diff --git a/src/test/java/com/fasterxml/jackson/databind/deser/jdk/EnumMapDeserializer5165Test.java b/src/test/java/com/fasterxml/jackson/databind/deser/jdk/EnumMapDeserializer5165Test.java
new file mode 100644
index 0000000000..b4e9b03c85
--- /dev/null
+++ b/src/test/java/com/fasterxml/jackson/databind/deser/jdk/EnumMapDeserializer5165Test.java
@@ -0,0 +1,63 @@
+package com.fasterxml.jackson.databind.deser.jdk;
+
+import java.util.EnumMap;
+
+import org.junit.jupiter.api.Test;
+
+import com.fasterxml.jackson.annotation.JsonSetter;
+import com.fasterxml.jackson.annotation.Nulls;
+import com.fasterxml.jackson.core.type.TypeReference;
+import com.fasterxml.jackson.databind.ObjectMapper;
+import com.fasterxml.jackson.databind.exc.InvalidNullException;
+import com.fasterxml.jackson.databind.json.JsonMapper;
+import org.opentest4j.AssertionFailedError;
+
+import static org.junit.jupiter.api.Assertions.assertFalse;
+import static org.junit.jupiter.api.Assertions.assertThrows;
+
+// For [databind#5165]
+public class EnumMapDeserializer5165Test
+{
+    public enum MyEnum {
+        FOO
+    }
+
+    static class Dst {
+        private EnumMap<MyEnum, Integer> map;
+
+        public EnumMap<MyEnum, Integer> getMap() {
+            return map;
+        }
+
+        public void setMap(EnumMap<MyEnum, Integer> map) {
+            this.map = map;
+        }
+    }
+
+    @Test
+    public void nullsFailTest() {
+        ObjectMapper mapper = JsonMapper.builder()
+                .defaultSetterInfo(JsonSetter.Value.forContentNulls(Nulls.FAIL))
+                .build();
+
+        assertThrows(
+                AssertionFailedError.class,
+                () -> assertThrows(
+                        InvalidNullException.class,
+                        () -> mapper.readValue("{\"map\":{\"FOO\":\"\"}}", new TypeReference<Dst>(){})
+                ),
+                "databind#5165 for EnumMapDeserializer is fixed"
+        );
+    }
+
+    @Test
+    public void nullsSkipTest() throws Exception {
+        ObjectMapper mapper = JsonMapper.builder()
+                .defaultSetterInfo(JsonSetter.Value.forContentNulls(Nulls.SKIP))
+                .build();
+
+        Dst dst = mapper.readValue("{\"map\":{\"FOO\":\"\"}}", new TypeReference<Dst>() {});
+
+        assertFalse(dst.getMap().isEmpty(), "databind#5165 for EnumMapDeserializer is fixed");
+    }
+}
diff --git a/src/test/java/com/fasterxml/jackson/databind/deser/jdk/EnumSetDeserializer5165Test.java b/src/test/java/com/fasterxml/jackson/databind/deser/jdk/EnumSetDeserializer5165Test.java
new file mode 100644
index 0000000000..3b7eaf2833
--- /dev/null
+++ b/src/test/java/com/fasterxml/jackson/databind/deser/jdk/EnumSetDeserializer5165Test.java
@@ -0,0 +1,98 @@
+package com.fasterxml.jackson.databind.deser.jdk;
+
+import java.io.IOException;
+import java.util.EnumSet;
+
+import org.junit.jupiter.api.Test;
+
+import com.fasterxml.jackson.annotation.JsonSetter;
+import com.fasterxml.jackson.annotation.Nulls;
+import com.fasterxml.jackson.core.JsonParser;
+import com.fasterxml.jackson.core.type.TypeReference;
+import com.fasterxml.jackson.databind.DeserializationContext;
+import com.fasterxml.jackson.databind.ObjectMapper;
+import com.fasterxml.jackson.databind.deser.std.StdDeserializer;
+import com.fasterxml.jackson.databind.exc.InvalidNullException;
+import com.fasterxml.jackson.databind.json.JsonMapper;
+import com.fasterxml.jackson.databind.module.SimpleModule;
+import org.opentest4j.AssertionFailedError;
+
+import static org.junit.jupiter.api.Assertions.assertFalse;
+import static org.junit.jupiter.api.Assertions.assertThrows;
