diff --git a/app/client/cypress/fixtures/testdata.json b/app/client/cypress/fixtures/testdata.json
index 107a8d24ad..e83cde0823 100644
--- a/app/client/cypress/fixtures/testdata.json
+++ b/app/client/cypress/fixtures/testdata.json
@@ -116,8 +116,8 @@
   "currentRowWithIdOutside": "#{{currentRow.email}}",
   "currentRowWithIdInside": "{{\"#\" + currentRow.email}}",
   "defaultdataBinding": "{'Test','This'}",
-  "dropdownErrorMsg": "This value does not evaluate to type \"Array<{ \"label\": \"string\", \"value\": \"string\" }>\".",
-  "tableWidgetErrorMsg": "This value does not evaluate to type \"Array<Object>\".",
+  "dropdownErrorMsg": "This value does not evaluate to type Array<{ \"label\": \"string\", \"value\": \"string\" }>",
+  "tableWidgetErrorMsg": "This value does not evaluate to type Array<Object>",
   "bindingDataPoint": "{{JSON.stringify(Chart1.selectedDataPoint)}}",
   "bindingSeriesTitle": "{{Chart1.selectedDataPoint.seriesTitle",
   "bindChartData": "{{Chart1.selectedDataPoint",
diff --git a/app/client/cypress/integration/Smoke_TestSuite/ClientSideTests/FormWidgets/DatePicker_2_spec.js b/app/client/cypress/integration/Smoke_TestSuite/ClientSideTests/FormWidgets/DatePicker_2_spec.js
index 39a28826e2..7513b7dfd6 100644
--- a/app/client/cypress/integration/Smoke_TestSuite/ClientSideTests/FormWidgets/DatePicker_2_spec.js
+++ b/app/client/cypress/integration/Smoke_TestSuite/ClientSideTests/FormWidgets/DatePicker_2_spec.js
@@ -61,9 +61,7 @@ describe("DatePicker Widget Property pane tests with js bindings", function() {
   it("Datepicker default date validation message", function() {
     cy.openPropertyPane("datepickerwidget2");
     cy.testJsontext("defaultdate", "24-12-2021");
-    cy.evaluateErrorMessage(
-      `This value does not evaluate to type "ISO 8601 date string".`,
-    );
+    cy.evaluateErrorMessage("Value does not match: ISO 8601 date string");
     cy.closePropertyPane();
   });
 
diff --git a/app/client/src/components/editorComponents/CodeEditor/EvaluatedValuePopup.tsx b/app/client/src/components/editorComponents/CodeEditor/EvaluatedValuePopup.tsx
index c52cb52ec5..6aeef4055d 100644
--- a/app/client/src/components/editorComponents/CodeEditor/EvaluatedValuePopup.tsx
+++ b/app/client/src/components/editorComponents/CodeEditor/EvaluatedValuePopup.tsx
@@ -21,10 +21,7 @@ import { IPopoverSharedProps } from "@blueprintjs/core";
 import { ReactComponent as CopyIcon } from "assets/icons/menu/copy-snippet.svg";
 import copy from "copy-to-clipboard";
 
-import {
-  EvaluationError,
-  PropertyEvaluationErrorType,
-} from "utils/DynamicBindingUtils";
+import { EvaluationError } from "utils/DynamicBindingUtils";
 import * as Sentry from "@sentry/react";
 import { Severity } from "@sentry/react";
 import { CodeEditorExpected } from "components/editorComponents/CodeEditor/index";
@@ -387,9 +384,9 @@ function PopoverContent(props: PopoverContentProps) {
       {hasError && error && (
         <ErrorText>
           <span className="t--evaluatedPopup-error">
-            {error.errorType === PropertyEvaluationErrorType.VALIDATION
-              ? `This value does not evaluate to type "${expected?.type}".`
-              : error.errorMessage}
+            {/* errorMessage could be an empty string */}
+            {error.errorMessage ||
+              `This value does not evaluate to type "${expected?.type}".`}
           </span>
           <EvaluatedValueDebugButton
             entity={props.entity}
diff --git a/app/client/src/constants/WidgetValidation.ts b/app/client/src/constants/WidgetValidation.ts
index bbd1dbe231..09258045e2 100644
--- a/app/client/src/constants/WidgetValidation.ts
+++ b/app/client/src/constants/WidgetValidation.ts
@@ -20,7 +20,7 @@ export enum ValidationTypes {
 export type ValidationResponse = {
   isValid: boolean;
   parsed: any;
-  message?: string;
+  messages?: string[];
   transformed?: any;
 };
 
diff --git a/app/client/src/sagas/EvaluationsSaga.ts b/app/client/src/sagas/EvaluationsSaga.ts
index 055d308d8e..cc855eb7fa 100644
--- a/app/client/src/sagas/EvaluationsSaga.ts
+++ b/app/client/src/sagas/EvaluationsSaga.ts
@@ -463,12 +463,14 @@ export function* evaluateArgumentSaga(action: any) {
     if (workerResponse.result) {
       const validation = validate({ type }, workerResponse.result, {});
       if (!validation.isValid)
-        lintErrors.unshift({
-          ...validation,
-          ...{
-            errorType: PropertyEvaluationErrorType.VALIDATION,
-            errorMessage: validation.message,
-          },
+        validation.messages?.map((message) => {
+          lintErrors.unshift({
+            ...validation,
+            ...{
+              errorType: PropertyEvaluationErrorType.VALIDATION,
+              errorMessage: message,
+            },
+          });
         });
     }
     yield put(
diff --git a/app/client/src/widgets/CheckboxGroupWidget/widget/index.tsx b/app/client/src/widgets/CheckboxGroupWidget/widget/index.tsx
index 858aebb755..b5bdc26e86 100644
--- a/app/client/src/widgets/CheckboxGroupWidget/widget/index.tsx
+++ b/app/client/src/widgets/CheckboxGroupWidget/widget/index.tsx
@@ -57,7 +57,7 @@ function defaultSelectedValuesValidation(
   return {
     isValid: false,
     parsed: values,
-    message: messages.join(" "),
+    messages,
   };
 }
 
