diff --git a/src/main/java/com/fasterxml/jackson/databind/deser/std/ObjectArrayDeserializer.java b/src/main/java/com/fasterxml/jackson/databind/deser/std/ObjectArrayDeserializer.java
index 61cc466335..d6e194c634 100644
--- a/src/main/java/com/fasterxml/jackson/databind/deser/std/ObjectArrayDeserializer.java
+++ b/src/main/java/com/fasterxml/jackson/databind/deser/std/ObjectArrayDeserializer.java
@@ -211,10 +211,19 @@ public Object deserialize(JsonParser p, DeserializationContext ctxt)
                     if (_skipNullValues) {
                         continue;
                     }
-                    value = _nullProvider.getNullValue(ctxt);
+                    value = null;
                 } else {
                     value = _deserializeNoNullChecks(p, ctxt);
                 }
+
+                if (value == null) {
+                    value = _nullProvider.getNullValue(ctxt);
+
+                    if (value == null && _skipNullValues) {
+                        continue;
+                    }
+                }
+
                 if (ix >= chunk.length) {
                     chunk = buffer.appendCompletedChunk(chunk);
                     ix = 0;
@@ -275,10 +284,19 @@ public Object deserialize(JsonParser p, DeserializationContext ctxt,
                     if (_skipNullValues) {
                         continue;
                     }
-                    value = _nullProvider.getNullValue(ctxt);
+                    value = null;
                 } else {
                     value = _deserializeNoNullChecks(p, ctxt);
                 }
+
+                if (value == null) {
+                    value = _nullProvider.getNullValue(ctxt);
+
+                    if (value == null && _skipNullValues) {
+                        continue;
+                    }
+                }
+
                 if (ix >= chunk.length) {
                     chunk = buffer.appendCompletedChunk(chunk);
                     ix = 0;
@@ -346,7 +364,7 @@ protected Object handleNonArray(JsonParser p, DeserializationContext ctxt)
             if (_skipNullValues) {
                 return _emptyValue;
             }
-            value = _nullProvider.getNullValue(ctxt);
+            value = null;
         } else {
             if (p.hasToken(JsonToken.VALUE_STRING)) {
                 String textValue = p.getText();
@@ -371,6 +389,15 @@ protected Object handleNonArray(JsonParser p, DeserializationContext ctxt)
 
             value = _deserializeNoNullChecks(p, ctxt);
         }
+
+        if (value == null) {
+            value = _nullProvider.getNullValue(ctxt);
+
+            if (value == null && _skipNullValues) {
+                return _emptyValue;
+            }
+        }
+
         // Ok: bit tricky, since we may want T[], not just Object[]
         Object[] result;
 
@@ -399,4 +426,3 @@ protected Object _deserializeNoNullChecks(JsonParser p, DeserializationContext c
         return _elementDeserializer.deserializeWithType(p, ctxt, _elementTypeDeserializer);
     }
 }
-
diff --git a/src/main/java/com/fasterxml/jackson/databind/deser/std/StringArrayDeserializer.java b/src/main/java/com/fasterxml/jackson/databind/deser/std/StringArrayDeserializer.java
index 864299d326..aafdc80230 100644
--- a/src/main/java/com/fasterxml/jackson/databind/deser/std/StringArrayDeserializer.java
+++ b/src/main/java/com/fasterxml/jackson/databind/deser/std/StringArrayDeserializer.java
@@ -162,10 +162,17 @@ public String[] deserialize(JsonParser p, DeserializationContext ctxt) throws IO
                         if (_skipNullValues) {
                             continue;
                         }
-                        value = (String) _nullProvider.getNullValue(ctxt);
                     } else {
                         value = _parseString(p, ctxt, _nullProvider);
                     }
+
+                    if (value == null) {
+                        value = (String) _nullProvider.getNullValue(ctxt);
+
+                        if (value == null && _skipNullValues) {
+                            continue;
+                        }
+                    }
                 }
                 if (ix >= chunk.length) {
                     chunk = buffer.appendCompletedChunk(chunk);
@@ -219,13 +226,22 @@ private String[] _deserializeCustom(JsonParser p, DeserializationContext ctxt,
                         if (_skipNullValues) {
                             continue;
                         }
-                        value = (String) _nullProvider.getNullValue(ctxt);
+                        value = null;
                     } else {
                         value = deser.deserialize(p, ctxt);
                     }
                 } else {
                     value = deser.deserialize(p, ctxt);
                 }
+
+                if (value == null) {
+                    value = (String) _nullProvider.getNullValue(ctxt);
+
+                    if (value == null && _skipNullValues) {
+                        continue;
+                    }
+                }
+
                 if (ix >= chunk.length) {
                     chunk = buffer.appendCompletedChunk(chunk);
                     ix = 0;
@@ -283,10 +299,17 @@ public String[] deserialize(JsonParser p, DeserializationContext ctxt,
                         if (_skipNullValues) {
                             return NO_STRINGS;
                         }
-                        value = (String) _nullProvider.getNullValue(ctxt);
                     } else {
                         value = _parseString(p, ctxt, _nullProvider);
                     }
+
+                    if (value == null) {
+                        value = (String) _nullProvider.getNullValue(ctxt);
+
+                        if (value == null && _skipNullValues) {
+                            continue;
+                        }
+                    }
                 }
                 if (ix >= chunk.length) {
                     chunk = buffer.appendCompletedChunk(chunk);
diff --git a/src/main/java/com/fasterxml/jackson/databind/deser/std/StringCollectionDeserializer.java b/src/main/java/com/fasterxml/jackson/databind/deser/std/StringCollectionDeserializer.java
