diff --git a/app/client/cypress/e2e/Regression/ClientSide/Widgets/Filepicker/FilePicker3_spec.ts b/app/client/cypress/e2e/Regression/ClientSide/Widgets/Filepicker/FilePicker3_spec.ts
new file mode 100644
index 0000000000..95dd2280df
--- /dev/null
+++ b/app/client/cypress/e2e/Regression/ClientSide/Widgets/Filepicker/FilePicker3_spec.ts
@@ -0,0 +1,218 @@
+import {
+  agHelper,
+  locators,
+  entityExplorer,
+  deployMode,
+  propPane,
+} from "../../../../../support/Objects/ObjectsCore";
+
+describe("Verify file picker widget", () => {
+  before(() => {
+    agHelper.AddDsl("filepickerDsl");
+  });
+  it("1. Verify property visibility", () => {
+    const basicProperties = [
+      "allowedfiletypes",
+      "dataformat",
+      `maxno\\.offiles`,
+    ];
+
+    const labelProperties = ["text"];
+
+    const validationProperties = ["required", "maxfilesize\\(mb\\)"];
+
+    const generalProperties = ["visible", "disable", "animateloading"];
+
+    const eventsProperties = ["onfilesselected"];
+
+    const styleColorProperties = ["buttoncolor"];
+
+    const styleBorderProperties = ["borderradius", "boxshadow"];
+
+    entityExplorer.SelectEntityByName("FilePicker1", "Widgets");
+
+    propPane.AssertPropertyVisibility(basicProperties, "basic");
+    propPane.AssertPropertyVisibility(labelProperties, "label");
+    propPane.AssertPropertyVisibility(validationProperties, "validation");
+    propPane.AssertPropertyVisibility(generalProperties, "general");
+    propPane.AssertPropertyVisibility(eventsProperties, "events");
+    propPane.MoveToTab("Style");
+    propPane.AssertPropertyVisibility(styleColorProperties, "color");
+    propPane.AssertPropertyVisibility(styleBorderProperties, "borderandshadow");
+  });
+
+  it("2. Verify Renaming, duplication and deletion", () => {
+    // Rename and verify
+    entityExplorer.RenameEntityFromExplorer(
+      "FilePicker1",
+      "NewFilePicker",
+      true,
+    );
+    agHelper.AssertElementVisibility(locators._widgetName("NewFilePicker"));
+
+    // Copy and paste widget using cmd+c and cmd+v
+    entityExplorer.CopyPasteWidget("NewFilePicker");
+    entityExplorer.AssertEntityPresenceInExplorer("NewFilePickerCopy");
+    entityExplorer.DeleteWidgetFromEntityExplorer("NewFilePickerCopy");
+
+    // Copy paste from property pane and delete from property pane
+    propPane.CopyPasteWidgetFromPropertyPane("NewFilePicker");
+    propPane.DeleteWidgetFromPropertyPane("NewFilePickerCopy");
+    entityExplorer.SelectEntityByName("NewFilePicker", "Widgets");
+    propPane.MoveToTab("Content");
+  });
+
+  it("3. Verify max number of files", () => {
+    agHelper.AssertText(locators._buttonText, "text", "Select Files");
+    propPane.UpdatePropertyFieldValue("Max no. of files", "2");
+    agHelper.ClickButton("Select Files");
+    agHelper.UploadFile("AAAFlowerVase.jpeg");
+    // Verify Add more is visible
+    agHelper.GetNClick(locators._buttonInDeployedMode, 0, true);
+    agHelper.AssertElementVisibility(locators._fileUploadAddMore);
+    agHelper.GetNClick(locators._fileUploadAddMore);
+
+    // Verify Add more does not exist when max no. files are added
+    agHelper.UploadFile("appsmithlogo.png");
+    agHelper.GetNClick(locators._buttonInDeployedMode, 0, true);
+    agHelper.AssertElementAbsence(locators._fileUploadAddMore);
+    agHelper.GetNClick(locators._fileUploadDashboardClose);
+
+    agHelper.AssertText(locators._buttonText, "text", "2 files selected");
+  });
+
+  it("4. Verify Validation max file size supported", () => {
+    propPane.UpdatePropertyFieldValue("Max file size(Mb)", "1");
+    agHelper.GetNClick(locators._buttonInDeployedMode, 0, true);
+    agHelper.GetNClick('[title="Remove file"]');
+    agHelper.GetNClick(locators._fileUploadAddMore);
+    agHelper
+      .GetElement(locators._uploadFiles)
+      .eq(0)
+      .selectFile("cypress/fixtures/Appsmith.gif", { force: true })
+      .wait(3000);
+    agHelper.AssertElementVisibility(
+      locators._fileUploadErrorContains(
+        "This file exceeds maximum allowed size of 1 MB ",
+      ),
+    );
+    agHelper.GetNClick(locators._fileUploadDashboardClose);
+  });
+
+  it("5. Validate visible and disabled toggle", () => {
+    propPane.TogglePropertyState("visible", "Off");
+
+    // Preview mode
+    agHelper.GetNClick(locators._enterPreviewMode);
+    agHelper.AssertElementAbsence(
+      locators._widgetInDeployed("filepickerwidgetv2"),
+    );
+    agHelper.GetNClick(locators._exitPreviewMode);
+
+    // Deploy mode
+    deployMode.DeployApp();
+    agHelper.AssertElementAbsence(