+
+// For [databind#5165]
+public class EnumSetDeserializer5165Test
+{
+    public enum MyEnum {
+        FOO
+    }
+
+    static class Dst {
+        private EnumSet<MyEnum> set;
+
+        public EnumSet<MyEnum> getSet() {
+            return set;
+        }
+
+        public void setSet(EnumSet<MyEnum> set) {
+            this.set = set;
+        }
+    }
+
+    // Custom deserializer that converts empty strings to null
+    static class EmptyStringToNullDeserializer extends StdDeserializer<MyEnum> {
+        private static final long serialVersionUID = 1L;
+
+        public EmptyStringToNullDeserializer() {
+            super(MyEnum.class);
+        }
+
+        @Override
+        public MyEnum deserialize(JsonParser p, DeserializationContext ctxt) throws IOException {
+            String value = p.getValueAsString();
+            if (value != null && value.isEmpty()) {
+                return null;
+            }
+            return MyEnum.valueOf(value);
+        }
+    }
+
+    private ObjectMapper createMapperWithCustomDeserializer() {
+        SimpleModule module = new SimpleModule();
+        module.addDeserializer(MyEnum.class, new EmptyStringToNullDeserializer());
+
+        return JsonMapper.builder()
+                .addModule(module)
+                .defaultSetterInfo(JsonSetter.Value.forContentNulls(Nulls.FAIL))
+                .build();
+    }
+
+    @Test
+    public void nullsFailTest() {
+        ObjectMapper mapper = createMapperWithCustomDeserializer();
+
+        assertThrows(
+                AssertionFailedError.class,
+                () -> assertThrows(
+                        InvalidNullException.class,
+                        () -> mapper.readValue("{\"set\":[\"\"]}", new TypeReference<Dst>(){})
+                ),
+                "databind#5165 for EnumSetDeserializer is fixed"
+        );
+    }
+
+    @Test
+    public void nullsSkipTest() throws Exception {
+        SimpleModule module = new SimpleModule();
+        module.addDeserializer(MyEnum.class, new EmptyStringToNullDeserializer());
+
+        ObjectMapper mapper = JsonMapper.builder()
+                .addModule(module)
+                .defaultSetterInfo(JsonSetter.Value.forContentNulls(Nulls.SKIP))
+                .build();
+
+        Dst dst = mapper.readValue("{\"set\":[\"FOO\",\"\"]}", new TypeReference<Dst>() {});
+
+        assertFalse(dst.getSet().isEmpty(), "databind#5165 for EnumSetDeserializer is fixed");
+    }
+}
diff --git a/src/test/java/com/fasterxml/jackson/databind/deser/jdk/MapDeserializer5165Test.java b/src/test/java/com/fasterxml/jackson/databind/deser/jdk/MapDeserializer5165Test.java
new file mode 100644
index 0000000000..415804cd8d
--- /dev/null
+++ b/src/test/java/com/fasterxml/jackson/databind/deser/jdk/MapDeserializer5165Test.java
@@ -0,0 +1,59 @@
+package com.fasterxml.jackson.databind.deser.jdk;
+
+import java.util.Map;
+
+import org.junit.jupiter.api.Test;
+
+import com.fasterxml.jackson.annotation.JsonSetter;
+import com.fasterxml.jackson.annotation.Nulls;
+import com.fasterxml.jackson.core.type.TypeReference;
+import com.fasterxml.jackson.databind.ObjectMapper;
+import com.fasterxml.jackson.databind.exc.InvalidNullException;
+import com.fasterxml.jackson.databind.json.JsonMapper;
+import org.opentest4j.AssertionFailedError;
+
+import static org.junit.jupiter.api.Assertions.assertFalse;
+import static org.junit.jupiter.api.Assertions.assertThrows;
+
+// For [databind#5165]
+public class MapDeserializer5165Test
+{
+    static class Dst {
+        private Map<String, Integer> map;
+
+        public Map<String, Integer> getMap() {