index d4984a084b..acfb21f32a 100644
--- a/src/main/java/com/fasterxml/jackson/databind/deser/std/StringCollectionDeserializer.java
+++ b/src/main/java/com/fasterxml/jackson/databind/deser/std/StringCollectionDeserializer.java
@@ -213,10 +213,18 @@ public Collection<String> deserialize(JsonParser p, DeserializationContext ctxt,
                     if (_skipNullValues) {
                         continue;
                     }
-                    value = (String) _nullProvider.getNullValue(ctxt);
                 } else {
                     value = _parseString(p, ctxt, _nullProvider);
                 }
+
+                if (value == null) {
+                    value = (String) _nullProvider.getNullValue(ctxt);
+
+                    if (value == null && _skipNullValues) {
+                        continue;
+                    }
+                }
+
                 result.add(value);
             }
         } catch (Exception e) {
@@ -246,13 +254,22 @@ private Collection<String> deserializeUsingCustom(JsonParser p, DeserializationC
                         if (_skipNullValues) {
                             continue;
                         }
-                        value = (String) _nullProvider.getNullValue(ctxt);
+                        value = null;
                     } else {
                         value = deser.deserialize(p, ctxt);
                     }
                 } else {
                     value = deser.deserialize(p, ctxt);
                 }
+
+                if (value == null) {
+                    value = (String) _nullProvider.getNullValue(ctxt);
+
+                    if (value == null && _skipNullValues) {
+                        continue;
+                    }
+                }
+
                 result.add(value);
             }
         } catch (Exception e) {
@@ -297,7 +314,7 @@ private final Collection<String> handleNonArray(JsonParser p, DeserializationCon
             if (_skipNullValues) {
                 return result;
             }
-            value = (String) _nullProvider.getNullValue(ctxt);
+            value = null;
         } else {
             if (p.hasToken(JsonToken.VALUE_STRING)) {
                 String textValue = p.getText();
@@ -326,6 +343,15 @@ private final Collection<String> handleNonArray(JsonParser p, DeserializationCon
                 throw JsonMappingException.wrapWithPath(e, result, result.size());
             }
         }
+
+        if (value == null) {
+            value = (String) _nullProvider.getNullValue(ctxt);
+
+            if (value == null && _skipNullValues) {
+                return result;
+            }
+        }
+
         result.add(value);
         return result;
     }
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..c4e007eaef
--- /dev/null
+++ b/src/test/java/com/fasterxml/jackson/databind/deser/jdk/ObjectArrayDeserializer5165Test.java
@@ -0,0 +1,52 @@
+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 static org.junit.jupiter.api.Assertions.assertEquals;
+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(
+                InvalidNullException.class,
+                () -> mapper.readValue("{\"array\":[\"\"]}", new TypeReference<Dst>(){})
+        );
+    }
+
+    @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>() {});
+
+        assertEquals(0, dst.getArray().length, "Null values should be skipped");
+    }
+}
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..8d65e86c86
--- /dev/null
+++ b/src/test/java/com/fasterxml/jackson/databind/deser/jdk/StringArrayDeserializer5165Test.java
@@ -0,0 +1,88 @@
+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 static org.junit.jupiter.api.Assertions.assertEquals;
+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(
+                InvalidNullException.class,
+                () -> mapper.readValue("{\"array\":[\"\"]}", new TypeReference<Dst>(){})
+        );
+    }
+
+    @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>() {});
+
+        assertEquals(0, dst.getArray().length, "Null values should be skipped");
+    }
+}
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..8a93eb2fc9
--- /dev/null
+++ b/src/test/java/com/fasterxml/jackson/databind/deser/jdk/StringCollectionDeserializer5165Test.java
@@ -0,0 +1,89 @@
+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 static org.junit.jupiter.api.Assertions.assertThrows;
+import static org.junit.jupiter.api.Assertions.assertTrue;
+
+// 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(
+                InvalidNullException.class,
+                () -> mapper.readValue("{\"list\":[\"\"]}", new TypeReference<Dst>(){})
+        );
+    }
+
+    @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>() {});
+
+        assertTrue(dst.getList().isEmpty(), "Null values should be skipped");
+    }
+}
diff --git a/src/test/java/com/fasterxml/jackson/databind/tofix/EnumSetDeserializer5165Test.java b/src/test/java/com/fasterxml/jackson/databind/tofix/EnumSetDeserializer5165Test.java
new file mode 100644
index 0000000000..49542266a6
--- /dev/null
+++ b/src/test/java/com/fasterxml/jackson/databind/tofix/EnumSetDeserializer5165Test.java
@@ -0,0 +1,96 @@
+package com.fasterxml.jackson.databind.tofix;
+
+import java.io.IOException;
+import java.util.EnumSet;
+
+import com.fasterxml.jackson.databind.testutil.failure.JacksonTestFailureExpected;
+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 static org.junit.jupiter.api.Assertions.assertThrows;
+import static org.junit.jupiter.api.Assertions.assertTrue;
+
+// 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();
+    }
+
+    @JacksonTestFailureExpected
+    @Test
+    public void nullsFailTest() {
+        ObjectMapper mapper = createMapperWithCustomDeserializer();
+
+        assertThrows(
+                InvalidNullException.class,
+                () -> mapper.readValue("{\"set\":[\"\"]}", new TypeReference<Dst>(){})
+        );
+    }
+
+    @JacksonTestFailureExpected
+    @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>() {});
+
+        assertTrue(dst.getSet().isEmpty(), "Null values should be skipped");
+    }
+}