diff --git a/sql/catalyst/src/main/scala/org/apache/spark/sql/catalyst/analysis/ApplyCharTypePaddingHelper.scala b/sql/catalyst/src/main/scala/org/apache/spark/sql/catalyst/analysis/ApplyCharTypePaddingHelper.scala
index 26c85469e3f32..989581dc7fde1 100644
--- a/sql/catalyst/src/main/scala/org/apache/spark/sql/catalyst/analysis/ApplyCharTypePaddingHelper.scala
+++ b/sql/catalyst/src/main/scala/org/apache/spark/sql/catalyst/analysis/ApplyCharTypePaddingHelper.scala
@@ -21,6 +21,7 @@ import org.apache.spark.sql.catalyst.expressions.{
   Alias,
   Attribute,
   BinaryComparison,
+  Cast,
   Expression,
   In,
   Literal,
@@ -48,6 +49,19 @@ object ApplyCharTypePaddingHelper {
     }
   }
 
+  private object StringAttrOrOuterRef {
+    def unapply(e: Expression): Option[(Expression, Attribute)] = e match {
+      case attr @ AttrOrOuterRef(a) if attr.dataType.isInstanceOf[StringType] =>
+        Some(attr -> a)
+      case cast @ Cast(AttrOrOuterRef(a), _: StringType, _, _)
+          if a.dataType.isInstanceOf[StringType] &&
+            !cast.containsTag(Cast.USER_SPECIFIED_CAST) =>
+        Some(cast -> a)
+      case _ =>
+        None
+    }
+  }
+
   private[sql] def readSidePadding(
       relation: LogicalPlan,
       cleanedRelation: () => LogicalPlan): (LogicalPlan, Seq[(Attribute, Attribute)]) = {
@@ -98,23 +112,25 @@ object ApplyCharTypePaddingHelper {
           }
           .getOrElse(b)
 
-      case i @ In(e @ AttrOrOuterRef(attr), list)
-          if i.resolved && attr.dataType.isInstanceOf[StringType] && list.forall(_.foldable) =>
+      case i @ In(StringAttrOrOuterRef(e, attr), list)
+          if i.resolved && list.forall(_.foldable) =>
         CharVarcharUtils
           .getRawType(attr.metadata)
           .flatMap {
             case c: CharType =>
-              val (nulls, literalChars) =
-                list.map(_.eval().asInstanceOf[UTF8String]).partition(_ == null)
-              val literalCharLengths = literalChars.map(_.numChars())
+              val literalValues = list.map(lit => lit -> lit.eval().asInstanceOf[UTF8String])
+              val literalCharLengths = literalValues.collect {
+                case (_, value) if value != null => value.numChars()
+              }
               val targetLen = (c.length +: literalCharLengths).max
               Some(
                 i.copy(
                   value = addPadding(e, c.length, targetLen, alwaysPad = padCharCol),
-                  list = list.zip(literalCharLengths).map {
-                      case (lit, charLength) =>
-                        addPadding(lit, charLength, targetLen, alwaysPad = false)
-                    } ++ nulls.map(Literal.create(_, StringType))
+                  list = literalValues.map {
+                    case (lit, null) => lit
+                    case (lit, value) =>
+                      addPadding(lit, value.numChars(), targetLen, alwaysPad = false)
+                  }
                 )
               )
             case _ => None
diff --git a/sql/catalyst/src/main/scala/org/apache/spark/sql/catalyst/util/CharVarcharUtils.scala b/sql/catalyst/src/main/scala/org/apache/spark/sql/catalyst/util/CharVarcharUtils.scala
index 00adcfe69bc56..930c19858aa25 100644
--- a/sql/catalyst/src/main/scala/org/apache/spark/sql/catalyst/util/CharVarcharUtils.scala
+++ b/sql/catalyst/src/main/scala/org/apache/spark/sql/catalyst/util/CharVarcharUtils.scala
@@ -337,12 +337,21 @@ object CharVarcharUtils extends Logging with SparkCharVarcharUtils {
           val fieldExpr = GetStructField(expr, i, Some(field.name))
           val padded = padCharToTargetLength(
             fieldExpr, field.dataType, targets(i).dataType, alwaysPad)
-          needPadding = padded.isDefined
+          needPadding = needPadding || padded.isDefined
           createStructExprs += Literal(field.name)
           createStructExprs += padded.getOrElse(fieldExpr)
           i += 1
         }
-        if (needPadding) Some(CreateNamedStruct(createStructExprs.toSeq)) else None
+        if (needPadding) {
+          val struct = CreateNamedStruct(createStructExprs.toSeq)
+          if (expr.nullable) {
+            Some(If(IsNull(expr), Literal(null, struct.dataType), struct))
+          } else {
+            Some(struct)
+          }
+        } else {
+          None
+        }
 