diff --git a/app/client/src/widgets/DatePickerWidget/widget/index.tsx b/app/client/src/widgets/DatePickerWidget/widget/index.tsx
index d8454f4883..0f38289c27 100644
--- a/app/client/src/widgets/DatePickerWidget/widget/index.tsx
+++ b/app/client/src/widgets/DatePickerWidget/widget/index.tsx
@@ -24,14 +24,14 @@ function defaultDateValidation(
     return {
       isValid: true,
       parsed: "",
-      message: "",
+      messages: [""],
     };
   }
   if (value === undefined) {
     return {
       isValid: false,
       parsed: "",
-      message: `This value does not evaluate to type: Date ${dateFormat}`,
+      messages: [`This value does not evaluate to type: Date ${dateFormat}`],
     };
   }
 
@@ -40,10 +40,10 @@ function defaultDateValidation(
   return {
     isValid,
     parsed: isValid ? value : "",
-    message:
+    messages:
       isValid === false
-        ? `Value does not match ISO 8601 standard date string`
-        : "",
+        ? [`Value does not match ISO 8601 standard date string`]
+        : [""],
   };
 }
 
@@ -58,8 +58,9 @@ function minDateValidation(
     return {
       isValid: false,
       parsed: "",
-      message:
+      messages: [
         `Value does not match: Date String ` + (dateFormat ? dateFormat : ""),
+      ],
     };
   }
   const parsedMinDate = moment(value as string, dateFormat);
@@ -69,7 +70,7 @@ function minDateValidation(
     return {
       isValid: isValid,
       parsed: value,
-      message: "",
+      messages: [""],
     };
   }
   const parsedDefaultDate = moment(props.defaultDate, dateFormat);
@@ -85,14 +86,15 @@ function minDateValidation(
     return {
       isValid: isValid,
       parsed: "",
-      message:
+      messages: [
         `Value does not match: Date String ` + (dateFormat ? dateFormat : ""),
+      ],
     };
   }
   return {
     isValid: isValid,
     parsed: value,
-    message: "",
+    messages: [""],
   };
 }
 
@@ -107,9 +109,10 @@ function maxDateValidation(
     return {
       isValid: false,
       parsed: "",
-      message:
+      messages: [
         `Value does not match type: Date String ` +
-        (dateFormat ? dateFormat : ""),
+          (dateFormat ? dateFormat : ""),
+      ],
     };
   }
   const parsedMaxDate = moment(value as string, dateFormat);
@@ -118,7 +121,7 @@ function maxDateValidation(
     return {
       isValid: isValid,
       parsed: value,
-      message: "",
+      messages: [""],
     };
   }
   const parsedDefaultDate = moment(props.defaultDate, dateFormat);
@@ -134,15 +137,16 @@ function maxDateValidation(
     return {
       isValid: isValid,
       parsed: "",
-      message:
+      messages: [
         `Value does not match type: Date String ` +
-        (dateFormat ? dateFormat : ""),
+          (dateFormat ? dateFormat : ""),
+      ],
     };
   }
   return {
     isValid: isValid,
     parsed: value,
-    message: "",
+    messages: [""],
   };
 }
 class DatePickerWidget extends BaseWidget<DatePickerWidgetProps, WidgetState> {
diff --git a/app/client/src/widgets/DropdownWidget/widget/index.tsx b/app/client/src/widgets/DropdownWidget/widget/index.tsx
index 6f990ba734..4f945b38cc 100644
--- a/app/client/src/widgets/DropdownWidget/widget/index.tsx
+++ b/app/client/src/widgets/DropdownWidget/widget/index.tsx
@@ -18,7 +18,7 @@ function defaultOptionValueValidation(value: unknown): ValidationResponse {
     return {
       isValid: false,
       parsed: "",
-      message: "This value does not evaluate to type: string",
+      messages: ["This value does not evaluate to type: string"],
     };
   return { isValid: true, parsed: value };
 }
diff --git a/app/client/src/widgets/InputWidget/widget/index.test.tsx b/app/client/src/widgets/InputWidget/widget/index.test.tsx
index f2a92caf6d..777bcf544c 100644
--- a/app/client/src/widgets/InputWidget/widget/index.test.tsx
+++ b/app/client/src/widgets/InputWidget/widget/index.test.tsx
@@ -37,24 +37,24 @@ describe("#defaultValueValidation", () => {
     "abcd",
   ];
   const expectedOutputs = [
-    { isValid: true, parsed: undefined, message: "" },
-    { isValid: true, parsed: undefined, message: "" },
-    { isValid: true, parsed: 0, message: "" },
-    { isValid: true, parsed: 123, message: "" },
-    { isValid: true, parsed: -23, message: "" },
-    { isValid: true, parsed: 0.000001, message: "" },
-    { isValid: true, parsed: -23, message: "" },
-    { isValid: true, parsed: 0, message: "" },
-    { isValid: true, parsed: 100, message: "" },
+    { isValid: true, parsed: undefined, messages: [""] },
+    { isValid: true, parsed: undefined, messages: [""] },
+    { isValid: true, parsed: 0, messages: [""] },
+    { isValid: true, parsed: 123, messages: [""] },
+    { isValid: true, parsed: -23, messages: [""] },
+    { isValid: true, parsed: 0.000001, messages: [""] },
+    { isValid: true, parsed: -23, messages: [""] },
+    { isValid: true, parsed: 0, messages: [""] },
+    { isValid: true, parsed: 100, messages: [""] },
     {
       isValid: false,
       parsed: undefined,
-      message: "This value must be a number",
+      messages: ["This value must be a number"],
     },
     {
       isValid: false,
       parsed: undefined,
-      message: "This value must be a number",
+      messages: ["This value must be a number"],
     },
   ];
 
diff --git a/app/client/src/widgets/InputWidget/widget/index.tsx b/app/client/src/widgets/InputWidget/widget/index.tsx
index 21e965d7ef..74c2d5097d 100644
--- a/app/client/src/widgets/InputWidget/widget/index.tsx
+++ b/app/client/src/widgets/InputWidget/widget/index.tsx
@@ -43,7 +43,7 @@ export function defaultValueValidation(
         return {
           isValid: true,
           parsed: undefined,
-          message: "",
+          messages: [""],
         };
       }
 
