diff --git a/exposed-core/api/exposed-core.api b/exposed-core/api/exposed-core.api
index a8beda4dbc..c87a712321 100644
--- a/exposed-core/api/exposed-core.api
+++ b/exposed-core/api/exposed-core.api
@@ -330,6 +330,8 @@ public final class org/jetbrains/exposed/sql/ByteColumnType : org/jetbrains/expo
 	public fun sqlType ()Ljava/lang/String;
 	public fun valueFromDB (Ljava/lang/Object;)Ljava/lang/Byte;
 	public synthetic fun valueFromDB (Ljava/lang/Object;)Ljava/lang/Object;
+	public fun valueToDB (Ljava/lang/Byte;)Ljava/lang/Object;
+	public synthetic fun valueToDB (Ljava/lang/Object;)Ljava/lang/Object;
 }
 
 public final class org/jetbrains/exposed/sql/Case {
diff --git a/exposed-core/src/main/kotlin/org/jetbrains/exposed/sql/ColumnType.kt b/exposed-core/src/main/kotlin/org/jetbrains/exposed/sql/ColumnType.kt
index faeccd0de3..54dacc7b2b 100644
--- a/exposed-core/src/main/kotlin/org/jetbrains/exposed/sql/ColumnType.kt
+++ b/exposed-core/src/main/kotlin/org/jetbrains/exposed/sql/ColumnType.kt
@@ -348,6 +348,15 @@ class ByteColumnType : ColumnType<Byte>() {
         is String -> value.toByte()
         else -> error("Unexpected value of type Byte: $value of ${value::class.qualifiedName}")
     }
+
+    override fun valueToDB(value: Byte?): Any? {
+        return if (currentDialect is SQLServerDialect) {
+            // Workaround for SQL Server JDBC driver mysterious error for in-range values if there's a CHECK constraint
+            value?.toShort()
+        } else {
+            super.valueToDB(value)
+        }
+    }
 }
 
 /**
diff --git a/exposed-core/src/main/kotlin/org/jetbrains/exposed/sql/Table.kt b/exposed-core/src/main/kotlin/org/jetbrains/exposed/sql/Table.kt
index a6b8f540a1..fd7598962f 100644
--- a/exposed-core/src/main/kotlin/org/jetbrains/exposed/sql/Table.kt
+++ b/exposed-core/src/main/kotlin/org/jetbrains/exposed/sql/Table.kt
@@ -688,7 +688,9 @@ open class Table(name: String = "") : ColumnSet(), DdlAware {
     // Numeric columns
 
     /** Creates a numeric column, with the specified [name], for storing 1-byte integers. */
-    fun byte(name: String): Column<Byte> = registerColumn(name, ByteColumnType())
+    fun byte(name: String): Column<Byte> = registerColumn(name, ByteColumnType()).apply {
+        check("${generatedSignedCheckPrefix}byte_$name") { it.between(Byte.MIN_VALUE, Byte.MAX_VALUE) }
+    }
 
     /** Creates a numeric column, with the specified [name], for storing 1-byte unsigned integers.
      *
@@ -1651,14 +1653,19 @@ open class Table(name: String = "") : ColumnSet(), DdlAware {
                         }
                         is SQLServerDialect -> checkConstraints.filterNot { (name, _) ->
                             name.startsWith("${generatedUnsignedCheckPrefix}byte_") ||
-                                name.startsWith(generatedSignedCheckPrefix)
+                                name.startsWith("${generatedSignedCheckPrefix}short")
                         }
                         is PostgreSQLDialect -> checkConstraints.filterNot { (name, _) ->
-                            name.startsWith(generatedSignedCheckPrefix)
+                            name.startsWith("${generatedSignedCheckPrefix}short")
                         }
                         is H2Dialect -> {
                             when (dialect.h2Mode) {
-                                H2Dialect.H2CompatibilityMode.Oracle -> checkConstraints
+                                H2Dialect.H2CompatibilityMode.Oracle -> checkConstraints.filterNot { (name, _) ->
+                                    name.startsWith("${generatedSignedCheckPrefix}byte")
+                                }
+                                H2Dialect.H2CompatibilityMode.PostgreSQL -> checkConstraints.filterNot { (name, _) ->
+                                    name.startsWith("${generatedSignedCheckPrefix}short")
+                                }
                                 else -> checkConstraints.filterNot { (name, _) ->
                                     name.startsWith(generatedSignedCheckPrefix)
                                 }
diff --git a/exposed-core/src/main/kotlin/org/jetbrains/exposed/sql/vendors/OracleDialect.kt b/exposed-core/src/main/kotlin/org/jetbrains/exposed/sql/vendors/OracleDialect.kt
index bfb49ab69e..6da895f8c6 100644
--- a/exposed-core/src/main/kotlin/org/jetbrains/exposed/sql/vendors/OracleDialect.kt
+++ b/exposed-core/src/main/kotlin/org/jetbrains/exposed/sql/vendors/OracleDialect.kt
@@ -13,7 +13,11 @@ import java.util.*
 