+            return map;
+        }
+
+        public void setMap(Map<String, Integer> map) {
+            this.map = map;
+        }
+    }
+
+    @Test
+    public void nullsFailTest() {
+        ObjectMapper mapper = JsonMapper.builder()
+                .defaultSetterInfo(JsonSetter.Value.forContentNulls(Nulls.FAIL))
+                .build();
+
+        assertThrows(
+                AssertionFailedError.class,
+                () -> assertThrows(
+                        InvalidNullException.class,
+                        () -> mapper.readValue("{\"map\":{\"key\":\"\"}}", new TypeReference<Dst>(){})
+                ),
+                "databind#5165 for MapDeserializer is fixed"
+        );
+    }
+
+    @Test
+    public void nullsSkipTest() throws Exception {
+        ObjectMapper mapper = JsonMapper.builder()
+                .defaultSetterInfo(JsonSetter.Value.forContentNulls(Nulls.SKIP))
+                .build();
+
+        Dst dst = mapper.readValue("{\"map\":{\"key\":\"\"}}", new TypeReference<Dst>() {});
+
+        assertFalse(dst.getMap().isEmpty(), "databind#5165 for MapDeserializer is fixed");
+    }
+}
diff --git a/src/test/java/com/fasterxml/jackson/databind/deser/jdk/ObjectArrayDeserializer5165Test.java b/src/test/java/com/fasterxml/jackson/databind/deser/jdk/ObjectArrayDeserializer5165Test.java
new file mode 100644
index 0000000000..c23db14a3d
--- /dev/null
+++ b/src/test/java/com/fasterxml/jackson/databind/deser/jdk/ObjectArrayDeserializer5165Test.java
@@ -0,0 +1,57 @@
+package com.fasterxml.jackson.databind.deser.jdk;
+
+import org.junit.jupiter.api.Test;
+
+import com.fasterxml.jackson.annotation.JsonSetter;
+import com.fasterxml.jackson.annotation.Nulls;
+import com.fasterxml.jackson.core.type.TypeReference;
+import com.fasterxml.jackson.databind.ObjectMapper;
+import com.fasterxml.jackson.databind.exc.InvalidNullException;
+import com.fasterxml.jackson.databind.json.JsonMapper;
+import org.opentest4j.AssertionFailedError;
+
+import static org.junit.jupiter.api.Assertions.assertFalse;
+import static org.junit.jupiter.api.Assertions.assertThrows;
+
+// For [databind#5165]
+public class ObjectArrayDeserializer5165Test
+{
+    static class Dst {
+        private Integer[] array;
+
+        public Integer[] getArray() {
+            return array;
+        }
+
+        public void setArray(Integer[] array) {
+            this.array = array;
+        }
+    }
+
+    @Test
+    public void nullsFailTest() {
+        ObjectMapper mapper = JsonMapper.builder()
+                .defaultSetterInfo(JsonSetter.Value.forContentNulls(Nulls.FAIL))
+                .build();
+
+        assertThrows(
+                AssertionFailedError.class,
+                () -> assertThrows(
+                        InvalidNullException.class,
+                        () -> mapper.readValue("{\"array\":[\"\"]}", new TypeReference<Dst>(){})
+                ),
+                "databind#5165 for ObjectArrayDeserializer is fixed"
+        );
+    }
+
+    @Test
+    public void nullsSkipTest() throws Exception {
+        ObjectMapper mapper = JsonMapper.builder()
+                .defaultSetterInfo(JsonSetter.Value.forContentNulls(Nulls.SKIP))
+                .build();
+
+        Dst dst = mapper.readValue("{\"array\":[\"\"]}", new TypeReference<Dst>() {});
+
+        assertFalse(dst.getArray() == null || dst.getArray().length == 0, "databind#5165 for ObjectArrayDeserializer is fixed");
+    }
+}
diff --git a/src/test/java/com/fasterxml/jackson/databind/deser/jdk/StringArrayDeserializer5165Test.java b/src/test/java/com/fasterxml/jackson/databind/deser/jdk/StringArrayDeserializer5165Test.java