@@ -51,7 +51,7 @@ export function defaultValueValidation(
         return {
           isValid: false,
           parsed: undefined,
-          message: "This value must be a number",
+          messages: ["This value must be a number"],
         };
       }
     }
@@ -59,14 +59,14 @@ export function defaultValueValidation(
     return {
       isValid: true,
       parsed,
-      message: "",
+      messages: [""],
     };
   }
   if (_.isObject(value)) {
     return {
       isValid: false,
       parsed: JSON.stringify(value, null, 2),
-      message: "This value must be string",
+      messages: ["This value must be string"],
     };
   }
   let parsed = value;
@@ -78,14 +78,14 @@ export function defaultValueValidation(
       return {
         isValid: false,
         parsed: "",
-        message: "This value must be string",
+        messages: ["This value must be string"],
       };
     }
   }
   return {
     isValid,
     parsed: parsed,
-    message: "",
+    messages: [""],
   };
 }
 
diff --git a/app/client/src/widgets/RateWidget/widget/index.tsx b/app/client/src/widgets/RateWidget/widget/index.tsx
index 823593faba..b245467320 100644
--- a/app/client/src/widgets/RateWidget/widget/index.tsx
+++ b/app/client/src/widgets/RateWidget/widget/index.tsx
@@ -29,7 +29,7 @@ function validateDefaultRate(value: unknown, props: any, _: any) {
         return {
           isValid: false,
           parsed: 0,
-          message: `Value must be a number`,
+          messages: [`Value must be a number`],
         };
       }
     }
@@ -43,7 +43,7 @@ function validateDefaultRate(value: unknown, props: any, _: any) {
       return {
         isValid: false,
         parsed,
-        message: `This value must be less than or equal to max count`,
+        messages: [`This value must be less than or equal to max count`],
       };
     }
 
@@ -52,7 +52,7 @@ function validateDefaultRate(value: unknown, props: any, _: any) {
       return {
         isValid: false,
         parsed,
-        message: `This value can be a decimal only if 'Allow half' is true`,
+        messages: [`This value can be a decimal only if 'Allow half' is true`],
       };
     }
 
@@ -61,7 +61,7 @@ function validateDefaultRate(value: unknown, props: any, _: any) {
     return {
       isValid: false,
       parsed: value,
-      message: `Could not validate `,
+      messages: [`Could not validate `],
     };
   }
 }
diff --git a/app/client/src/widgets/SingleSelectTreeWidget/widget/index.tsx b/app/client/src/widgets/SingleSelectTreeWidget/widget/index.tsx
index f137cabc5b..94e64ce807 100644
--- a/app/client/src/widgets/SingleSelectTreeWidget/widget/index.tsx
+++ b/app/client/src/widgets/SingleSelectTreeWidget/widget/index.tsx
@@ -21,7 +21,7 @@ function defaultOptionValueValidation(value: unknown): ValidationResponse {
     return {
       isValid: false,
       parsed: "",
-      message: "This value does not evaluate to type: string",
+      messages: ["This value does not evaluate to type: string"],
     };
   return { isValid: true, parsed: value };
 }
diff --git a/app/client/src/widgets/TabsWidget/widget/index.tsx b/app/client/src/widgets/TabsWidget/widget/index.tsx
index 307e2818c5..c699e73c29 100644
--- a/app/client/src/widgets/TabsWidget/widget/index.tsx
+++ b/app/client/src/widgets/TabsWidget/widget/index.tsx
@@ -25,7 +25,7 @@ export function selectedTabValidation(
   return {
     isValid: value === "" ? true : tabNames.includes(value as string),
     parsed: value,
-    message: `Tab name ${value} does not exist`,
+    messages: [`Tab name ${value} does not exist`],
   };
 }
 class TabsWidget extends BaseWidget<
diff --git a/app/client/src/workers/DataTreeEvaluator.ts b/app/client/src/workers/DataTreeEvaluator.ts
index 10ac6a4913..b2f7bcf6dc 100644
--- a/app/client/src/workers/DataTreeEvaluator.ts
+++ b/app/client/src/workers/DataTreeEvaluator.ts
@@ -2,6 +2,7 @@ import {
   DependencyMap,
   EvalError,
   EvalErrorTypes,
+  EvaluationError,
   getDynamicBindings,
   getEntityDynamicBindingPathList,
   getEvalErrorPath,
@@ -731,7 +732,7 @@ export default class DataTreeEvaluator {
     }
     const validation = widget.validationPaths[propertyPath];
 
-    const { isValid, message, parsed, transformed } = validateWidgetProperty(
+    const { isValid, messages, parsed, transformed } = validateWidgetProperty(
       validation,
       valueToValidate,
       widget,
@@ -749,18 +750,16 @@ export default class DataTreeEvaluator {
       safeEvaluatedValue,
     );
     if (!isValid) {
-      addErrorToEntityProperty(
-        [
-          {
+      const evalErrors: EvaluationError[] =
+        messages?.map((message) => {
+          return {
             raw: unEvalPropertyValue,
             errorMessage: message || "",
             errorType: PropertyEvaluationErrorType.VALIDATION,
             severity: Severity.ERROR,
-          },
-        ],
-        currentTree,
-        fullPropertyPath,
-      );
+          };
+        }) ?? [];
+      addErrorToEntityProperty(evalErrors, currentTree, fullPropertyPath);
     }
 
