diff --git a/CHANGELOG.md b/CHANGELOG.md
index 98eacde70..5deb5da30 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -4,6 +4,7 @@
 
 **Features**:
 
+- Windows: report WINE and Proton metadata in a separate runtime context. ([#1995](https://github.com/getsentry/sentry-native/pull/1995))
 - Add a public custom HTTP transport client interface (`sentry_http_transport_new`) so applications can plug in their own HTTP client (e.g. platform-native ones) while sentry-native continues to own request queueing, retry/backoff, offline caching, rate-limiting, and client reports. The built-in curl and WinHTTP transports are now implemented against this same interface. ([#1987](https://github.com/getsentry/sentry-native/pull/1987))
 - Native/Windows: capture WER report ID and expose as `contexts.wer.report_id` in crash events when the WER integration is enabled. ([#1970](https://github.com/getsentry/sentry-native/pull/1970))
 - Add `sentry_set_tags` and `sentry_scope_set_tags` for updating multiple tags with a single scope flush, improving bulk-update performance. ([#1993](https://github.com/getsentry/sentry-native/pull/1993))
diff --git a/src/sentry_os.c b/src/sentry_os.c
index e1bb18cb9..b67a3d0cc 100644
--- a/src/sentry_os.c
+++ b/src/sentry_os.c
@@ -1,4 +1,5 @@
 #include "sentry_os.h"
+#include "sentry_path.h"
 #include "sentry_slice.h"
 #include "sentry_string.h"
 #if defined(SENTRY_PLATFORM_LINUX) || defined(SENTRY_PLATFORM_WINDOWS)
@@ -178,6 +179,204 @@ sentry__get_windows_version(windows_version_t *win_ver)
     return 1;
 }
 
+static bool
+string_ends_with(const char *value, size_t value_len, const char *suffix)
+{
+    const size_t suffix_len = strlen(suffix);
+    return value_len >= suffix_len
+        && memcmp(value + value_len - suffix_len, suffix, suffix_len) == 0;
+}
+
+static char *
+make_wine_path(const char *path, const char *suffix)
+{
+    sentry_stringbuilder_t sb;
+    sentry__stringbuilder_init(&sb);
+    if (sentry__stringbuilder_append(&sb, "Z:")
+        || sentry__stringbuilder_append(&sb, path)
+        || sentry__stringbuilder_append(&sb, suffix)) {
+        sentry__stringbuilder_cleanup(&sb);
+        return NULL;
+    }
+    return sentry__stringbuilder_into_string(&sb);
+}
+
+static char *
+read_wine_file(const char *path)
+{
+    sentry_path_t *file_path = sentry__path_from_str(path);
+    char *contents
+        = file_path ? sentry__path_read_to_buffer(file_path, NULL) : NULL;
+    sentry__path_free(file_path);
+    return contents;
+}
+
+static char *
+get_proton_version(bool *is_proton)
+{
+    *is_proton = false;
+    char *compat_path
+        = sentry__string_from_wstr(_wgetenv(L"STEAM_COMPAT_DATA_PATH"));
+    if (!compat_path || !compat_path[0]) {
+        sentry_free(compat_path);
+        return NULL;
+    }
+
+    char *config_path = make_wine_path(compat_path, "/config_info");
+    sentry_free(compat_path);
+    char *config = config_path ? read_wine_file(config_path) : NULL;
+    sentry_free(config_path);
+    if (!config) {
+        return NULL;
+    }
+
+    char *fonts_path = strchr(config, '\n');
+    if (!fonts_path) {
+        sentry_free(config);
+        return NULL;
+    }
+    fonts_path++;
+    while (*fonts_path == ' ' || *fonts_path == '\t') {
+        fonts_path++;
+    }
+    size_t fonts_path_len = strcspn(fonts_path, "\r\n");
+    while (fonts_path_len > 0
+        && (fonts_path[fonts_path_len - 1] == ' '
+            || fonts_path[fonts_path_len - 1] == '\t')) {
+        fonts_path_len--;
+    }
+
+    const char *fonts_suffix = NULL;
+    if (string_ends_with(fonts_path, fonts_path_len, "/files/share/fonts/")) {
+        fonts_suffix = "/files/share/fonts/";
+    } else if (string_ends_with(
+                   fonts_path, fonts_path_len, "/dist/share/fonts/")) {
+        fonts_suffix = "/dist/share/fonts/";
+    }
+    if (!fonts_suffix) {
+        sentry_free(config);
+        return NULL;
+    }
+
+    const size_t root_len = fonts_path_len - strlen(fonts_suffix);
+    char *proton_root = sentry__string_clone_n(fonts_path, root_len);
+    sentry_free(config);
+    if (!proton_root) {
+        return NULL;
+    }
+
+    char *proton_path = make_wine_path(proton_root, "/proton");
+    sentry_path_t *proton_file = sentry__path_from_str(proton_path);
+    *is_proton = proton_file && sentry__path_is_file(proton_file);
+    sentry__path_free(proton_file);
+    sentry_free(proton_path);
+
+    char *version_path = make_wine_path(proton_root, "/version");
+    sentry_free(proton_root);
+    char *version_file = version_path ? read_wine_file(version_path) : NULL;
+    sentry_free(version_path);
+    if (!version_file) {
+        return NULL;
+    }
+
+    char *version = strpbrk(version_file, " \t");
+    if (!version) {
+        sentry_free(version_file);
+        return NULL;
+    }
+    while (*version == ' ' || *version == '\t') {
+        version++;
+    }
+    size_t version_len = strcspn(version, "\r\n");
+    while (version_len > 0
+        && (version[version_len - 1] == ' '
+            || version[version_len - 1] == '\t')) {
+        version_len--;
+    }
+
+    char *result
+        = version_len ? sentry__string_clone_n(version, version_len) : NULL;
+    sentry_free(version_file);
+    return result;
+}
+
+static bool
+string_starts_with(const char *value, const char *prefix)
+{
+    const size_t value_len = strlen(value);
+    const size_t prefix_len = strlen(prefix);
+    return value_len >= prefix_len && memcmp(value, prefix, prefix_len) == 0;
+}
+
+sentry_value_t
+sentry__make_wine_context(sentry__wine_get_version_t wine_get_version,
+    const char *proton_version, bool is_proton)
+{
+    if (!wine_get_version) {
+        return sentry_value_new_null();
+    }
+
+    const char *runtime_name = "Wine";
+    const char *runtime_version = wine_get_version();
+    if (!runtime_version || !runtime_version[0]) {
+        return sentry_value_new_null();
+    }
+
+    if (proton_version && proton_version[0]) {
+        runtime_version = proton_version;
+        if (is_proton) {
+            if (string_starts_with(proton_version, "proton-")) {
+                runtime_name = "Proton";
+                runtime_version += strlen("proton-");
+            } else if (string_starts_with(proton_version, "experimental-")) {
+                runtime_name = "Proton Experimental";
+                runtime_version += strlen("experimental-");
+            } else if (string_starts_with(proton_version, "GE-Proton")) {
+                runtime_name = "GE-Proton";
+                runtime_version += strlen("GE-Proton");
+            } else if (string_starts_with(proton_version, "hotfix-")) {
+                runtime_name = "Proton Hotfix";
+                runtime_version += strlen("hotfix-");
+            } else {
+                runtime_name = "Proton Custom";
+            }
+        }
+    }
+
+    sentry_value_t context = sentry_value_new_object();
+    if (sentry_value_is_null(context)) {
+        return context;
+    }
+    sentry_value_set_by_key(
+        context, "type", sentry_value_new_string("runtime"));
+    sentry_value_set_by_key(
+        context, "name", sentry_value_new_string(runtime_name));
+    if (runtime_version[0]) {
+        sentry_value_set_by_key(
+            context, "version", sentry_value_new_string(runtime_version));
+    }
+    sentry_value_freeze(context);
+    return context;
+}
+
+sentry_value_t
+sentry__get_wine_context(void)
+{
+    const HMODULE ntdll = GetModuleHandleW(L"ntdll.dll");
+    if (!ntdll) {
+        return sentry_value_new_null();
+    }
+
+    const sentry__wine_get_version_t wine_get_version
+        = (sentry__wine_get_version_t)GetProcAddress(ntdll, "wine_get_version");
+    bool is_proton = false;
+    char *proton_version = get_proton_version(&is_proton);
+    sentry_value_t context = sentry__make_wine_context(
+        wine_get_version, proton_version, is_proton);
+    sentry_free(proton_version);
+    return context;
+}
+
 #    endif // !defined(SENTRY_PLATFORM_XBOX)
 
