diff --git a/samples/Sentry.Samples.Maui/MainPage.xaml.cs b/samples/Sentry.Samples.Maui/MainPage.xaml.cs
index b82a13787d..9ea62da935 100644
--- a/samples/Sentry.Samples.Maui/MainPage.xaml.cs
+++ b/samples/Sentry.Samples.Maui/MainPage.xaml.cs
@@ -1,3 +1,4 @@
+using System.Globalization;
 using Microsoft.Extensions.Logging;
 
 namespace Sentry.Samples.Maui;
diff --git a/samples/Sentry.Samples.Maui/MauiProgram.cs b/samples/Sentry.Samples.Maui/MauiProgram.cs
index c1789d3850..e95f0fd986 100644
--- a/samples/Sentry.Samples.Maui/MauiProgram.cs
+++ b/samples/Sentry.Samples.Maui/MauiProgram.cs
@@ -61,6 +61,11 @@ public static MauiApp CreateMauiApp()
                 // sentry:SessionReplay.Mask="Unmask" attribute to individual controls instead.
                 options.Native.ExperimentalOptions.SessionReplay.UnmaskControlsOfType<Button>();
 #endif
+#if __IOS__ || __MACCATALYST__
+                // SDK users must explicitly opt-in to Session Replay in unreliable environments - when running liquid
+                // glass on iOS 26.0 or later
+                options.Native.ExperimentalOptions.SessionReplay.EnableSessionReplayInUnreliableEnvironment = true;
+#endif
 #endif
 
                 options.SetBeforeScreenshotCapture((@event, hint) =>
diff --git a/src/Sentry/Platforms/Cocoa/Extensions/BreadcrumbExtensions.cs b/src/Sentry/Platforms/Cocoa/Extensions/BreadcrumbExtensions.cs
index c87bce2559..f9594947f8 100644
--- a/src/Sentry/Platforms/Cocoa/Extensions/BreadcrumbExtensions.cs
+++ b/src/Sentry/Platforms/Cocoa/Extensions/BreadcrumbExtensions.cs
@@ -19,7 +19,7 @@ public static CocoaSdk.SentryBreadcrumb ToCocoaBreadcrumb(this Breadcrumb breadc
             Timestamp = breadcrumb.Timestamp.ToNSDate(),
             Message = breadcrumb.Message,
             Type = breadcrumb.Type,
-            Data = breadcrumb.Data?.ToNullableNSDictionary(),
+            Data = breadcrumb.Data?.ToCocoaBreadcrumbData(),
             Category = breadcrumb.Category ?? "",
             Level = breadcrumb.Level.ToCocoaSentryLevel()
         };
diff --git a/src/Sentry/Platforms/Cocoa/Extensions/CocoaExtensions.cs b/src/Sentry/Platforms/Cocoa/Extensions/CocoaExtensions.cs
index cf6776a450..00c91e5d75 100644
--- a/src/Sentry/Platforms/Cocoa/Extensions/CocoaExtensions.cs
+++ b/src/Sentry/Platforms/Cocoa/Extensions/CocoaExtensions.cs
@@ -195,6 +195,39 @@ public static NSDictionary<NSString, NSString> ToNSDictionaryStrings(
         this IReadOnlyCollection<KeyValuePair<string, TValue>> dict) =>
         dict.Count == 0 ? null : dict.ToNSDictionary();
 
+    public static NSDictionary<NSString, NSObject>? ToCocoaBreadcrumbData(
+        this IReadOnlyDictionary<string, string> source)
+    {
+        // Avoid an allocation if we can
+        if (source.Count == 0)
+        {
+            return null;
+        }
+
+        var dict = new Dictionary<NSString, NSObject>();
+
+        foreach (var (key, value) in source)
+        {
+            // Cocoa Session Replay expects `request_start` to be a Date (`NSDate`).
+            // See https://github.com/getsentry/sentry-cocoa/blob/2b4e787e55558e1475eda8f98b02c19a0d511741/Sources/Swift/Integrations/SessionReplay/SentrySRDefaultBreadcrumbConverter.swift#L73
+            if (key == SentryHttpMessageHandler.RequestStartKey && TryParseUnixMs(value, out var unixMs))
+            {
+                var dto = DateTimeOffset.FromUnixTimeMilliseconds(unixMs);
+                dict[(NSString)key] = dto.ToNSDate();
+                continue;
+            }
+
+            dict[(NSString)key] = NSObject.FromObject(value);
+        }
+
+        return dict.Count == 0
+            ? null
+            : NSDictionary<NSString, NSObject>.FromObjectsAndKeys(dict.Values.ToArray(), dict.Keys.ToArray());
+
+        static bool TryParseUnixMs(string value, out long unixMs) =>
+            long.TryParse(value, NumberStyles.Integer, CultureInfo.InvariantCulture, out unixMs);
+    }
+
     /// <summary>
     /// Converts an <see cref="NSNumber"/> to a .NET primitive data type and returns the result box in an <see cref="object"/>.
     /// </summary>
diff --git a/src/Sentry/SentryHttpMessageHandler.cs b/src/Sentry/SentryHttpMessageHandler.cs
index 6f8489690d..c2aca78cdf 100644
--- a/src/Sentry/SentryHttpMessageHandler.cs
+++ b/src/Sentry/SentryHttpMessageHandler.cs
@@ -17,6 +17,7 @@ public class SentryHttpMessageHandler : SentryMessageHandler
     internal const string HttpClientOrigin = "auto.http.client";
     internal const string HttpStartTimestampKey = "http.start_timestamp";
     internal const string HttpEndTimestampKey = "http.end_timestamp";
+    internal const string RequestStartKey = "request_start";
 