     if (isPathADynamicTrigger(widget, propertyPath)) {
diff --git a/app/client/src/workers/evaluationUtils.ts b/app/client/src/workers/evaluationUtils.ts
index 45b6a8fbfd..3fccb08c85 100644
--- a/app/client/src/workers/evaluationUtils.ts
+++ b/app/client/src/workers/evaluationUtils.ts
@@ -357,7 +357,7 @@ export function getValidatedTree(tree: DataTree) {
     Object.entries(entity.validationPaths).forEach(([property, validation]) => {
       const value = _.get(entity, property);
       // Pass it through parse
-      const { isValid, message, parsed, transformed } = validateWidgetProperty(
+      const { isValid, messages, parsed, transformed } = validateWidgetProperty(
         validation,
         value,
         entity,
@@ -375,15 +375,15 @@ export function getValidatedTree(tree: DataTree) {
         safeEvaluatedValue,
       );
       if (!isValid) {
+        const evalErrors: EvaluationError[] =
+          messages?.map((message) => ({
+            errorType: PropertyEvaluationErrorType.VALIDATION,
+            errorMessage: message,
+            severity: Severity.ERROR,
+            raw: value,
+          })) ?? [];
         addErrorToEntityProperty(
-          [
-            {
-              errorType: PropertyEvaluationErrorType.VALIDATION,
-              errorMessage: message || "",
-              severity: Severity.ERROR,
-              raw: value,
-            },
-          ],
+          evalErrors,
           tree,
           getEvalErrorPath(`${entityKey}.${property}`, false),
         );
diff --git a/app/client/src/workers/validations.test.ts b/app/client/src/workers/validations.test.ts
index 6c26978b24..27c90d851b 100644
--- a/app/client/src/workers/validations.test.ts
+++ b/app/client/src/workers/validations.test.ts
@@ -38,27 +38,35 @@ describe("Validate Validators", () => {
       {
         isValid: false,
         parsed: "abc",
-        message: "Value is not allowed",
+        messages: ["Value is not allowed"],
       },
       {
         isValid: false,
         parsed: "abc",
-        message: `${WIDGET_TYPE_VALIDATION_ERROR} string ( abc | 123 | mno | test )`,
+        messages: [
+          `${WIDGET_TYPE_VALIDATION_ERROR} string ( abc | 123 | mno | test )`,
+        ],
       },
       {
         isValid: false,
         parsed: "abc",
-        message: `${WIDGET_TYPE_VALIDATION_ERROR} string ( abc | 123 | mno | test )`,
+        messages: [
+          `${WIDGET_TYPE_VALIDATION_ERROR} string ( abc | 123 | mno | test )`,
+        ],
       },
       {
         isValid: false,
         parsed: "{}",
-        message: `${WIDGET_TYPE_VALIDATION_ERROR} string ( abc | 123 | mno | test )`,
+        messages: [
+          `${WIDGET_TYPE_VALIDATION_ERROR} string ( abc | 123 | mno | test )`,
+        ],
       },
       {
         isValid: false,
         parsed: "[]",
-        message: `${WIDGET_TYPE_VALIDATION_ERROR} string ( abc | 123 | mno | test )`,
+        messages: [
+          `${WIDGET_TYPE_VALIDATION_ERROR} string ( abc | 123 | mno | test )`,
+        ],
       },
       {
         isValid: true,
@@ -115,12 +123,14 @@ describe("Validate Validators", () => {
       {
         isValid: false,
         parsed: "abc",
-        message: "Value is not allowed",
+        messages: ["Value is not allowed"],
       },
       {
         isValid: false,
         parsed: "abc",
-        message: `${WIDGET_TYPE_VALIDATION_ERROR} string ( abc | 123 | mno | test )`,
+        messages: [
+          `${WIDGET_TYPE_VALIDATION_ERROR} string ( abc | 123 | mno | test )`,
+        ],
       },
     ];
     inputs.forEach((input, index) => {
@@ -166,7 +176,9 @@ describe("Validate Validators", () => {
         isValid: false,
         parsed:
           "https://cdn.dribbble.com/users/1787323/screenshots/4563995/dribbbe_hammer-01.png",
-        message: `${WIDGET_TYPE_VALIDATION_ERROR}: base64 encoded image | data uri | image url`,
+        messages: [
+          `${WIDGET_TYPE_VALIDATION_ERROR}: base64 encoded image | data uri | image url`,
+        ],
       },
     ];
 
@@ -195,27 +207,31 @@ describe("Validate Validators", () => {
       {
         isValid: false,
         parsed: 90,
-        message: "Minimum allowed value: 100",
+        messages: ["Minimum allowed value: 100"],
       },
       {
         isValid: false,
         parsed: 220,
-        message: "Maximum allowed value: 200",
+        messages: ["Maximum allowed value: 200"],
       },
       {
         isValid: false,
         parsed: 150,
-        message: "This value is required",
+        messages: ["This value is required"],
       },
       {
         isValid: false,
         parsed: 150,
-        message: `${WIDGET_TYPE_VALIDATION_ERROR} number Min: 100 Max: 200 Required`,
+        messages: [
+          `${WIDGET_TYPE_VALIDATION_ERROR} number Min: 100 Max: 200 Required`,
+        ],
       },
       {
         isValid: false,
         parsed: 150,
-        message: `${WIDGET_TYPE_VALIDATION_ERROR} number Min: 100 Max: 200 Required`,
+        messages: [
+          `${WIDGET_TYPE_VALIDATION_ERROR} number Min: 100 Max: 200 Required`,
+        ],
       },
       {
         isValid: true,
@@ -224,7 +240,7 @@ describe("Validate Validators", () => {
       {
         isValid: false,
         parsed: 150,
-        message: "This value is required",
+        messages: ["This value is required"],
       },
     ];
     inputs.forEach((input, index) => {
@@ -267,12 +283,12 @@ describe("Validate Validators", () => {
     const expected = [
       {
         isValid: false,
-        message: `${WIDGET_TYPE_VALIDATION_ERROR} boolean`,
+        messages: [`${WIDGET_TYPE_VALIDATION_ERROR} boolean`],
         parsed: false,
       },
       {
         isValid: false,
-        message: `${WIDGET_TYPE_VALIDATION_ERROR} boolean`,
+        messages: [`${WIDGET_TYPE_VALIDATION_ERROR} boolean`],
         parsed: false,
       },
       {
@@ -285,12 +301,12 @@ describe("Validate Validators", () => {
       },
       {
         isValid: false,
-        message: `${WIDGET_TYPE_VALIDATION_ERROR} boolean`,
+        messages: [`${WIDGET_TYPE_VALIDATION_ERROR} boolean`],
         parsed: false,
       },
       {
         isValid: false,
-        message: `${WIDGET_TYPE_VALIDATION_ERROR} boolean`,
+        messages: [`${WIDGET_TYPE_VALIDATION_ERROR} boolean`],
         parsed: false,
       },
       {
@@ -304,7 +320,7 @@ describe("Validate Validators", () => {
       {
         isValid: false,
         parsed: false,
-        message: "This value does not evaluate to type boolean",
+        messages: ["This value does not evaluate to type boolean"],
       },
     ];
 
