diff --git a/src/decorator/string/Length.ts b/src/decorator/string/Length.ts
index 04427bdfb..db2d2956d 100644
--- a/src/decorator/string/Length.ts
+++ b/src/decorator/string/Length.ts
@@ -12,6 +12,32 @@ export function length(value: unknown, min: number, max?: number): boolean {
   return typeof value === 'string' && isLengthValidator(value, { min, max });
 }
 
+/**
+ * Character length used to choose the default Length message.
+ * With `{ each: true }`, `args.value` is the whole collection, so collection.size would pick the wrong bound.
+ */
+function characterLengthForMessage(value: unknown, min: number, max?: number): number | undefined {
+  if (typeof value === 'string') {
+    return value.length;
+  }
+
+  let items: unknown[] | undefined;
+  if (Array.isArray(value)) {
+    items = value;
+  } else if (value instanceof Set) {
+    items = Array.from(value);
+  } else if (value instanceof Map) {
+    items = Array.from(value.values());
+  }
+
+  if (items) {
+    const failing = items.find(item => typeof item === 'string' && !length(item, min, max));
+    return typeof failing === 'string' ? failing.length : undefined;
+  }
+
+  return value != null ? (value as { length?: number }).length : undefined;
+}
+
 /**
  * Checks if the string's length falls in a range. Note: this function takes into account surrogate pairs.
  * If given value is not a string, then it returns false.
@@ -24,11 +50,15 @@ export function Length(min: number, max?: number, validationOptions?: Validation
       validator: {
         validate: (value, args): boolean => length(value, args?.constraints[0], args?.constraints[1]),
         defaultMessage: buildMessage((eachPrefix, args) => {
-          const isMinLength = args?.constraints[0] !== null && args?.constraints[0] !== undefined;
-          const isMaxLength = args?.constraints[1] !== null && args?.constraints[1] !== undefined;
-          if (isMinLength && (!args.value || args.value.length < args?.constraints[0])) {
+          const min = args?.constraints[0];
+          const max = args?.constraints[1];
+          const isMinLength = min !== null && min !== undefined;
+          const isMaxLength = max !== null && max !== undefined;
+          const charLength = characterLengthForMessage(args?.value, min, max);
+
+          if (isMinLength && (charLength === undefined || charLength < min)) {
             return eachPrefix + '$property must be longer than or equal to $constraint1 characters';
-          } else if (isMaxLength && args.value.length > args?.constraints[1]) {
+          } else if (isMaxLength && charLength !== undefined && charLength > max) {
             return eachPrefix + '$property must be shorter than or equal to $constraint2 characters';
           }
           return (
diff --git a/test/functional/validation-functions-and-decorators.spec.ts b/test/functional/validation-functions-and-decorators.spec.ts
index 4c266f02e..fa9e7c34d 100644
--- a/test/functional/validation-functions-and-decorators.spec.ts
+++ b/test/functional/validation-functions-and-decorators.spec.ts
@@ -4267,6 +4267,33 @@ describe('Length', () => {
     const message = 'someProperty must be shorter than or equal to ' + constraintToString(constraint2) + ' characters';
     return checkReturnedError(new MyClass(), ['aaaa', 'azzazza'], validationType, message);
   });
+
+  describe('with each: true', () => {
+    class TagsClass {
+      @Length(constraint1, constraint2, { each: true })
+      someProperty: string[];
+    }
+
+    it('should not fail for valid items', () => {
+      return checkValidValues(new TagsClass(), [['ab', 'abc'], ['de']]);
+    });
+
+    it('should report max-length when an item is too long', () => {
+      const validationType = 'isLength';
+      const message =
+        'each value in someProperty must be shorter than or equal to ' +
+        constraintToString(constraint2) +
+        ' characters';
+      return checkReturnedError(new TagsClass(), [['abcd'], ['aaaa']], validationType, message);
+    });
+
+    it('should report min-length when items are too short', () => {
+      const validationType = 'isLength';
+      const message =
+        'each value in someProperty must be longer than or equal to ' + constraintToString(constraint1) + ' characters';
+      return checkReturnedError(new TagsClass(), [['a', 'a', 'a', 'a']], validationType, message);
+    });
+  });
 });
 
 describe('MinLength', () => {