diff --git a/exposed-core/src/main/kotlin/org/jetbrains/exposed/sql/SQLExpressionBuilder.kt b/exposed-core/src/main/kotlin/org/jetbrains/exposed/sql/SQLExpressionBuilder.kt
index 7d0e6702a0..427f98686b 100644
--- a/exposed-core/src/main/kotlin/org/jetbrains/exposed/sql/SQLExpressionBuilder.kt
+++ b/exposed-core/src/main/kotlin/org/jetbrains/exposed/sql/SQLExpressionBuilder.kt
@@ -921,38 +921,13 @@ interface ISqlExpressionBuilder {
 
     /** Returns the specified [value] as a query parameter of type [T]. */
     @Suppress("UNCHECKED_CAST")
-    fun <T, S : T?> ExpressionWithColumnType<in S>.wrap(value: T): QueryParameter<T> = when (value) {
-        is Boolean -> booleanParam(value)
-        is Byte -> byteParam(value)
-        is UByte -> ubyteParam(value)
-        is Short -> shortParam(value)
-        is UShort -> ushortParam(value)
-        is Int -> intParam(value)
-        is UInt -> uintParam(value)
-        is Long -> longParam(value)
-        is ULong -> ulongParam(value)
-        is Float -> floatParam(value)
-        is Double -> doubleParam(value)
-        is String -> QueryParameter(value, columnType as IColumnType<T & Any>) // String value should inherit from column
-        else -> QueryParameter(value, columnType as IColumnType<T & Any>)
-    } as QueryParameter<T>
+    fun <T, S : T?> ExpressionWithColumnType<in S>.wrap(value: T): QueryParameter<T> =
+        QueryParameter(value, columnType as IColumnType<T & Any>)
 
     /** Returns the specified [value] as a literal of type [T]. */
     @Suppress("UNCHECKED_CAST", "ComplexMethod")
-    fun <T, S : T?> ExpressionWithColumnType<S>.asLiteral(value: T): LiteralOp<T> = when (value) {
-        is Boolean -> booleanLiteral(value)
-        is Byte -> byteLiteral(value)
-        is UByte -> ubyteLiteral(value)
-        is Short -> shortLiteral(value)
-        is UShort -> ushortLiteral(value)
-        is Int -> intLiteral(value)
-        is UInt -> uintLiteral(value)
-        is Long -> longLiteral(value)
-        is ULong -> ulongLiteral(value)
-        is Float -> floatLiteral(value)
-        is Double -> doubleLiteral(value)
-        is String -> stringLiteral(value)
-        is ByteArray -> stringLiteral(value.toString(Charsets.UTF_8))
+    fun <T, S : T?> ExpressionWithColumnType<S>.asLiteral(value: T): LiteralOp<T> = when {
+        value is ByteArray && columnType is BasicBinaryColumnType -> stringLiteral(value.toString(Charsets.UTF_8))
         else -> LiteralOp(columnType as IColumnType<T & Any>, value)
     } as LiteralOp<T>
 
diff --git a/exposed-json/src/main/kotlin/org/jetbrains/exposed/sql/json/JsonConditions.kt b/exposed-json/src/main/kotlin/org/jetbrains/exposed/sql/json/JsonConditions.kt
index 1b1442ff00..bab311efd4 100644
--- a/exposed-json/src/main/kotlin/org/jetbrains/exposed/sql/json/JsonConditions.kt
+++ b/exposed-json/src/main/kotlin/org/jetbrains/exposed/sql/json/JsonConditions.kt
@@ -1,13 +1,7 @@
 package org.jetbrains.exposed.sql.json
 
-import org.jetbrains.exposed.sql.ComplexExpression
-import org.jetbrains.exposed.sql.Expression
-import org.jetbrains.exposed.sql.ExpressionWithColumnType
-import org.jetbrains.exposed.sql.IColumnType
-import org.jetbrains.exposed.sql.Op
-import org.jetbrains.exposed.sql.QueryBuilder
+import org.jetbrains.exposed.sql.*
 import org.jetbrains.exposed.sql.SqlExpressionBuilder.asLiteral
-import org.jetbrains.exposed.sql.stringLiteral
 import org.jetbrains.exposed.sql.vendors.currentDialect
 
 // Operator Classes
@@ -69,6 +63,7 @@ fun ExpressionWithColumnType<*>.contains(candidate: Expression<*>, path: String?
  */
 fun <T> ExpressionWithColumnType<*>.contains(candidate: T, path: String? = null): Contains = when (candidate) {
     is Iterable<*>, is Array<*> -> Contains(this, stringLiteral(asLiteral(candidate).toString()), path, columnType)
+    is String -> Contains(this, stringLiteral(candidate), path, columnType)
     else -> Contains(this, asLiteral(candidate), path, columnType)
 }
 
diff --git a/exposed-tests/src/test/kotlin/org/jetbrains/exposed/sql/tests/shared/types/BooleanColumnTypeTests.kt b/exposed-tests/src/test/kotlin/org/jetbrains/exposed/sql/tests/shared/types/BooleanColumnTypeTests.kt
index ef46ddac73..d021c52c56 100644
--- a/exposed-tests/src/test/kotlin/org/jetbrains/exposed/sql/tests/shared/types/BooleanColumnTypeTests.kt
+++ b/exposed-tests/src/test/kotlin/org/jetbrains/exposed/sql/tests/shared/types/BooleanColumnTypeTests.kt
@@ -49,4 +49,60 @@ class BooleanColumnTypeTests : DatabaseTestsBase() {
             assertEquals(idTrue, resultTrue?.get(BooleanTable.id))
         }
     }
+
+    @Test
+    fun testCustomCharBooleanColumnType() {
+        val tester = object : Table("tester") {
+            val charBooleanColumn = charBoolean("charBooleanColumn")
+            val charBooleanColumnWithDefault = charBoolean("charBooleanColumnWithDefault")
+                .default(false)
+        }
+
+        withDb {
+            try {
+                SchemaUtils.create(tester)
+
+                tester.insert {
+                    it[charBooleanColumn] = true
+                }
+
+                assertEquals(
+                    1,
+                    tester.select(tester.charBooleanColumn)
+                        .where { tester.charBooleanColumn eq true }
+                        .andWhere { tester.charBooleanColumnWithDefault eq false }
+                        .count()
+                )
+            } finally {
+                SchemaUtils.drop(tester)
+            }
+        }
+    }
+
+    class CharBooleanColumnType(
+        private val characterColumnType: VarCharColumnType = VarCharColumnType(1),
+    ) : ColumnType<Boolean>() {
+        override fun sqlType(): String = characterColumnType.preciseType()
+
+        override fun valueFromDB(value: Any): Boolean =
+            when (characterColumnType.valueFromDB(value)) {
+                "Y" -> true
+                else -> false
+            }
+
+        override fun valueToDB(value: Boolean?): Any? =
+            characterColumnType.valueToDB(value.toChar().toString())
+
+        override fun nonNullValueToString(value: Boolean): String =
+            characterColumnType.nonNullValueToString(value.toChar().toString())
+
+        private fun Boolean?.toChar() = when (this) {
+            true -> 'Y'
+            false -> 'N'
+            else -> ' '
+        }
+    }
+
+    fun Table.charBoolean(name: String): Column<Boolean> =
+        registerColumn(name, CharBooleanColumnType())
 }