@@ -388,27 +404,35 @@ describe("Validate Validators", () => {
       {
         isValid: false,
         parsed: { key1: 120, key2: "abc" },
-        message: `${WIDGET_TYPE_VALIDATION_ERROR}: { \"key1\": \"number Required\", \"key2\": \"string ( abc | mnop )\" }`,
+        messages: [
+          `${WIDGET_TYPE_VALIDATION_ERROR}: { \"key1\": \"number Required\", \"key2\": \"string ( abc | mnop )\" }`,
+        ],
       },
       {
         isValid: false,
         parsed: { key1: 120, key2: "abc" },
-        message: `${WIDGET_TYPE_VALIDATION_ERROR}: { \"key1\": \"number Required\", \"key2\": \"string ( abc | mnop )\" }`,
+        messages: [
+          `${WIDGET_TYPE_VALIDATION_ERROR}: { \"key1\": \"number Required\", \"key2\": \"string ( abc | mnop )\" }`,
+        ],
       },
       {
         isValid: false,
         parsed: { key1: 120, key2: "abc" },
-        message: `Value of key: key1 is invalid: This value does not evaluate to type number Required`,
+        messages: [
+          `Value of key: key1 is invalid: This value does not evaluate to type number Required`,
+        ],
       },
       {
         isValid: false,
         parsed: { key1: 120, key2: "abc" },
-        message: `Value of key: key2 is invalid: This value does not evaluate to type string ( abc | mnop )`,
+        messages: [
+          `Value of key: key2 is invalid: This value does not evaluate to type string ( abc | mnop )`,
+        ],
       },
       {
         isValid: false,
         parsed: { key1: 120, key2: "abc" },
-        message: `Missing required key: key1`,
+        messages: [`Missing required key: key1`],
       },
     ];
     inputs.forEach((input, index) => {
@@ -451,73 +475,79 @@ describe("Validate Validators", () => {
       {
         isValid: true,
         parsed: ["a", "b", "c"],
-        message: "",
+        messages: [],
       },
       {
         isValid: true,
         parsed: ["m", "n", "b"],
-        message: "",
+        messages: [],
       },
       {
         isValid: false,
         parsed: [],
-        message: "Invalid entry at index: 2. Value is not allowed",
+        messages: ["Invalid entry at index: 2. Value is not allowed"],
       },
       {
         isValid: true,
         parsed: [],
-        message: "",
+        messages: [],
       },
       {
         isValid: false,
         parsed: [],
-        message:
+        messages: [
           "This value does not evaluate to type Array<string ( a | b | c | n | m | p | r )>",
+        ],
       },
       {
         isValid: false,
         parsed: [],
-        message:
+        messages: [
           "This property is required for the widget to function correctly",
+        ],
       },
       {
         isValid: false,
         parsed: [],
-        message:
+        messages: [
           "This property is required for the widget to function correctly",
+        ],
       },
       {
         isValid: false,
         parsed: [],
-        message:
+        messages: [
           "This value does not evaluate to type Array<string ( a | b | c | n | m | p | r )>",
+        ],
       },
       {
         isValid: true,
         parsed: ["a", "b", "c"],
-        message: "",
+        messages: [],
       },
       {
         isValid: false,
         parsed: [],
-        message:
+        messages: [
           "This value does not evaluate to type Array<string ( a | b | c | n | m | p | r )>",
+        ],
       },
       {
         isValid: false,
         parsed: [],
-        message: "Array must be unique. Duplicate values found",
+        messages: ["Array must be unique. Duplicate values found"],
       },
       {
         isValid: false,
         parsed: [],
-        message:
+        messages: [
           "This property is required for the widget to function correctly",
+        ],
       },
       {
         isValid: true,
         parsed: [],
-        message: "",
+        messages: [],
       },
     ];
     inputs.forEach((input, index) => {
@@ -594,39 +624,44 @@ describe("Validate Validators", () => {
       {
         isValid: true,
         parsed: [{ label: 123, value: 234 }],
-        message: "",
+        messages: [],
       },
       {
         isValid: true,
         parsed: [{ label: 123, value: 234 }],
-        message: "",
+        messages: [],
       },
       {
         isValid: false,
         parsed: [],
-        message: "Invalid entry at index: 0. Missing required key: label",
+        messages: ["Invalid entry at index: 0. Missing required key: label"],
       },
       {
         isValid: false,
         parsed: [],
-        message: `Invalid entry at index: 0. Value of key: label is invalid: This value does not evaluate to type number Required`,
+        messages: [
+          `Invalid entry at index: 0. Value of key: label is invalid: This value does not evaluate to type number Required`,
+        ],
       },
       {
         isValid: false,
         parsed: [],
-        message:
-          "Invalid entry at index: 0. Missing required key: label Missing required key: value",
+        messages: [
+          "Invalid entry at index: 0. Missing required key: label",
+          "Invalid entry at index: 0. Missing required key: value",
+        ],
       },
       {
         isValid: true,
         parsed: [],
-        message: "",
+        messages: [],
       },
       {
         isValid: false,
         parsed: [],
-        message:
+        messages: [
           "This property is required for the widget to function correctly",
+        ],
       },
     ];
     inputs.forEach((input, index) => {
@@ -711,16 +746,16 @@ describe("Validate Validators", () => {
       {
         isValid: false,
         parsed: defaultDate,
-        message: "Value does not match: ISO 8601 date string",
+        messages: ["Value does not match: ISO 8601 date string"],
       },
       {
         isValid: false,
         parsed: defaultDate,
-        message: "Value does not match: ISO 8601 date string",
+        messages: ["Value does not match: ISO 8601 date string"],
       },
       {
         isValid: false,
-        message: "Value does not match: ISO 8601 date string",
+        messages: ["Value does not match: ISO 8601 date string"],
         parsed: defaultDate,
       },
     ];
@@ -800,52 +835,52 @@ describe("Validate Validators", () => {
       {
         isValid: false,
         parsed: [{ id: 1, name: "alpha" }],
-        message: "This value does not evaluate to type Array<Object>",
+        messages: ["This value does not evaluate to type Array<Object>"],
       },
       {
         isValid: false,
         parsed: [{ id: 1, name: "alpha" }],
-        message: "This value does not evaluate to type Array<Object>",
+        messages: ["This value does not evaluate to type Array<Object>"],
       },
       {
         isValid: false,
         parsed: [{ id: 1, name: "alpha" }],
-        message: "This value does not evaluate to type Array<Object>",
+        messages: ["This value does not evaluate to type Array<Object>"],
       },
       {
         isValid: false,
         parsed: [{ id: 1, name: "alpha" }],
-        message: "This value does not evaluate to type Array<Object>",
+        messages: ["This value does not evaluate to type Array<Object>"],
       },
       {
         isValid: false,
         parsed: [{ id: 1, name: "alpha" }],
-        message: "This value does not evaluate to type Array<Object>",
+        messages: ["This value does not evaluate to type Array<Object>"],
       },
       {
         isValid: false,
         parsed: [{ id: 1, name: "alpha" }],
-        message: "This value does not evaluate to type Array<Object>",
+        messages: ["This value does not evaluate to type Array<Object>"],
       },
       {
         isValid: false,
         parsed: [{ id: 1, name: "alpha" }],
-        message: "Invalid object at index 0",
+        messages: ["Invalid object at index 0"],
       },
       {
         isValid: false,
         parsed: [{ id: 1, name: "alpha" }],
-        message: "Invalid object at index 1",
+        messages: ["Invalid object at index 1"],
       },
       {
         isValid: false,
         parsed: [{ id: 1, name: "alpha" }],
-        message: "Invalid object at index 1",
+        messages: ["Invalid object at index 1"],
       },
       {
         isValid: false,
         parsed: [{ id: 1, name: "alpha" }],
-        message: "This value does not evaluate to type Array<Object>",
+        messages: ["This value does not evaluate to type Array<Object>"],
       },
     ];
 