     /// <summary>
     /// Constructs an instance of <see cref="SentryHttpMessageHandler"/>.
@@ -91,15 +92,19 @@ protected internal override void HandleResponse(HttpResponseMessage response, IS
             {"method", method},
             {"status_code", ((int) response.StatusCode).ToString()}
         };
-#if ANDROID
         if (span is not null)
         {
+#if ANDROID
             // Ensure the breadcrumb can be converted to RRWeb so that it shows up in the network tab in Session Replay.
             // See https://github.com/getsentry/sentry-java/blob/94bff8dc0a952ad8c1b6815a9eda5005e41b92c7/sentry-android-replay/src/main/java/io/sentry/android/replay/DefaultReplayBreadcrumbConverter.kt#L195-L199
             breadcrumbData[HttpStartTimestampKey] = span.StartTimestamp.ToUnixTimeMilliseconds().ToString("F0", CultureInfo.InvariantCulture);
             breadcrumbData[HttpEndTimestampKey] = DateTimeOffset.UtcNow.ToUnixTimeMilliseconds().ToString("F0", CultureInfo.InvariantCulture);
-        }
+#elif IOS || MACCATALYST
+            // Ensure the breadcrumb can be converted to RRWeb so that it shows up in the network tab in Session Replay.
+            // See https://github.com/getsentry/sentry-cocoa/blob/2b4e787e55558e1475eda8f98b02c19a0d511741/Sources/Swift/Integrations/SessionReplay/SentrySRDefaultBreadcrumbConverter.swift#L70-L86
+            breadcrumbData[RequestStartKey] = span.StartTimestamp.ToUnixTimeMilliseconds().ToString("F0", CultureInfo.InvariantCulture);
 #endif
+        }
         _hub.AddBreadcrumb(string.Empty, "http", "http", breadcrumbData);
 
         // Create events for failed requests
diff --git a/test/Sentry.Tests/Platforms/iOS/CocoaExtensionsTests.cs b/test/Sentry.Tests/Platforms/iOS/CocoaExtensionsTests.cs
index 04e782e639..2a7fdd97f1 100644
--- a/test/Sentry.Tests/Platforms/iOS/CocoaExtensionsTests.cs
+++ b/test/Sentry.Tests/Platforms/iOS/CocoaExtensionsTests.cs
@@ -1,5 +1,6 @@
 using System;
 using System.Collections.Generic;
+using System.Globalization;
 using System.Linq;
 using FluentAssertions;
 using Foundation;
@@ -78,6 +79,63 @@ public void ToSentryEvent_ConvertToManaged()
         AssertEqual(managed, native);
     }
 
