diff --git a/src/Controls/tests/TestCases.HostApp/Issues/Issue30957.cs b/src/Controls/tests/TestCases.HostApp/Issues/Issue30957.cs
new file mode 100644
index 000000000000..a3d4f4d58fb3
--- /dev/null
+++ b/src/Controls/tests/TestCases.HostApp/Issues/Issue30957.cs
@@ -0,0 +1,126 @@
+using Microsoft.Maui.Layouts;
+
+namespace Maui.Controls.Sample.Issues
+{
+    [Issue(IssueTracker.Github, 30957, "FlexLayout Wrap Misalignment with Dynamically-Sized Buttons in .NET MAUI", PlatformAffected.All)]
+    public class Issue30957 : ContentPage
+    {
+        FlexLayout _testFlexLayout;
+        Label _statusLabel;
+        Button _toggleButton1, _toggleButton2, _toggleButton3;
+        bool _isToggled = false;
+
+        public Issue30957()
+        {
+            Title = "Issue30957";
+
+            var stackLayout = new StackLayout { Padding = new Thickness(20) };
+
+            var instructionsLabel = new Label
+            {
+                AutomationId = "Issue30957FirstLabel",
+                Text = "This reproduces FlexLayout wrapping issue with font family switching. Click 'Toggle Font' to trigger precision issues.",
+                Margin = new Thickness(0, 0, 0, 20)
+            };
+            stackLayout.Children.Add(instructionsLabel);
+
+            var toggleAllButton = new Button
+            {
+                Text = "Toggle Font Family",
+                AutomationId = "Issue30957ToggleButton",
+                BackgroundColor = Colors.LightBlue,
+                Margin = new Thickness(0, 0, 0, 10)
+            };
+            toggleAllButton.Clicked += OnToggleFontClicked;
+            stackLayout.Children.Add(toggleAllButton);
+
+            var border = new Border
+            {
+                Stroke = Colors.Black,
+                StrokeThickness = 1,
+                BackgroundColor = Colors.White,
+                HorizontalOptions = LayoutOptions.Start,
+                Padding = new Thickness(4)
+            };
+
+            _testFlexLayout = new FlexLayout
+            {
+                Wrap = FlexWrap.Wrap
+            };
+
+            _toggleButton1 = new Button
+            {
+                Text = "Button1",
+                AutomationId = "Issue30957Button1",
+                BackgroundColor = Colors.White,
+                FontFamily = "OpenSansRegular",
+                CornerRadius = 0,
+                FontSize = 16,
+                TextColor = Colors.Black
+            };
+
+            _toggleButton2 = new Button
+            {
+                Text = "Button2",
+                AutomationId = "Issue30957Button2",
+                BackgroundColor = Colors.White,
+                FontFamily = "OpenSansRegular",
+                CornerRadius = 0,
+                FontSize = 16,
+                TextColor = Colors.Black
+            };
+
+            _toggleButton3 = new Button
+            {
+                Text = "Button3",
+                AutomationId = "Issue30957Button3",
+                BackgroundColor = Colors.White,
+                FontFamily = "OpenSansRegular",
+                CornerRadius = 0,
+                FontSize = 16,
+                TextColor = Colors.Black
+            };
+
+            _testFlexLayout.Children.Add(_toggleButton1);
+            _testFlexLayout.Children.Add(_toggleButton2);
+            _testFlexLayout.Children.Add(_toggleButton3);
+
+            border.Content = _testFlexLayout;
+            stackLayout.Children.Add(border);
+
+            _statusLabel = new Label
+            {
+                AutomationId = "Issue30957StatusLabel",
+                Text = "Status: Ready to test - Click 'Toggle Font Family' to trigger precision issue",
+                Margin = new Thickness(0, 10, 0, 0),
+                TextColor = Colors.DarkGreen
+            };
+            stackLayout.Children.Add(_statusLabel);
+
+            Content = stackLayout;
+        }
+
+        void OnToggleFontClicked(object sender, EventArgs e)
+        {
+            _isToggled = !_isToggled;
+
+            string fontFamily = _isToggled ? "OpenSansSemibold" : "OpenSansRegular";
+            Color backgroundColor = _isToggled ? Colors.Black : Colors.White;
+            Color textColor = _isToggled ? Colors.White : Colors.Black;
+
+            _toggleButton1.FontFamily = fontFamily;