new file mode 100644
index 0000000000..8bbdf220a0
--- /dev/null
+++ b/src/test/java/com/fasterxml/jackson/databind/deser/jdk/StringArrayDeserializer5165Test.java
@@ -0,0 +1,93 @@
+package com.fasterxml.jackson.databind.deser.jdk;
+
+import java.io.IOException;
+
+import org.junit.jupiter.api.Test;
+
+import com.fasterxml.jackson.annotation.JsonSetter;
+import com.fasterxml.jackson.annotation.Nulls;
+import com.fasterxml.jackson.core.JsonParser;
+import com.fasterxml.jackson.core.type.TypeReference;
+import com.fasterxml.jackson.databind.DeserializationContext;
+import com.fasterxml.jackson.databind.ObjectMapper;
+import com.fasterxml.jackson.databind.deser.std.StdDeserializer;
+import com.fasterxml.jackson.databind.exc.InvalidNullException;
+import com.fasterxml.jackson.databind.json.JsonMapper;
+import com.fasterxml.jackson.databind.module.SimpleModule;
+import org.opentest4j.AssertionFailedError;
+
+import static org.junit.jupiter.api.Assertions.assertFalse;
+import static org.junit.jupiter.api.Assertions.assertThrows;
+
+// For [databind#5165]
+public class StringArrayDeserializer5165Test
+{
+    static class Dst {
+        private String[] array;
+
+        public String[] getArray() {
+            return array;
+        }
+
+        public void setArray(String[] array) {
+            this.array = array;
+        }
+    }
+
+    // Custom deserializer that converts empty strings to null
+    static class EmptyStringToNullDeserializer extends StdDeserializer<String> {
+        private static final long serialVersionUID = 1L;
+
+        public EmptyStringToNullDeserializer() {
+            super(String.class);
+        }
+
+        @Override
+        public String deserialize(JsonParser p, DeserializationContext ctxt) throws IOException {
+            String value = p.getValueAsString();
+            if (value != null && value.isEmpty()) {
+                return null;
+            }
+            return value;
+        }
+    }
+
+    private ObjectMapper createMapperWithCustomDeserializer() {
+        SimpleModule module = new SimpleModule();
+        module.addDeserializer(String.class, new EmptyStringToNullDeserializer());
+
+        return JsonMapper.builder()
+                .addModule(module)
+                .defaultSetterInfo(JsonSetter.Value.forContentNulls(Nulls.FAIL))
+                .build();
+    }
+
+    @Test
+    public void nullsFailTest() {
+        ObjectMapper mapper = createMapperWithCustomDeserializer();
+
+        assertThrows(
+                AssertionFailedError.class,
+                () -> assertThrows(
+                        InvalidNullException.class,
+                        () -> mapper.readValue("{\"array\":[\"\"]}", new TypeReference<Dst>(){})
+                ),
+                "databind#5165 for StringArrayDeserializer is fixed"
+        );
+    }
+
+    @Test
+    public void nullsSkipTest() throws Exception {
+        SimpleModule module = new SimpleModule();
+        module.addDeserializer(String.class, new EmptyStringToNullDeserializer());
+
+        ObjectMapper mapper = JsonMapper.builder()
+                .addModule(module)
+                .defaultSetterInfo(JsonSetter.Value.forContentNulls(Nulls.SKIP))
+                .build();
+
+        Dst dst = mapper.readValue("{\"array\":[\"\"]}", new TypeReference<Dst>() {});
+
+        assertFalse(dst.getArray() == null || dst.getArray().length == 0, "databind#5165 for StringArrayDeserializer is fixed");
+    }
+}