+    [Fact]
+    public void ToCocoaBreadcrumbData_EmptyDictionary_ReturnsNull()
+    {
+        var source = new Dictionary<string, string>();
+        var result = source.ToCocoaBreadcrumbData();
+        result.Should().BeNull();
+    }
+
+    [Fact]
+    public void ToCocoaBreadcrumbData_RegularKeys_ConvertsToNSObject()
+    {
+        var source = new Dictionary<string, string>
+        {
+            { "url", "https://example.com" },
+            { "method", "GET" }
+        };
+
+        var result = source.ToCocoaBreadcrumbData();
+
+        result.Should().NotBeNull();
+        result!.Count.Should().Be(2);
+        result[(NSString)"url"].Should().Be(NSObject.FromObject("https://example.com"));
+        result[(NSString)"method"].Should().Be(NSObject.FromObject("GET"));
+    }
+
+    [Fact]
+    public void ToCocoaBreadcrumbData_RequestStartKey_ConvertsToNSDate()
+    {
+        var timestamp = DateTimeOffset.UtcNow;
+        var unixMs = timestamp.ToUnixTimeMilliseconds();
+        var source = new Dictionary<string, string>
+        {
+            { SentryHttpMessageHandler.RequestStartKey, unixMs.ToString("F0", CultureInfo.InvariantCulture) }
+        };
+
+        var result = source.ToCocoaBreadcrumbData();
+
+        result.Should().NotBeNull();
+        result!.Count.Should().Be(1);
+        result[(NSString)SentryHttpMessageHandler.RequestStartKey].Should().BeOfType<NSDate>();
+    }
+
+    [Fact]
+    public void ToCocoaBreadcrumbData_RequestStartKey_NonNumericValue_FallsBackToNSObject()
+    {
+        var source = new Dictionary<string, string>
+        {
+            { SentryHttpMessageHandler.RequestStartKey, "not-a-number" }
+        };
+
+        var result = source.ToCocoaBreadcrumbData();
+
+        result.Should().NotBeNull();
+        result!.Count.Should().Be(1);
+        result[(NSString)SentryHttpMessageHandler.RequestStartKey].Should().Be(NSObject.FromObject("not-a-number"));
+    }
+
     private static void AssertEqual(SentryEvent managed, CocoaSdk.SentryEvent native)
     {
         native.ServerName.Should().Be(managed.ServerName, "Server Name");
diff --git a/test/Sentry.Tests/SentryHttpMessageHandlerTests.cs b/test/Sentry.Tests/SentryHttpMessageHandlerTests.cs
index f21d2a2237..14009a6549 100644
--- a/test/Sentry.Tests/SentryHttpMessageHandlerTests.cs
+++ b/test/Sentry.Tests/SentryHttpMessageHandlerTests.cs
@@ -611,30 +611,9 @@ public void Send_Executed_BreadcrumbCreated()
         Assert.True(breadcrumbGenerated.Data.ContainsKey(statusKey));
         Assert.Equal(expectedBreadcrumbData[statusKey], breadcrumbGenerated.Data[statusKey]);
     }
-
-    [Fact]
-    public void Send_Executed_FailedRequestsCaptured()
-    {
-        // Arrange
-        var hub = Substitute.For<IHub>();
-        var failedRequestHandler = Substitute.For<ISentryFailedRequestHandler>();
-        var options = new SentryOptions();
-        var url = "https://localhost/";
-
-        using var innerHandler = new FakeHttpMessageHandler();
-        using var sentryHandler = new SentryHttpMessageHandler(hub, options, innerHandler, failedRequestHandler);
-        using var client = new HttpClient(sentryHandler);
-
-        // Act
-        client.Get(url);
-
-        // Assert
-        failedRequestHandler.Received(1).HandleResponse(Arg.Any<HttpResponseMessage>());
-    }
-
 #endif
 
-#if ANDROID
+#if ANDROID || IOS || MACCATALYST
     [Fact]
     public void HandleResponse_SpanExists_AddsReplayBreadcrumbData()
     {
@@ -666,6 +645,7 @@ public void HandleResponse_SpanExists_AddsReplayBreadcrumbData()
         breadcrumb.Category.Should().Be("http");
 
         breadcrumb.Data.Should().NotBeNull();
+#if ANDROID
         breadcrumb.Data!.Should().ContainKey(SentryHttpMessageHandler.HttpStartTimestampKey);
         breadcrumb.Data.Should().ContainKey(SentryHttpMessageHandler.HttpEndTimestampKey);
 
@@ -673,11 +653,17 @@ public void HandleResponse_SpanExists_AddsReplayBreadcrumbData()
             .Should().BeTrue();
         long.TryParse(breadcrumb.Data![SentryHttpMessageHandler.HttpEndTimestampKey], NumberStyles.Integer, CultureInfo.InvariantCulture, out var endMs)
             .Should().BeTrue();
-
         startMs.Should().BeGreaterThan(0);
         startMs.Should().Be(span.StartTimestamp.ToUnixTimeMilliseconds());
         endMs.Should().BeGreaterThan(0);
         endMs.Should().BeGreaterOrEqualTo(startMs);
+#elif IOS || MACCATALYST
+        breadcrumb.Data!.Should().ContainKey(SentryHttpMessageHandler.RequestStartKey);
+        long.TryParse(breadcrumb.Data![SentryHttpMessageHandler.RequestStartKey], NumberStyles.Integer, CultureInfo.InvariantCulture, out var startMs)
+            .Should().BeTrue();
+        startMs.Should().BeGreaterThan(0);
+        startMs.Should().Be(span.StartTimestamp.ToUnixTimeMilliseconds());
+#endif
     }
 
     [Fact]
@@ -702,6 +688,7 @@ public void HandleResponse_NoSpanExists_NoReplayBreadcrumbData()
         breadcrumb.Data.Should().NotBeNull();
         breadcrumb.Data!.Should().NotContainKey(SentryHttpMessageHandler.HttpStartTimestampKey);
         breadcrumb.Data.Should().NotContainKey(SentryHttpMessageHandler.HttpEndTimestampKey);
+        breadcrumb.Data.Should().NotContainKey(SentryHttpMessageHandler.RequestStartKey);
     }
 #endif
 }