@@ -928,12 +963,12 @@ describe("Validate Validators", () => {
       },
       {
         isValid: false,
-        message: `${WIDGET_TYPE_VALIDATION_ERROR}: URL`,
+        messages: [`${WIDGET_TYPE_VALIDATION_ERROR}: URL`],
         parsed: "https://wikipedia.org",
       },
       {
         isValid: false,
-        message: `${WIDGET_TYPE_VALIDATION_ERROR}: URL`,
+        messages: [`${WIDGET_TYPE_VALIDATION_ERROR}: URL`],
         parsed: "https://wikipedia.org",
       },
     ];
diff --git a/app/client/src/workers/validations.ts b/app/client/src/workers/validations.ts
index 9a7ef08732..e882650b26 100644
--- a/app/client/src/workers/validations.ts
+++ b/app/client/src/workers/validations.ts
@@ -59,7 +59,7 @@ function validatePlainObject(
       const entryName = getPropertyEntry(value, entry.name, ignoreCase);
 
       if (value.hasOwnProperty(entryName)) {
-        const { isValid, message, parsed } = validate(
+        const { isValid, messages, parsed } = validate(
           entry,
           value[entryName],
           props,
@@ -67,8 +67,12 @@ function validatePlainObject(
         if (!isValid) {
           value[entryName] = parsed;
           _valid = isValid;
-          message &&
-            _messages.push(`Value of key: ${entryName} is invalid: ${message}`);
+          messages &&
+            messages.map((message) => {
+              _messages.push(
+                `Value of key: ${entryName} is invalid: ${message}`,
+              );
+            });
         }
       } else if (entry.params?.required) {
         _valid = false;
@@ -84,7 +88,7 @@ function validatePlainObject(
     return {
       isValid: false,
       parsed: config.params?.default || value,
-      message: _messages.join(" "),
+      messages: _messages,
     };
   }
   return {
@@ -107,7 +111,7 @@ function validateArray(
         return {
           isValid: false,
           parsed: value,
-          message: `Disallowed value: ${entry}`,
+          messages: [`Disallowed value: ${entry}`],
         };
       }
     });
@@ -170,8 +174,8 @@ function validateArray(
       const validation = validate(children, entry, props);
       if (!validation.isValid) {
         _isValid = false;
-        _messages.push(
-          `Invalid entry at index: ${index}. ${validation.message}`,
+        validation.messages?.map((message) =>
+          _messages.push(`Invalid entry at index: ${index}. ${message}`),
         );
       }
     });
@@ -185,7 +189,7 @@ function validateArray(
         if (uniq(shouldBeUnique).length !== value.length) {
           _isValid = false;
           _messages.push(
-            `Array entry path:${param} must be unique. Duplicate values found`,
+            `path:${param} must be unique. Duplicate values found`,
           );
           break;
         }
@@ -201,7 +205,7 @@ function validateArray(
   return {
     isValid: _isValid,
     parsed: _isValid ? value : config.params?.default || [],
-    message: _messages.join(" "),
+    messages: _messages,
   };
 }
 