+      locators._widgetInDeployed("filepickerwidgetv2"),
+    );
+    deployMode.NavigateBacktoEditor();
+
+    entityExplorer.SelectEntityByName("NewFilePicker", "Widgets");
+    propPane.TogglePropertyState("visible", "On");
+
+    // Preview mode
+    agHelper.GetNClick(locators._enterPreviewMode);
+    agHelper.AssertElementVisibility(
+      locators._widgetInDeployed("filepickerwidgetv2"),
+    );
+    agHelper.GetNClick(locators._exitPreviewMode);
+
+    // Deploy mode
+    deployMode.DeployApp();
+    agHelper.AssertElementVisibility(
+      locators._widgetInDeployed("filepickerwidgetv2"),
+    );
+    deployMode.NavigateBacktoEditor();
+
+    // Visible JS mode
+    entityExplorer.SelectEntityByName("NewFilePicker", "Widgets");
+    propPane.ToggleJSMode("Visible", true);
+    propPane.UpdatePropertyFieldValue("Visible", "false");
+
+    deployMode.DeployApp();
+    agHelper.AssertElementAbsence(
+      locators._widgetInDeployed("filepickerwidgetv2"),
+    );
+    deployMode.NavigateBacktoEditor();
+
+    entityExplorer.SelectEntityByName("NewFilePicker", "Widgets");
+    propPane.ToggleJSMode("Visible", true);
+    propPane.UpdatePropertyFieldValue("Visible", "true");
+    propPane.ToggleJSMode("Visible", false);
+
+    // Disabled
+    propPane.TogglePropertyState("disable", "On");
+    agHelper.AssertAttribute(
+      locators._widgetInDeployed("filepickerwidgetv2"),
+      "disabled",
+      "disabled",
+    );
+
+    // Preview mode
+    agHelper.GetNClick(locators._enterPreviewMode);
+    agHelper.AssertAttribute(
+      locators._widgetInDeployed("filepickerwidgetv2"),
+      "disabled",
+      "disabled",
+    );
+    agHelper.GetNClick(locators._exitPreviewMode);
+
+    // Deploy mode
+    deployMode.DeployApp();
+    agHelper.AssertAttribute(
+      locators._widgetInDeployed("filepickerwidgetv2"),
+      "disabled",
+      "disabled",
+    );
+    deployMode.NavigateBacktoEditor();
+
+    entityExplorer.SelectEntityByName("NewFilePicker", "Widgets");
+    propPane.TogglePropertyState("disable", "Off");
+  });
+
+  it("6. Verify onFilesSelected", () => {
+    propPane.ToggleJSMode("onFilesSelected", true);
+    propPane.UpdatePropertyFieldValue(
+      "onFilesSelected",
+      "{{showAlert('File Selected', '');}}",
+    );
+    deployMode.DeployApp();
+    agHelper.ClickButton("Select Files");
+    agHelper.UploadFile("appsmithlogo.png");
+    agHelper.ValidateToastMessage("File Selected");
+    deployMode.NavigateBacktoEditor();
+  });
+
+  it("7. Verify button color and border and shadows", () => {
+    entityExplorer.SelectEntityByName("NewFilePicker", "Widgets");
+    // Verify button color picker opens up
+    propPane.MoveToTab("Style");
+    agHelper.GetNClick(propPane._propertyControlColorPicker("buttoncolor"));
+    agHelper.AssertElementVisibility(propPane._colorPickerV2Color);
+    // Verify full color picker
+    agHelper.AssertAttribute(propPane._colorPickerInput, "type", "text", 0);
+    propPane.TogglePropertyState("buttoncolor", "On", "");
+    agHelper.AssertAttribute(propPane._colorPickerInput, "type", "color", 0);
+
+    // Verify border
+    agHelper.GetNClick(propPane._segmentedControl("0px"));
+    agHelper.AssertCSS(locators._buttonInDeployedMode, "border-radius", "0px");
+
+    // Verify Box Shadow
+    agHelper.GetNClick(`${propPane._segmentedControl("0")}:contains('Large')`);
+    agHelper.AssertCSS(
+      locators._buttonInDeployedMode,
+      "box-shadow",
+      "rgba(0, 0, 0, 0.1) 0px 10px 15px -3px, rgba(0, 0, 0, 0.05) 0px 4px 6px -2px",
+    );
+  });
+});
diff --git a/app/client/cypress/fixtures/Appsmith.gif b/app/client/cypress/fixtures/Appsmith.gif
new file mode 100644
index 0000000000..53c281cd21
Binary files /dev/null and b/app/client/cypress/fixtures/Appsmith.gif differ
diff --git a/app/client/cypress/support/Objects/CommonLocators.ts b/app/client/cypress/support/Objects/CommonLocators.ts
index 8f939196e0..8879ba216c 100644
--- a/app/client/cypress/support/Objects/CommonLocators.ts
+++ b/app/client/cypress/support/Objects/CommonLocators.ts
@@ -302,4 +302,9 @@ export class CommonLocators {
   _callbackAddBtn = ".action-callback-add .ads-v2-button";
   _checkboxInDeployedMode = "//label[contains(@class, 'bp3-checkbox')]//input";
   _listText = "//span[text()='Blue']/../..";
+  _fileUploadDashboardClose = ".uppy-Dashboard-close";
+  _fileUploadErrorContains = (msg: string) =>
+    `.uppy-Informer p:contains('${msg}')`;
+  _fileUploadAddMore = ".uppy-DashboardContent-addMore";
+  _buttonText = ".bp3-button-text";
 }