 @Suppress("TooManyFunctions")
 internal object OracleDataTypeProvider : DataTypeProvider() {
-    override fun byteType(): String = "SMALLINT"
+    override fun byteType(): String = if (currentDialect.h2Mode == H2Dialect.H2CompatibilityMode.Oracle) {
+        "TINYINT"
+    } else {
+        "NUMBER(3)"
+    }
     override fun ubyteType(): String = "NUMBER(4)"
     override fun shortType(): String = "NUMBER(5)"
     override fun ushortType(): String = "NUMBER(6)"
diff --git a/exposed-core/src/main/kotlin/org/jetbrains/exposed/sql/vendors/SQLServerDialect.kt b/exposed-core/src/main/kotlin/org/jetbrains/exposed/sql/vendors/SQLServerDialect.kt
index 34a3455364..eb88856759 100644
--- a/exposed-core/src/main/kotlin/org/jetbrains/exposed/sql/vendors/SQLServerDialect.kt
+++ b/exposed-core/src/main/kotlin/org/jetbrains/exposed/sql/vendors/SQLServerDialect.kt
@@ -11,8 +11,14 @@ import org.jetbrains.exposed.sql.transactions.TransactionManager
 import java.util.*
 
 internal object SQLServerDataTypeProvider : DataTypeProvider() {
+    override fun byteType(): String = if (currentDialect.h2Mode == H2Dialect.H2CompatibilityMode.SQLServer) {
+        "TINYINT"
+    } else {
+        "SMALLINT"
+    }
+
     override fun ubyteType(): String {
-        return if ((currentDialect as? H2Dialect)?.h2Mode == H2Dialect.H2CompatibilityMode.SQLServer) {
+        return if (currentDialect.h2Mode == H2Dialect.H2CompatibilityMode.SQLServer) {
             "SMALLINT"
         } else {
             "TINYINT"
@@ -32,7 +38,7 @@ internal object SQLServerDataTypeProvider : DataTypeProvider() {
     override fun uuidToDB(value: UUID): Any = value.toString()
     override fun dateTimeType(): String = "DATETIME2"
     override fun timestampWithTimeZoneType(): String =
-        if ((currentDialect as? H2Dialect)?.h2Mode == H2Dialect.H2CompatibilityMode.SQLServer) {
+        if (currentDialect.h2Mode == H2Dialect.H2CompatibilityMode.SQLServer) {
             "TIMESTAMP(9) WITH TIME ZONE"
         } else {
             "DATETIMEOFFSET"
diff --git a/exposed-tests/src/test/kotlin/org/jetbrains/exposed/sql/tests/shared/types/NumericColumnTypesTests.kt b/exposed-tests/src/test/kotlin/org/jetbrains/exposed/sql/tests/shared/types/NumericColumnTypesTests.kt
index f4ca7e5a38..05fa3f3322 100644
--- a/exposed-tests/src/test/kotlin/org/jetbrains/exposed/sql/tests/shared/types/NumericColumnTypesTests.kt
+++ b/exposed-tests/src/test/kotlin/org/jetbrains/exposed/sql/tests/shared/types/NumericColumnTypesTests.kt
@@ -39,4 +39,39 @@ class NumericColumnTypesTests : DatabaseTestsBase() {
             }
         }
     }
+
+    @Test
+    fun testByteAcceptsOnlyAllowedRange() {
+        val testTable = object : Table("test_table") {
+            val byte = byte("byte")
+        }
+
+        withTables(testTable) { testDb ->
+            val columnName = testTable.byte.nameInDatabaseCase()
+            val ddlEnding = when (testDb) {
+                in TestDB.ALL_POSTGRES_LIKE, TestDB.ORACLE, TestDB.SQLITE, TestDB.SQLSERVER ->
+                    "CHECK ($columnName BETWEEN ${Byte.MIN_VALUE} and ${Byte.MAX_VALUE}))"
+                else -> "($columnName ${testTable.byte.columnType} NOT NULL)"
+            }
+            assertTrue(testTable.ddl.single().endsWith(ddlEnding, ignoreCase = true))
+
+            testTable.insert { it[byte] = Byte.MIN_VALUE }
+            testTable.insert { it[byte] = Byte.MAX_VALUE }
+            assertEquals(2, testTable.select(testTable.byte).count())
+
+            val tableName = testTable.nameInDatabaseCase()
+            assertFailAndRollback(
+                message = "CHECK constraint violation or out-of-range error for MySQL, MariaDB, and H2 (except for H2_V2_PSQL)"
+            ) {
+                val outOfRangeValue = Byte.MIN_VALUE - 1
+                exec("INSERT INTO $tableName ($columnName) VALUES ($outOfRangeValue)")
+            }
+            assertFailAndRollback(
+                message = "CHECK constraint violation or out-of-range error for MySQL, MariaDB, and H2 (except for H2_V2_PSQL)"
+            ) {
+                val outOfRangeValue = Byte.MAX_VALUE + 1
+                exec("INSERT INTO $tableName ($columnName) VALUES ($outOfRangeValue)")
+            }
+        }
+    }
 }