diff --git a/CHANGELOG.md b/CHANGELOG.md
index 63c642e22..1eda15f72 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -18,6 +18,7 @@
 
 - Update Xbox toolchain to include `UseDebugLibraries` fix for Debug builds. ([#1302](https://github.com/getsentry/sentry-native/pull/1302))
 - Fix GDK version selection for Xbox by propagating `XdkEditionTarget` to MSBuild. ([#1312](https://github.com/getsentry/sentry-native/pull/1312))
+- Fix WinHTTP initialization timing to prevent error 12007 on Xbox platform. ([#1321](https://github.com/getsentry/sentry-native/pull/1321))
 
 **Meta**:
 
diff --git a/CMakeLists.txt b/CMakeLists.txt
index 98f30edff..fd6d56afd 100644
--- a/CMakeLists.txt
+++ b/CMakeLists.txt
@@ -489,7 +489,7 @@ elseif(LINUX)
 	set(_SENTRY_PLATFORM_LIBS "dl" "rt")
 elseif(WIN32)
 	if (XBOX)
-		set(_SENTRY_PLATFORM_LIBS "version")
+		set(_SENTRY_PLATFORM_LIBS "version" "xgameruntime")
 	else()
 		set(_SENTRY_PLATFORM_LIBS "dbghelp" "shlwapi" "version")
 	endif()
diff --git a/src/CMakeLists.txt b/src/CMakeLists.txt
index a34a54004..46742197c 100644
--- a/src/CMakeLists.txt
+++ b/src/CMakeLists.txt
@@ -112,6 +112,11 @@ elseif(SENTRY_TRANSPORT_WINHTTP)
 	sentry_target_sources_cwd(sentry
 		transports/sentry_transport_winhttp.c
 	)
+	if (XBOX)
+		sentry_target_sources_cwd(sentry
+			transports/sentry_transport_xnetworking.cpp
+		)
+	endif()
 elseif(SENTRY_TRANSPORT_NONE)
 	sentry_target_sources_cwd(sentry
 		transports/sentry_transport_none.c
diff --git a/src/transports/sentry_transport_winhttp.c b/src/transports/sentry_transport_winhttp.c
index d9c7b60b1..659c182b8 100644
--- a/src/transports/sentry_transport_winhttp.c
+++ b/src/transports/sentry_transport_winhttp.c
@@ -13,6 +13,10 @@
 #include <string.h>
 #include <winhttp.h>
 
+#ifdef SENTRY_PLATFORM_XBOX
+HRESULT sentry__transport_ensure_network_initialized();
+#endif // SENTRY_PLATFORM_XBOX
+
 typedef struct {
     sentry_dsn_t *dsn;
     wchar_t *user_agent;
@@ -40,6 +44,31 @@ sentry__winhttp_bgworker_state_new(void)
     return state;
 }
 
+static void
+sentry__winhttp_session_start(void *_state)
+{
+    winhttp_bgworker_state_t *state = _state;
+    if (state->proxy) {
+        state->session
+            = WinHttpOpen(state->user_agent, WINHTTP_ACCESS_TYPE_NAMED_PROXY,
+                state->proxy, WINHTTP_NO_PROXY_BYPASS, 0);
+    } else {
+#if _WIN32_WINNT >= 0x0603
+        state->session = WinHttpOpen(state->user_agent,
+            WINHTTP_ACCESS_TYPE_AUTOMATIC_PROXY, WINHTTP_NO_PROXY_NAME,
+            WINHTTP_NO_PROXY_BYPASS, 0);
+#endif
+        // On windows 8.0 or lower, WINHTTP_ACCESS_TYPE_AUTOMATIC_PROXY does
+        // not work on error we fallback to
+        // WINHTTP_ACCESS_TYPE_DEFAULT_PROXY
+        if (!state->session) {
+            state->session = WinHttpOpen(state->user_agent,
+                WINHTTP_ACCESS_TYPE_DEFAULT_PROXY, WINHTTP_NO_PROXY_NAME,
+                WINHTTP_NO_PROXY_BYPASS, 0);
+        }
+    }
+}
+
 static void
 sentry__winhttp_bgworker_state_free(void *_state)
 {
@@ -118,28 +147,14 @@ sentry__winhttp_transport_start(
         }
     }
 
