diff --git a/yup/src/__tests__/__fixtures__/data.ts b/yup/src/__tests__/__fixtures__/data.ts
index 9499b94a..a6a04aa0 100644
--- a/yup/src/__tests__/__fixtures__/data.ts
+++ b/yup/src/__tests__/__fixtures__/data.ts
@@ -5,8 +5,15 @@ export const schema = yup.object({
   username: yup.string().matches(/^\w+$/).min(3).max(30).required(),
   password: yup
     .string()
-    .matches(/^[a-zA-Z0-9]{3,30}/)
-    .required(),
+    .matches(new RegExp('.*[A-Z].*'), 'One uppercase character')
+    .matches(new RegExp('.*[a-z].*'), 'One lowercase character')
+    .matches(new RegExp('.*\\d.*'), 'One number')
+    .matches(
+      new RegExp('.*[`~<>?,./!@#$%^&*()\\-_+="\'|{}\\[\\];:\\\\].*'),
+      'One special character',
+    )
+    .min(8, 'Must be at least 8 characters in length')
+    .required('New Password is required'),
   repeatPassword: yup.ref('password'),
   accessToken: yup.string(),
   birthYear: yup.number().min(1900).max(2013),
@@ -23,8 +30,8 @@ export const schema = yup.object({
 
 export const validData: yup.InferType<typeof schema> = {
   username: 'Doe',
-  password: 'Password123',
-  repeatPassword: 'Password123',
+  password: 'Password123_',
+  repeatPassword: 'Password123_',
   birthYear: 2000,
   email: 'john@doe.com',
   tags: ['tag1', 'tag2'],
diff --git a/yup/src/__tests__/__snapshots__/yup.ts.snap b/yup/src/__tests__/__snapshots__/yup.ts.snap
index 2b44967a..012d39ab 100644
--- a/yup/src/__tests__/__snapshots__/yup.ts.snap
+++ b/yup/src/__tests__/__snapshots__/yup.ts.snap
@@ -23,7 +23,7 @@ Object {
       },
     ],
     "password": Object {
-      "message": "password must match the following: \\"/^[a-zA-Z0-9]{3,30}/\\"",
+      "message": "One uppercase character",
       "ref": Object {
         "name": "password",
       },
@@ -64,7 +64,7 @@ Object {
       },
     ],
     "password": Object {
-      "message": "password must match the following: \\"/^[a-zA-Z0-9]{3,30}/\\"",
+      "message": "One uppercase character",
       "ref": Object {
         "name": "password",
       },
@@ -114,13 +114,18 @@ Object {
       },
     ],
     "password": Object {
-      "message": "password must match the following: \\"/^[a-zA-Z0-9]{3,30}/\\"",
+      "message": "One uppercase character",
       "ref": Object {
         "name": "password",
       },
       "type": "matches",
       "types": Object {
-        "matches": "password must match the following: \\"/^[a-zA-Z0-9]{3,30}/\\"",
+        "matches": Array [
+          "One uppercase character",
+          "One lowercase character",
+          "One number",
+        ],
+        "min": "Must be at least 8 characters in length",
       },
     },
     "username": Object {
@@ -170,13 +175,18 @@ Object {
       },
     ],
     "password": Object {
-      "message": "password must match the following: \\"/^[a-zA-Z0-9]{3,30}/\\"",
+      "message": "One uppercase character",
       "ref": Object {
         "name": "password",
       },
       "type": "matches",
       "types": Object {
-        "matches": "password must match the following: \\"/^[a-zA-Z0-9]{3,30}/\\"",
+        "matches": Array [
+          "One uppercase character",
+          "One lowercase character",
+          "One number",
+        ],
+        "min": "Must be at least 8 characters in length",
       },
     },
     "username": Object {
diff --git a/yup/src/yup.ts b/yup/src/yup.ts
index 65bd82c6..0de99d4e 100644
--- a/yup/src/yup.ts
+++ b/yup/src/yup.ts
@@ -17,12 +17,17 @@ const parseErrorSchema = (
     }
 
     if (validateAllFieldCriteria) {
+      const types = previous[error.path!].types;
+      const messages = types && types[error.type!];
+
       previous[error.path!] = appendErrors(
         error.path!,
         validateAllFieldCriteria,
         previous,
         error.type!,
-        error.message,
+        messages
+          ? ([] as string[]).concat(messages as string[], error.message)
+          : error.message,
       ) as FieldError;
     }