       case (ArrayType(et, containsNull), ArrayType(target, _)) =>
         val param = NamedLambdaVariable("x", replaceCharVarcharWithString(et), containsNull)
diff --git a/sql/core/src/test/scala/org/apache/spark/sql/CharVarcharTestSuite.scala b/sql/core/src/test/scala/org/apache/spark/sql/CharVarcharTestSuite.scala
index 39694ad3d6869..75104c2b5a7dd 100644
--- a/sql/core/src/test/scala/org/apache/spark/sql/CharVarcharTestSuite.scala
+++ b/sql/core/src/test/scala/org/apache/spark/sql/CharVarcharTestSuite.scala
@@ -681,6 +681,52 @@ trait CharVarcharTestSuite extends QueryTest {
     }
   }
 
+  test("SPARK-59278: CHAR padding preserves IN list order around NULL") {
+    withTable("t") {
+      sql(s"CREATE TABLE t(c CHAR(5)) USING $format")
+      sql("INSERT INTO t VALUES ('a')")
+
+      checkAnswer(sql("SELECT c IN (NULL, 'a') FROM t"), Row(true))
+      checkAnswer(sql("SELECT c IN ('x', NULL, 'a') FROM t"), Row(true))
+      checkAnswer(sql("SELECT c IN (NULL, 'x') FROM t"), Row(null))
+      checkAnswer(sql("SELECT c NOT IN (NULL, 'a') FROM t"), Row(false))
+      checkAnswer(sql("SELECT c NOT IN (NULL, 'x') FROM t"), Row(null))
+
+      withSQLConf(SQLConf.OPTIMIZER_INSET_CONVERSION_THRESHOLD.key -> "1") {
+        checkAnswer(sql("SELECT c IN (NULL, 'a', 'b') FROM t"), Row(true))
+        checkAnswer(sql("SELECT c IN (NULL, 'x', 'y') FROM t"), Row(null))
+      }
+
+      // A user-specified cast deliberately opts into STRING comparison and must not trigger the
+      // implicit CHAR padding rewrite.
+      checkAnswer(sql("SELECT CAST(c AS STRING) IN ('a') FROM t"), Row(false))
+      checkAnswer(sql("SELECT CAST(c AS STRING) IN (NULL, 'a') FROM t"), Row(null))
+    }
+  }
+
+  test("SPARK-59278: CHAR padding accumulates across nested struct fields") {
+    withTable("t1", "t2") {
+      sql(s"CREATE TABLE t1(s STRUCT<a: CHAR(2), b: CHAR(5)>) USING $format")
+      sql(s"CREATE TABLE t2(s STRUCT<a: CHAR(4), b: CHAR(5)>) USING $format")
+      sql("INSERT INTO t1 SELECT named_struct('a', 'a', 'b', 'b')")
+      sql("INSERT INTO t2 SELECT named_struct('a', 'a', 'b', 'b')")
+
+      checkAnswer(sql("SELECT t1.s = t2.s FROM t1 CROSS JOIN t2"), Row(true))
+
+      sql("INSERT OVERWRITE t1 SELECT CAST(NULL AS STRUCT<a: STRING, b: STRING>)")
+      sql("INSERT OVERWRITE t2 SELECT CAST(NULL AS STRUCT<a: STRING, b: STRING>)")
+      checkAnswer(sql("SELECT t1.s = t2.s FROM t1 CROSS JOIN t2"), Row(null))
+      checkAnswer(sql("SELECT t1.s <=> t2.s FROM t1 CROSS JOIN t2"), Row(true))
+
+      sql(
+        """INSERT OVERWRITE t2
+          |SELECT named_struct(
+          |  'a', CAST(NULL AS STRING),
+          |  'b', CAST(NULL AS STRING))""".stripMargin)
+      checkAnswer(sql("SELECT t1.s <=> t2.s FROM t1 CROSS JOIN t2"), Row(false))
+    }
+  }
+
   test("SPARK-35359: create table and insert data over length values") {
     Seq("char", "varchar").foreach { typ =>
       withSQLConf((SQLConf.LEGACY_CHAR_VARCHAR_AS_STRING.key, "true")) {