@@ -296,7 +300,9 @@ export const VALIDATORS: Record<ValidationTypes, Validator> = {
         return {
           isValid: false,
           parsed: config.params?.default || "",
-          message: `${WIDGET_TYPE_VALIDATION_ERROR} ${getExpectedType(config)}`,
+          messages: [
+            `${WIDGET_TYPE_VALIDATION_ERROR} ${getExpectedType(config)}`,
+          ],
         };
       }
 
@@ -311,7 +317,9 @@ export const VALIDATORS: Record<ValidationTypes, Validator> = {
       return {
         isValid: false,
         parsed: JSON.stringify(value, null, 2),
-        message: `${WIDGET_TYPE_VALIDATION_ERROR} ${getExpectedType(config)}`,
+        messages: [
+          `${WIDGET_TYPE_VALIDATION_ERROR} ${getExpectedType(config)}`,
+        ],
       };
     }
 
@@ -319,7 +327,7 @@ export const VALIDATORS: Record<ValidationTypes, Validator> = {
     const stringValidationError = {
       isValid: false,
       parsed: config.params?.default || "",
-      message: `${WIDGET_TYPE_VALIDATION_ERROR} ${getExpectedType(config)}`,
+      messages: [`${WIDGET_TYPE_VALIDATION_ERROR} ${getExpectedType(config)}`],
     };
     if (!isValid) {
       try {
@@ -335,7 +343,7 @@ export const VALIDATORS: Record<ValidationTypes, Validator> = {
       if (!config.params?.allowedValues.includes((parsed as string).trim())) {
         return {
           parsed: config.params?.default || "",
-          message: "Value is not allowed",
+          messages: ["Value is not allowed"],
           isValid: false,
         };
       }
@@ -348,7 +356,9 @@ export const VALIDATORS: Record<ValidationTypes, Validator> = {
     ) {
       return {
         parsed: config.params?.default || "",
-        message: `Value does not match expected regex: ${config.params?.regex.source}`,
+        messages: [
+          `Value does not match expected regex: ${config.params?.regex.source}`,
+        ],
         isValid: false,
       };
     }
@@ -364,7 +374,7 @@ export const VALIDATORS: Record<ValidationTypes, Validator> = {
     value: unknown,
     props: Record<string, unknown>,
   ): ValidationResponse => {
-    const { isValid, message, parsed } = VALIDATORS[ValidationTypes.TEXT](
+    const { isValid, messages, parsed } = VALIDATORS[ValidationTypes.TEXT](
       config,
       value,
       props,
@@ -374,11 +384,13 @@ export const VALIDATORS: Record<ValidationTypes, Validator> = {
       return {
         isValid: false,
         parsed: new RegExp(parsed),
-        message: `${WIDGET_TYPE_VALIDATION_ERROR} ${getExpectedType(config)}`,
+        messages: [
+          `${WIDGET_TYPE_VALIDATION_ERROR} ${getExpectedType(config)}`,
+        ],
       };
     }
 
-    return { isValid, parsed, message };
+    return { isValid, parsed, messages };
   },
   [ValidationTypes.NUMBER]: (
     config: ValidationConfig,
@@ -390,7 +402,7 @@ export const VALIDATORS: Record<ValidationTypes, Validator> = {
         return {
           isValid: false,
           parsed: config.params?.default || 0,
-          message: "This value is required",
+          messages: ["This value is required"],
         };
       }
 
@@ -410,7 +422,9 @@ export const VALIDATORS: Record<ValidationTypes, Validator> = {
       return {
         isValid: false,
         parsed: config.params?.default || 0,
-        message: `${WIDGET_TYPE_VALIDATION_ERROR} ${getExpectedType(config)}`,
+        messages: [
+          `${WIDGET_TYPE_VALIDATION_ERROR} ${getExpectedType(config)}`,
+        ],
       };
     }
 
@@ -423,7 +437,9 @@ export const VALIDATORS: Record<ValidationTypes, Validator> = {
         return {
           isValid: false,
           parsed: config.params?.default || 0,
-          message: `${WIDGET_TYPE_VALIDATION_ERROR} ${getExpectedType(config)}`,
+          messages: [
+            `${WIDGET_TYPE_VALIDATION_ERROR} ${getExpectedType(config)}`,
+          ],
         };
       }
     }
@@ -436,7 +452,7 @@ export const VALIDATORS: Record<ValidationTypes, Validator> = {
         return {
           isValid: false,
           parsed,
-          message: `Minimum allowed value: ${config.params.min}`,
+          messages: [`Minimum allowed value: ${config.params.min}`],
         };
       }
     }
@@ -449,7 +465,7 @@ export const VALIDATORS: Record<ValidationTypes, Validator> = {
         return {
           isValid: false,
           parsed,
-          message: `Maximum allowed value: ${config.params.max}`,
+          messages: [`Maximum allowed value: ${config.params.max}`],
         };
       }
     }
@@ -457,7 +473,7 @@ export const VALIDATORS: Record<ValidationTypes, Validator> = {
       return {
         isValid: false,
         parsed,
-        message: `Value should be a positive integer`,
+        messages: [`Value should be a positive integer`],
       };
     }
 
@@ -476,7 +492,9 @@ export const VALIDATORS: Record<ValidationTypes, Validator> = {
         return {
           isValid: false,
           parsed: !!config.params?.default,
-          message: `${WIDGET_TYPE_VALIDATION_ERROR} ${getExpectedType(config)}`,
+          messages: [
+            `${WIDGET_TYPE_VALIDATION_ERROR} ${getExpectedType(config)}`,
+          ],
         };
       }
 
@@ -500,7 +518,9 @@ export const VALIDATORS: Record<ValidationTypes, Validator> = {
       return {
         isValid: false,
         parsed: config.params?.default || false,
-        message: `${WIDGET_TYPE_VALIDATION_ERROR} ${getExpectedType(config)}`,
+        messages: [
+          `${WIDGET_TYPE_VALIDATION_ERROR} ${getExpectedType(config)}`,
+        ],
       };
     }
 
