diff --git a/guava/src/test/java/com/fasterxml/jackson/datatype/guava/failing/RangeStringFormatTest.java b/guava/src/test/java/com/fasterxml/jackson/datatype/guava/failing/RangeStringFormatTest.java
new file mode 100644
index 00000000..72ca91db
--- /dev/null
+++ b/guava/src/test/java/com/fasterxml/jackson/datatype/guava/failing/RangeStringFormatTest.java
@@ -0,0 +1,72 @@
+package com.fasterxml.jackson.datatype.guava.failing;
+
+import com.fasterxml.jackson.annotation.JsonFormat;
+import com.fasterxml.jackson.databind.ObjectMapper;
+import com.fasterxml.jackson.datatype.guava.ModuleTestBase;
+import com.fasterxml.jackson.datatype.guava.deser.util.RangeFactory;
+import com.google.common.collect.Range;
+
+import java.time.Duration;
+import java.time.LocalDate;
+
+public class RangeStringFormatTest extends ModuleTestBase
+{
+    private final ObjectMapper MAPPER = mapperWithModule();
+
+    static class Stringified<T extends Comparable<?>>
+    {
+
+        @JsonFormat(shape = JsonFormat.Shape.STRING)
+        public Range<T> r;
+
+        public Stringified() {
+        }
+
+        public Stringified(Range<T> r) {
+            this.r = r;
+        }
+
+        public Range<T> toRange() {
+            return r;
+        }
+    }
+
+    public void testRangeSerializationToString() throws Exception
+    {
+        // Test open range serialization
+        Range<Integer> openRange = RangeFactory.open(1, 10);
+        assertEquals(MAPPER.writeValueAsString(new Stringified<>(openRange)), "{\"r\":\"(1..10)\"}");
+
+        // Test closed range serialization
+        Range<Integer> closedRange = RangeFactory.closed(5, 15);
+        assertEquals(MAPPER.writeValueAsString(new Stringified<>(closedRange)), "{\"r\":\"[5..15]\"}");
+
+        // Test open-closed range serialization
+        Range<Integer> openClosedRange = RangeFactory.openClosed(10, 20);
+        assertEquals(MAPPER.writeValueAsString(new Stringified<>(openClosedRange)), "{\"r\":\"(10..20]\"}");
+
+        // Test closed-open range serialization
+        Range<Integer> closedOpenRange = RangeFactory.closedOpen(25, 30);
+        assertEquals(MAPPER.writeValueAsString(new Stringified<>(closedOpenRange)), "{\"r\":\"[25..30)\"}");
+
+        // Test single point range serialization
+        Range<Integer> singletonRange = RangeFactory.singleton(42);
+        assertEquals(MAPPER.writeValueAsString(new Stringified<>(singletonRange)), "{\"r\":\"[42..42]\"}");
+
+        // Test unbounded range serialization
+        Range<Integer> unboundedRange = RangeFactory.all();
+        assertEquals(MAPPER.writeValueAsString(new Stringified<>(unboundedRange)), "{\"r\":\"(-∞..+∞)\"}");
+
+        // Test open range serialization with Duration
+        Range<Duration> openDurationRange = RangeFactory.open(Duration.ofMinutes(30), Duration.ofMinutes(60));
+        assertEquals(MAPPER.writeValueAsString(new Stringified<>(openDurationRange)), "{\"r\":\"(PT30M..PT1H)\"}");
+
+        // Test closed range serialization with LocalDate
+        Range<LocalDate> closedDateRange = RangeFactory.closed(LocalDate.parse("2023-01-01"), LocalDate.parse("2023-01-31"));
+        assertEquals(MAPPER.writeValueAsString(new Stringified<>(closedDateRange)), "{\"r\":\"[2023-01-01..2023-01-31]\"}");
+
+        // Test open-closed range serialization with String
+        Range<String> openClosedStringRange = RangeFactory.openClosed("abc", "def");
+        assertEquals(MAPPER.writeValueAsString(new Stringified<>(openClosedStringRange)), "{\"r\":\"(abc..def]\"}");
+    }
+}
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