diff --git a/core/src/main/kotlin/io/specmatic/core/pattern/StringPattern.kt b/core/src/main/kotlin/io/specmatic/core/pattern/StringPattern.kt
index 11ae5370b..30d76a0b5 100644
--- a/core/src/main/kotlin/io/specmatic/core/pattern/StringPattern.kt
+++ b/core/src/main/kotlin/io/specmatic/core/pattern/StringPattern.kt
@@ -25,8 +25,9 @@ data class StringPattern(
             throw IllegalArgumentException("maxLength cannot be less than minLength")
         }
         regex?.let {
-            regexMinLengthValidation(it)
-            regexMaxLengthValidation(it)
+            val regexWithoutCaretAndDollar = it.removePrefix("^").removeSuffix("$")
+            regexMinLengthValidation(regexWithoutCaretAndDollar)
+            regexMaxLengthValidation(regexWithoutCaretAndDollar)
         }
 
     }
@@ -46,10 +47,11 @@ data class StringPattern(
 
     private fun regexMaxLengthValidation(it: String) {
         maxLength?.let { maxLen ->
-            val regexWithoutCaretAndDollar = it.removePrefix("^").removeSuffix("$")
-            runCatching {
-                StringValue(generateFromRegex(regexWithoutCaretAndDollar, 5, maxLen + 1))
-            }.getOrNull() ?: throw IllegalArgumentException("Invalid Regex - max cannot be more than regex max size")
+            val generatedString = generateFromRegex(it, maxLen+1)
+
+            if (generatedString.length > maxLen) {
+                throw IllegalArgumentException("Invalid Regex - max cannot be more than regex max size")
+            }
         }
     }
 
@@ -185,7 +187,7 @@ data class StringPattern(
     override val pattern: Any = "(string)"
     override fun toString(): String = pattern.toString()
 
-    private fun generateFromRegex(regexWithoutCaretAndDollar: String, minLength: Int, maxLength: Int?): String =
+    private fun generateFromRegex(regexWithoutCaretAndDollar: String, minLength: Int, maxLength: Int? = null): String =
         maxLength?.let {
             Generex(regexWithoutCaretAndDollar).random(minLength, it)
         } ?: Generex(regexWithoutCaretAndDollar).random(minLength)
diff --git a/core/src/test/kotlin/io/specmatic/core/pattern/StringPatternTest.kt b/core/src/test/kotlin/io/specmatic/core/pattern/StringPatternTest.kt
index ccaadb1d8..73d4ef33a 100644
--- a/core/src/test/kotlin/io/specmatic/core/pattern/StringPatternTest.kt
+++ b/core/src/test/kotlin/io/specmatic/core/pattern/StringPatternTest.kt
@@ -87,7 +87,7 @@ internal class StringPatternTest {
         fun regexMinLengthAndMaxLengthAndExpectedLength(): Stream<Arguments> {
             return Stream.of(
                 Arguments.of("^[a-z]*\$", null, null, 5),
-                Arguments.of("^[a-z0-9]{6,}\$", 3, 10, 6),
+                Arguments.of("^[a-z0-9]{6,10}\$", 3, 10, 6),
                 Arguments.of(null, 1, 10, 1),
             )
         }
@@ -205,16 +205,54 @@ internal class StringPatternTest {
         val result = StringPattern(
             minLength = minLength,
             maxLength = maxLength,
-            regex = "^[^0-9]*$"
+            regex = "^[^0-9]{15}$"
         ).negativeBasedOn(Row(), Resolver()).map { it.value }.toList()
 
         assertThat(
             result.filterIsInstance<StringPattern>().filter {
-                it.regex == "^[^0-9]*\$_"
+                it.regex == "^[^0-9]{15}\$_"
             }
         ).hasSize(1)
     }
 
+    @Test
+    @Tag(GENERATION)
+    fun `regex sould throw validation issue for patterns less than min size as per api contract`() {
+        val minLength = 2
+        val maxLength = 15
+
+        val result = runCatching {
+            StringPattern(
+                minLength = minLength,
+                maxLength = maxLength,
+                regex = "^.{0,4}$"
+            ).negativeBasedOn(Row(), Resolver()).map { it.value }.toList()
+        }
+
+        result.onFailure { exception ->
+            assertThat(exception.message).isEqualTo("Invalid Regex - min cannot be less than regex least size")
+        }
+    }
+
+    @Test
+    @Tag(GENERATION)
+    fun `regex sould throw validation issue for patterns more than max size as per api contract`() {
+        val minLength = 2
+        val maxLength = 15
+
+        val result = runCatching {
+            StringPattern(
+                minLength = minLength,
+                maxLength = maxLength,
+                regex = "^.{2,14}$"
+            ).negativeBasedOn(Row(), Resolver()).map { it.value }.toList()
+        }
+
+        result.onFailure { exception ->
+            assertThat(exception.message).isEqualTo("Invalid Regex - max cannot be more than regex max size")
+        }
+    }
+
     @Test
     @Tag(GENERATION)
     fun `should exclude data type based negatives when withDataTypeNegatives config is false`() {
@@ -224,7 +262,7 @@ internal class StringPatternTest {
         val result = StringPattern(
             minLength = minLength,
             maxLength = maxLength,
-            regex = "^[^0-9]*$"
+            regex = "^[^0-9]{15}$"
         ).negativeBasedOn(
             Row(),
             Resolver(),
@@ -239,7 +277,7 @@ internal class StringPatternTest {
         ).hasSize(0)
 
         assertThat(
-            result.filterIsInstance<StringPattern>().filter { it.regex == "^[^0-9]*\$_" }
+            result.filterIsInstance<StringPattern>().filter { it.regex == "^[^0-9]{15}\$_" }
         ).hasSize(1)
 
         assertThat(