-    if (state->proxy) {
-        state->session
-            = WinHttpOpen(state->user_agent, WINHTTP_ACCESS_TYPE_NAMED_PROXY,
-                state->proxy, WINHTTP_NO_PROXY_BYPASS, 0);
-    } else {
-#if _WIN32_WINNT >= 0x0603
-        state->session = WinHttpOpen(state->user_agent,
-            WINHTTP_ACCESS_TYPE_AUTOMATIC_PROXY, WINHTTP_NO_PROXY_NAME,
-            WINHTTP_NO_PROXY_BYPASS, 0);
-#endif
-        // On windows 8.0 or lower, WINHTTP_ACCESS_TYPE_AUTOMATIC_PROXY does
-        // not work on error we fallback to WINHTTP_ACCESS_TYPE_DEFAULT_PROXY
-        if (!state->session) {
-            state->session = WinHttpOpen(state->user_agent,
-                WINHTTP_ACCESS_TYPE_DEFAULT_PROXY, WINHTTP_NO_PROXY_NAME,
-                WINHTTP_NO_PROXY_BYPASS, 0);
-        }
-    }
+#ifndef SENTRY_PLATFORM_XBOX
+    sentry__winhttp_session_start(state);
+
     if (!state->session) {
         SENTRY_WARN("`WinHttpOpen` failed");
         return 1;
     }
+#endif // !SENTRY_PLATFORM_XBOX
 
     return sentry__bgworker_start(bgworker);
 }
@@ -187,6 +202,20 @@ sentry__winhttp_send_task(void *_envelope, void *_state)
     sentry_envelope_t *envelope = (sentry_envelope_t *)_envelope;
     winhttp_bgworker_state_t *state = (winhttp_bgworker_state_t *)_state;
 
+#ifdef SENTRY_PLATFORM_XBOX
+    if (!state->session) {
+        SENTRY_DEBUG(
+            "ensuring xbox network is initialized for WinHttp transport");
+        sentry__transport_ensure_network_initialized();
+        sentry__winhttp_session_start(state);
+
+        if (!state->session) {
+            SENTRY_WARN("`WinHttpOpen` failed");
+            return;
+        }
+    }
+#endif // SENTRY_PLATFORM_XBOX
+
     uint64_t started = sentry__monotonic_time();
 
     char *user_agent = sentry__string_from_wstr(state->user_agent);
diff --git a/src/transports/sentry_transport_xnetworking.cpp b/src/transports/sentry_transport_xnetworking.cpp
new file mode 100644
index 000000000..4af10ecd8
--- /dev/null
+++ b/src/transports/sentry_transport_xnetworking.cpp
@@ -0,0 +1,64 @@
+#include "sentry_boot.h"
+
+#include <XNetworking.h>
+
+static void
+sentry__transport_network_connectivity_hint_changed_callback(_In_ void *context,
+    _In_ const XNetworkingConnectivityHint *connectivity_hint)
+{
+    HANDLE network_initialized_event = static_cast<HANDLE>(context);
+    if (connectivity_hint->networkInitialized) {
+        (void)SetEvent(network_initialized_event);
+    }
+}
+
+extern "C" {
+
+HRESULT
+sentry__transport_ensure_network_initialized()
+{
+    HRESULT hr = S_OK;
+    XNetworkingConnectivityHint connectivity_hint;
+    XTaskQueueHandle queue;
+
+    hr = XTaskQueueCreate(XTaskQueueDispatchMode::Immediate,
+        XTaskQueueDispatchMode::Immediate, &queue);
+    if (SUCCEEDED(hr)) {
+        // Use the new XNetworking APIs to check if the network is initialized.
+        hr = XNetworkingGetConnectivityHint(&connectivity_hint);
+        if (SUCCEEDED(hr)) {
+            if (!connectivity_hint.networkInitialized) {
+                // The network isn't initialized. Wait until the network becomes
+                // initialized.
+                HANDLE network_initialized_event
+                    = CreateEvent(nullptr, TRUE, FALSE, nullptr);
+                if (network_initialized_event != nullptr) {
+                    XTaskQueueRegistrationToken token;
+                    hr = XNetworkingRegisterConnectivityHintChanged(queue,
+                        network_initialized_event,
+                        sentry__transport_network_connectivity_hint_changed_callback,
+                        &token);
+                    if (SUCCEEDED(hr)) {
+                        DWORD result = WaitForSingleObjectEx(
+                            network_initialized_event, INFINITE, FALSE);
+                        if (result != WAIT_OBJECT_0) {
+                            hr = HRESULT_FROM_WIN32(GetLastError());
+                        }
+
+                        XNetworkingUnregisterConnectivityHintChanged(
+                            token, true);
+                    }
+
+                    CloseHandle(network_initialized_event);
+                } else {
+                    hr = HRESULT_FROM_WIN32(GetLastError());
+                }
+            }
+        }
+
+        XTaskQueueCloseHandle(queue);
+    }
+
+    return hr;
+}
+}