@@ -520,9 +540,9 @@ export const VALIDATORS: Record<ValidationTypes, Validator> = {
         return {
           isValid: false,
           parsed: config.params?.default || {},
-          message: `${WIDGET_TYPE_VALIDATION_ERROR}: ${getExpectedType(
-            config,
-          )}`,
+          messages: [
+            `${WIDGET_TYPE_VALIDATION_ERROR}: ${getExpectedType(config)}`,
+          ],
         };
       }
       return {
@@ -547,13 +567,17 @@ export const VALIDATORS: Record<ValidationTypes, Validator> = {
       return {
         isValid: false,
         parsed: config.params?.default || {},
-        message: `${WIDGET_TYPE_VALIDATION_ERROR}: ${getExpectedType(config)}`,
+        messages: [
+          `${WIDGET_TYPE_VALIDATION_ERROR}: ${getExpectedType(config)}`,
+        ],
       };
     } catch (e) {
       return {
         isValid: false,
         parsed: config.params?.default || {},
-        message: `${WIDGET_TYPE_VALIDATION_ERROR}: ${getExpectedType(config)}`,
+        messages: [
+          `${WIDGET_TYPE_VALIDATION_ERROR}: ${getExpectedType(config)}`,
+        ],
       };
     }
   },
@@ -565,7 +589,7 @@ export const VALIDATORS: Record<ValidationTypes, Validator> = {
     const invalidResponse = {
       isValid: false,
       parsed: config.params?.default || [],
-      message: `${WIDGET_TYPE_VALIDATION_ERROR} ${getExpectedType(config)}`,
+      messages: [`${WIDGET_TYPE_VALIDATION_ERROR} ${getExpectedType(config)}`],
     };
     if (value === undefined || value === null || value === "") {
       if (
@@ -573,8 +597,9 @@ export const VALIDATORS: Record<ValidationTypes, Validator> = {
         config.params.required &&
         !isArray(config.params.default)
       ) {
-        invalidResponse.message =
-          "This property is required for the widget to function correctly";
+        invalidResponse.messages = [
+          "This property is required for the widget to function correctly",
+        ];
         return invalidResponse;
       }
       if (value === "") {
@@ -622,7 +647,7 @@ export const VALIDATORS: Record<ValidationTypes, Validator> = {
     const invalidResponse = {
       isValid: false,
       parsed: config.params?.default || [{}],
-      message: `${WIDGET_TYPE_VALIDATION_ERROR} ${getExpectedType(config)}`,
+      messages: [`${WIDGET_TYPE_VALIDATION_ERROR} ${getExpectedType(config)}`],
     };
     if (value === undefined || value === null || value === "") {
       if (config.params?.required) return invalidResponse;
@@ -666,7 +691,7 @@ export const VALIDATORS: Record<ValidationTypes, Validator> = {
         if (!isPlainObject(parsedEntry)) {
           return {
             ...invalidResponse,
-            message: `Invalid object at index ${index}`,
+            messages: [`Invalid object at index ${index}`],
           };
         }
       }
@@ -683,7 +708,7 @@ export const VALIDATORS: Record<ValidationTypes, Validator> = {
     let response: ValidationResponse = {
       isValid: false,
       parsed: config.params?.default || [],
-      message: `${WIDGET_TYPE_VALIDATION_ERROR} ${getExpectedType(config)}`,
+      messages: [`${WIDGET_TYPE_VALIDATION_ERROR} ${getExpectedType(config)}`],
     };
     response = VALIDATORS.ARRAY(config, value, props);
 
@@ -702,7 +727,9 @@ export const VALIDATORS: Record<ValidationTypes, Validator> = {
             response = {
               ...response,
               isValid: false,
-              message: `Array entry path:${param} must be unique. Duplicate values found`,
+              messages: [
+                `path:${param} must be unique. Duplicate values found`,
+              ],
             };
           }
         }
@@ -718,7 +745,7 @@ export const VALIDATORS: Record<ValidationTypes, Validator> = {
     const invalidResponse = {
       isValid: false,
       parsed: config.params?.default || moment().toISOString(true),
-      message: `Value does not match: ${getExpectedType(config)}`,
+      messages: [`Value does not match: ${getExpectedType(config)}`],
     };
     if (value === undefined || value === null || !isString(value)) {
       if (!config.params?.required) {
@@ -761,7 +788,7 @@ export const VALIDATORS: Record<ValidationTypes, Validator> = {
     const invalidResponse = {
       isValid: false,
       parsed: undefined,
-      message: "Failed to validate",
+      messages: ["Failed to validate"],
     };
     if (config.params?.fnString && isString(config.params?.fnString)) {
       try {
@@ -786,7 +813,7 @@ export const VALIDATORS: Record<ValidationTypes, Validator> = {
     const invalidResponse = {
       isValid: false,
       parsed: config.params?.default || "",
-      message: `${WIDGET_TYPE_VALIDATION_ERROR}: ${getExpectedType(config)}`,
+      messages: [`${WIDGET_TYPE_VALIDATION_ERROR}: ${getExpectedType(config)}`],
     };
     const base64Regex = /^(?:[A-Za-z\d+\/]{4})*?(?:[A-Za-z\d+\/]{2}(?:==)?|[A-Za-z\d+\/]{3}=?)?$/;
     const base64ImageRegex = /^data:image\/.*;base64/;
@@ -822,7 +849,7 @@ export const VALIDATORS: Record<ValidationTypes, Validator> = {
     const invalidResponse = {
       isValid: false,
       parsed: config?.params?.default || "",
-      message: `${WIDGET_TYPE_VALIDATION_ERROR}: ${getExpectedType(config)}`,
+      messages: [`${WIDGET_TYPE_VALIDATION_ERROR}: ${getExpectedType(config)}`],
     };
 
     if (typeof value === "string" && getIsSafeURL(value)) {