matcher.new . should_be_true
+            "aaazzz" . ends_with "a|b" Regex_Matcher.new . should_be_false
+            "bbbzzz" . ends_with "a|b" Regex_Matcher.new . should_be_false
+            "zzzaaa" . ends_with "(a|b){2}" Regex_Matcher.new . should_be_true
+            "zzzbbb" . ends_with "(a|b){2}" Regex_Matcher.new . should_be_true
+            "aaazzz" . ends_with "(a|b){2}" Regex_Matcher.new . should_be_false
+            "foobar" . ends_with "" Regex_Matcher.new . should_be_true
+            "" . ends_with "" Regex_Matcher.new . should_be_true
+
     Test.group "Regex matching" <|
         Test.specify "should be possible on text" <|
             match = "My Text: Goes Here".match "^My Text: (.+)$" mode=Regex_Mode.First