diff --git a/packages/main/cypress/specs/DynamicDateRange.cy.tsx b/packages/main/cypress/specs/DynamicDateRange.cy.tsx
index 47974c128fa3..f3c90c5f075f 100644
--- a/packages/main/cypress/specs/DynamicDateRange.cy.tsx
+++ b/packages/main/cypress/specs/DynamicDateRange.cy.tsx
@@ -75,36 +75,122 @@ describe('DynamicDateRange Component', () => {
         cy.get("@input").should('have.value', 'Today');
     });
 
-    // Unstable test, needs investigation
-    it.skip('selects the Date option and updates the current value', () => {
-        cy.window().then((win) => {
-            cy.stub(win.Date, 'now').returns(new Date(2025, 4, 15).getTime());
-          });
 
-        cy.get('[ui5-dynamic-date-range]').as("ddr");
-        cy.get("@ddr").shadow().find('[ui5-input]').as("input");
+    it('selects the Date option and updates the current value', () => {
+        cy.get('[ui5-dynamic-date-range]')
+            .as("ddr");
+
+        cy.get("@ddr")
+            .shadow()
+            .find('[ui5-input]')
+            .as("input");
     
-        cy.get("@input").should('exist');
+        cy.get("@input")
+            .should('exist');
     
-        cy.get("@input").find('[ui5-icon]').as("icon");
-        cy.get("@icon").realClick();
-    
-        cy.get("@ddr").shadow().find("[ui5-responsive-popover]").as("popover");
-        cy.get("@popover").should('exist');
+        cy.get("@input")
+            .find('[ui5-icon]')
+            .as("icon");
 
-        cy.get("@popover").find("[ui5-list]").as("list");
-        cy.get("@list").find("[ui5-li]").contains('Date').realClick();
+        cy.get("@icon")
+            .realClick();
     
-        cy.get("@popover").find("[ui5-calendar]").as("calendar");
-        cy.get("@calendar").should('exist');
+        cy.get("@ddr")
+            .shadow()
+            .find("[ui5-responsive-popover]")
+            .as("popover");
+
+        cy.get("@popover")
+            .should('exist');
+
+        cy.get("@popover")
+            .find("[ui5-list]")
+            .as("list");
+
+        cy.get("@list")
+            .find("[ui5-li]")
+            .contains('Date')
+            .realClick();
     
-        cy.get("@calendar").shadow().find("ui5-daypicker").as("dayPicker");
-        cy.get("@dayPicker").shadow().find("div[data-sap-timestamp='1747785600']").realClick();
+        cy.get("@popover")
+            .find("[ui5-calendar]")
+            .as("calendar");
 
-        cy.get("@popover").find("[ui5-button][design='Emphasized']").as("submitButton");
-        cy.get("@submitButton").should('exist').realClick();
+        cy.get("@calendar")
+            .should('exist');
 
-        cy.get("@input").shadow().find("input").should('have.value', 'May 21, 2025');
+        cy.realPress("Tab");
+        cy.realPress("Tab");
+        cy.realPress("Tab");
+        
+        cy.get("@calendar")
+            .shadow()
+            .find("[data-ui5-cal-header-btn-year='true']")
+            .as("yearButton");
+
+        cy.get("@yearButton")
+            .should("be.focused");
+        
+        cy.realPress("Space");
+        
+        cy.get("@calendar")
+            .shadow()
+            .find("ui5-yearpicker")
+            .as("yearPicker");
+
+        cy.get("@yearPicker")
+            .shadow()
+            .find(".ui5-dp-yeartext")
+            .contains('2035')
+            .realClick();
+
+        cy.realPress("Tab");
+        cy.realPress("Tab");
+        
+        cy.get("@calendar")
+            .shadow()
+            .find("[data-ui5-cal-header-btn-month='true']")
+            .as("monthButton");
+
+        cy.get("@monthButton")
+            .should("be.focused");
+
+        cy.realPress("Space");
+
+        cy.get("@calendar")
+            .shadow()
+            .find("ui5-monthpicker")
+            .as("monthPicker");
+
+        cy.get("@monthPicker")
+            .shadow()
+            .find(".ui5-dp-monthtext")
+            .contains('May')
+            .realClick();
+
+        cy.get("@calendar")
+            .shadow()
+            .find("ui5-daypicker")
+            .as("dayPicker");
+
+        cy.get("@dayPicker")
+            .shadow()
+            .find(".ui5-dp-daytext")
+            .eq(22) // May 21, 2035 is the 21st day
+            .realClick();
+
+        cy.get("@popover")
+            .find("[ui5-button][design='Emphasized']")
+            .as("submitButton");
+
+        cy.get("@submitButton")
+            .should('exist')
+            .realClick();
+
+        cy.get("@input")
+            .shadow()
+            .find("input")
+            .should('have.value', 'May 21, 2035');
     });
 
     it('writes a date in the input and verifies it is selected in the calendar for the Date option', () => {