diff --git a/src/Schema/Exception/NotEnoughValidSchemas.php b/src/Schema/Exception/NotEnoughValidSchemas.php
new file mode 100644
index 00000000..f17e281d
--- /dev/null
+++ b/src/Schema/Exception/NotEnoughValidSchemas.php
@@ -0,0 +1,41 @@
+<?php
+
+declare(strict_types=1);
+
+namespace League\OpenAPIValidation\Schema\Exception;
+
+use Throwable;
+
+class NotEnoughValidSchemas extends KeywordMismatch
+{
+    /** @var Throwable[] */
+    protected $innerExceptions = [];
+
+    /**
+     * @param mixed       $data
+     * @param Throwable[] $innerExceptions
+     *
+     * @return self
+     */
+    public static function fromKeywordWithInnerExceptions(
+        string $keyword,
+        $data,
+        array $innerExceptions,
+        ?string $message = null
+    ) : KeywordMismatch {
+        $instance                  = new self('Keyword validation failed: ' . $message, 0);
+        $instance->keyword         = $keyword;
+        $instance->data            = $data;
+        $instance->innerExceptions = $innerExceptions;
+
+        return $instance;
+    }
+
+    /**
+     * @return Throwable[]
+     */
+    public function innerExceptions() : array
+    {
+        return $this->innerExceptions;
+    }
+}
diff --git a/src/Schema/Exception/TooManyValidSchemas.php b/src/Schema/Exception/TooManyValidSchemas.php
new file mode 100644
index 00000000..619cea14
--- /dev/null
+++ b/src/Schema/Exception/TooManyValidSchemas.php
@@ -0,0 +1,41 @@
+<?php
+
+declare(strict_types=1);
+
+namespace League\OpenAPIValidation\Schema\Exception;
+
+use cebe\openapi\spec\Schema;
+
+class TooManyValidSchemas extends KeywordMismatch
+{
+    /** @var Schema[] */
+    protected $validSchemas = [];
+
+    /**
+     * @param mixed    $data
+     * @param Schema[] $validSchemas
+     *
+     * @return self
+     */
+    public static function fromKeywordWithValidSchemas(
+        string $keyword,
+        $data,
+        array $validSchemas,
+        ?string $message = null
+    ) : KeywordMismatch {
+        $instance               = new self('Keyword validation failed: ' . $message, 0);
+        $instance->keyword      = $keyword;
+        $instance->data         = $data;
+        $instance->validSchemas = $validSchemas;
+
+        return $instance;
+    }
+
+    /**
+     * @return Schema[]
+     */
+    public function validSchemas() : array
+    {
+        return $this->validSchemas;
+    }
+}
diff --git a/src/Schema/Keywords/AnyOf.php b/src/Schema/Keywords/AnyOf.php
index 0d2b8888..c31183fc 100644
--- a/src/Schema/Keywords/AnyOf.php
+++ b/src/Schema/Keywords/AnyOf.php
@@ -8,6 +8,7 @@
 use League\OpenAPIValidation\Schema\BreadCrumb;
 use League\OpenAPIValidation\Schema\Exception\InvalidSchema;
 use League\OpenAPIValidation\Schema\Exception\KeywordMismatch;
+use League\OpenAPIValidation\Schema\Exception\NotEnoughValidSchemas;
 use League\OpenAPIValidation\Schema\Exception\SchemaMismatch;
 use League\OpenAPIValidation\Schema\SchemaValidator;
 use Respect\Validation\Exceptions\ExceptionInterface;
@@ -51,6 +52,8 @@ public function validate($data, array $anyOf) : void
             throw InvalidSchema::becauseDefensiveSchemaValidationFailed($e);
         }
 
+        $innerExceptions = [];
+
         foreach ($anyOf as $schema) {
             $schemaValidator = new SchemaValidator($this->validationDataType);
             try {
@@ -58,10 +61,15 @@ public function validate($data, array $anyOf) : void
 
                 return;
             } catch (SchemaMismatch $e) {
-                // that did not match... its ok
+                $innerExceptions[] = $e;
             }
         }
 
-        throw KeywordMismatch::fromKeyword('anyOf', $data, 'Data must match at least one schema');
+        throw NotEnoughValidSchemas::fromKeywordWithInnerExceptions(
+            'anyOf',
+            $data,
+            $innerExceptions,
+            'Data must match at least one schema'
+        );
     }
 }
diff --git a/src/Schema/Keywords/OneOf.php b/src/Schema/Keywords/OneOf.php
index 675185cd..99f46138 100644
--- a/src/Schema/Keywords/OneOf.php
+++ b/src/Schema/Keywords/OneOf.php
@@ -8,10 +8,13 @@
 use League\OpenAPIValidation\Schema\BreadCrumb;
 use League\OpenAPIValidation\Schema\Exception\InvalidSchema;
 use League\OpenAPIValidation\Schema\Exception\KeywordMismatch;
+use League\OpenAPIValidation\Schema\Exception\NotEnoughValidSchemas;
 use League\OpenAPIValidation\Schema\Exception\SchemaMismatch;
+use League\OpenAPIValidation\Schema\Exception\TooManyValidSchemas;
 use League\OpenAPIValidation\Schema\SchemaValidator;
 use Respect\Validation\Exceptions\ExceptionInterface;
 use Respect\Validation\Validator;
+use function count;
 use function sprintf;
 
 class OneOf extends BaseKeyword
@@ -53,19 +56,37 @@ public function validate($data, array $oneOf) : void
         }
 
         // Validate against all schemas
-        $matchedCount    = 0;
         $schemaValidator = new SchemaValidator($this->validationDataType);
+        $innerExceptions = [];
+        $validSchemas    = [];
+
         foreach ($oneOf as $schema) {
             try {
                 $schemaValidator->validate($data, $schema, $this->dataBreadCrumb);
-                $matchedCount++;
+                $validSchemas[] = $schema;
             } catch (SchemaMismatch $e) {
-                // that did not match... its ok
+                $innerExceptions[] = $e;
             }
         }
 
-        if ($matchedCount !== 1) {
-            throw KeywordMismatch::fromKeyword('oneOf', $data, sprintf('Data must match exactly one schema, but matched %d', $matchedCount));
+        if (count($validSchemas) === 1) {
+            return;
+        }
+
+        if (count($validSchemas) < 1) {
+            throw NotEnoughValidSchemas::fromKeywordWithInnerExceptions(
+                'oneOf',
+                $data,
+                $innerExceptions,
+                'Data must match exactly one schema, but matched none'
+            );
         }
+
+        throw TooManyValidSchemas::fromKeywordWithValidSchemas(
+            'oneOf',
+            $data,
+            $validSchemas,
+            sprintf('Data must match exactly one schema, but matched %d', count($validSchemas))
+        );
     }
 }