diff --git a/src/test/java/com/fasterxml/jackson/databind/deser/jdk/StringCollectionDeserializer5165Test.java b/src/test/java/com/fasterxml/jackson/databind/deser/jdk/StringCollectionDeserializer5165Test.java
new file mode 100644
index 0000000000..b0aaf8441f
--- /dev/null
+++ b/src/test/java/com/fasterxml/jackson/databind/deser/jdk/StringCollectionDeserializer5165Test.java
@@ -0,0 +1,94 @@
+package com.fasterxml.jackson.databind.deser.jdk;
+
+import java.io.IOException;
+import java.util.List;
+
+import org.junit.jupiter.api.Test;
+
+import com.fasterxml.jackson.annotation.JsonSetter;
+import com.fasterxml.jackson.annotation.Nulls;
+import com.fasterxml.jackson.core.JsonParser;
+import com.fasterxml.jackson.core.type.TypeReference;
+import com.fasterxml.jackson.databind.DeserializationContext;
+import com.fasterxml.jackson.databind.ObjectMapper;
+import com.fasterxml.jackson.databind.deser.std.StdDeserializer;
+import com.fasterxml.jackson.databind.exc.InvalidNullException;
+import com.fasterxml.jackson.databind.json.JsonMapper;
+import com.fasterxml.jackson.databind.module.SimpleModule;
+import org.opentest4j.AssertionFailedError;
+
+import static org.junit.jupiter.api.Assertions.assertFalse;
+import static org.junit.jupiter.api.Assertions.assertThrows;
+
+// For [databind#5165]
+public class StringCollectionDeserializer5165Test
+{
+    static class Dst {
+        private List<String> list;
+
+        public List<String> getList() {
+            return list;
+        }
+
+        public void setList(List<String> list) {
+            this.list = list;
+        }
+    }
+
+    // Custom deserializer that converts empty strings to null
+    static class EmptyStringToNullDeserializer extends StdDeserializer<String> {
+        private static final long serialVersionUID = 1L;
+
+        public EmptyStringToNullDeserializer() {
+            super(String.class);
+        }
+
+        @Override
+        public String deserialize(JsonParser p, DeserializationContext ctxt) throws IOException {
+            String value = p.getValueAsString();
+            if (value != null && value.isEmpty()) {
+                return null;
+            }
+            return value;
+        }
+    }
+
+    private ObjectMapper createMapperWithCustomDeserializer() {
+        SimpleModule module = new SimpleModule();
+        module.addDeserializer(String.class, new EmptyStringToNullDeserializer());
+
+        return JsonMapper.builder()
+                .addModule(module)
+                .defaultSetterInfo(JsonSetter.Value.forContentNulls(Nulls.FAIL))
+                .build();
+    }
+
+    @Test
+    public void nullsFailTest() {
+        ObjectMapper mapper = createMapperWithCustomDeserializer();
+
+        assertThrows(
+                AssertionFailedError.class,
+                () -> assertThrows(
+                        InvalidNullException.class,
+                        () -> mapper.readValue("{\"list\":[\"\"]}", new TypeReference<Dst>(){})
+                ),
+                "databind#5165 for StringCollectionDeserializer is fixed"
+        );
+    }
+
+    @Test
+    public void nullsSkipTest() throws Exception {
+        SimpleModule module = new SimpleModule();
+        module.addDeserializer(String.class, new EmptyStringToNullDeserializer());
+
+        ObjectMapper mapper = JsonMapper.builder()
+                .addModule(module)
+                .defaultSetterInfo(JsonSetter.Value.forContentNulls(Nulls.SKIP))
+                .build();
+
+        Dst dst = mapper.readValue("{\"list\":[\"\"]}", new TypeReference<Dst>() {});
+
+        assertFalse(dst.getList().isEmpty(), "databind#5165 for StringCollectionDeserializer is fixed");
+    }
+}