+            _toggleButton1.BackgroundColor = backgroundColor;
+            _toggleButton1.TextColor = textColor;
+
+            _toggleButton2.FontFamily = fontFamily;
+            _toggleButton2.BackgroundColor = backgroundColor;
+            _toggleButton2.TextColor = textColor;
+
+            _toggleButton3.FontFamily = fontFamily;
+            _toggleButton3.BackgroundColor = backgroundColor;
+            _toggleButton3.TextColor = textColor;
+
+            _statusLabel.Text = $"Status: Font toggled to {fontFamily} - This triggers precision issue that tolerance fix addresses";
+        }
+    }
+}
diff --git a/src/Controls/tests/TestCases.Shared.Tests/Tests/Issues/Issue30957.cs b/src/Controls/tests/TestCases.Shared.Tests/Tests/Issues/Issue30957.cs
new file mode 100644
index 000000000000..c3582cc5ce3c
--- /dev/null
+++ b/src/Controls/tests/TestCases.Shared.Tests/Tests/Issues/Issue30957.cs
@@ -0,0 +1,35 @@
+using NUnit.Framework;
+using UITest.Appium;
+using UITest.Core;
+
+namespace Microsoft.Maui.TestCases.Tests.Issues
+{
+	public class Issue30957 : _IssuesUITest
+	{
+		public Issue30957(TestDevice testDevice) : base(testDevice)
+		{
+		}
+
+		public override string Issue => "FlexLayout Wrap Misalignment with Dynamically-Sized Buttons in .NET MAUI";
+
+		[Test]
+		[Category(UITestCategories.Layout)]
+		public void FlexLayoutWrappingWithToleranceWorksCorrectly()
+		{
+			App.WaitForElement("Issue30957ToggleButton");
+			App.Tap("Issue30957ToggleButton");
+
+			var button1Rect = App.WaitForElement("Issue30957Button1").GetRect();
+			var button2Rect = App.WaitForElement("Issue30957Button2").GetRect();
+			var button3Rect = App.WaitForElement("Issue30957Button3").GetRect();
+
+			// All three buttons should be on the same row (same Y position)
+			Assert.That(button2Rect.Y, Is.EqualTo(button1Rect.Y), "Button1 and Button2 should have the same Y position (same row)");
+			Assert.That(button3Rect.Y, Is.EqualTo(button1Rect.Y), "Button1 and Button3 should have the same Y position (same row)");
+
+			// Buttons should be laid out horizontally: each subsequent button starts after the previous one
+			Assert.That(button2Rect.X, Is.GreaterThan(button1Rect.X), "Button2 should be to the right of Button1");
+			Assert.That(button3Rect.X, Is.GreaterThan(button2Rect.X), "Button3 should be to the right of Button2");
+		}
+	}
+}
diff --git a/src/Core/src/Layouts/Flex.cs b/src/Core/src/Layouts/Flex.cs
index 2ecadeccf1af..31f4d1557777 100644
--- a/src/Core/src/Layouts/Flex.cs
+++ b/src/Core/src/Layouts/Flex.cs
@@ -533,10 +533,29 @@ static void layout_item(Item item, float width, float height, bool inMeasureMode
 					child.Frame[layout.frame_size_i] = basis - child.MarginThickness(layout.vertical);
 				}
 
+#if ANDROID || WINDOWS
+				// A small tolerance value used to account for floating-point precision errors
+				// when determining whether a child item fits on the current line during flex wrapping.
+				// Without this tolerance, items that should fit may be incorrectly wrapped to a new line
+				// due to minor rounding discrepancies in size calculations.
+				// 0.1f accounts for sub-pixel rounding errors introduced by DPI scaling factors
+				// (e.g., 1.25x on Windows, 2.625x density on Android). Values below 1.0f have
+				// no meaningful effect on intentional layout gaps which are always >= 1dp.
+				const float FlexWrapTolerance = 0.1f;
+
+				// The issue was originally reported on Windows, related to device density or
+				// scaling factor. It has also been reproduced on Android due to density variations.
+				// The tolerance is applied unconditionally across all platforms as a conservative fix;
+				// it has no adverse effects on layout behavior.
+				float flex_tolerance = layout.flex_dim + FlexWrapTolerance;
+#else
+				// On other platforms, we haven't observed the same precision issues, so we can use the actual available space as the tolerance.
+				float flex_tolerance = layout.flex_dim;
+#endif
 				float child_size = child.Frame[layout.frame_size_i];
 				if (layout.wrap)
 				{
-					if (layout.flex_dim < child_size)
+					if (flex_tolerance < child_size)
 					{
 						// Not enough space for this child on this line, layout the
 						// remaining items and move it to a new line.