 sentry_value_t
diff --git a/src/sentry_os.h b/src/sentry_os.h
index 41d1b6b14..ed701dfb9 100644
--- a/src/sentry_os.h
+++ b/src/sentry_os.h
@@ -52,6 +52,16 @@ typedef struct {
 
 int sentry__get_kernel_version(windows_version_t *win_ver);
 int sentry__get_windows_version(windows_version_t *win_ver);
+
+#    if !defined(SENTRY_PLATFORM_XBOX)
+typedef const char *(CDECL *sentry__wine_get_version_t)(void);
+
+sentry_value_t sentry__make_wine_context(
+    sentry__wine_get_version_t wine_get_version, const char *proton_version,
+    bool is_proton);
+sentry_value_t sentry__get_wine_context(void);
+#    endif
+
 void sentry__set_default_thread_stack_guarantee(void);
 void sentry__init_cached_kernel32_functions(void);
 void sentry__get_system_time(LPFILETIME filetime);
diff --git a/src/sentry_scope.c b/src/sentry_scope.c
index 0bb7057e1..35a0cc654 100644
--- a/src/sentry_scope.c
+++ b/src/sentry_scope.c
@@ -109,6 +109,14 @@ get_scope(void)
     init_scope(&g_scope);
     g_scope.user = sentry_value_new_object();
     sentry_value_set_by_key(g_scope.contexts, "os", sentry__get_os_context());
+#if defined(SENTRY_PLATFORM_WINDOWS) && !defined(SENTRY_PLATFORM_XBOX)
+    sentry_value_t wine_context = sentry__get_wine_context();
+    if (!sentry_value_is_null(wine_context)) {
+        sentry_value_set_by_key(g_scope.contexts, "wine", wine_context);
+    } else {
+        sentry_value_decref(wine_context);
+    }
+#endif
     g_scope.client_sdk = get_client_sdk();
 
     g_scope_initialized = true;
diff --git a/tests/unit/test_os.c b/tests/unit/test_os.c
index 5a4d3337c..4f260a418 100644
--- a/tests/unit/test_os.c
+++ b/tests/unit/test_os.c
@@ -200,6 +200,21 @@ extern void(WINAPI *g_kernel32_GetCurrentThreadStackLimits)(
     PULONG_PTR, PULONG_PTR);
 static size_t g_kernel32_SetThreadStackGuaranteeCalled = 0;
 
+#    if !defined(SENTRY_PLATFORM_XBOX)
+static const char *CDECL
+wine_get_version(void)
+{
+    return "9.0";
+}
+
+static const char *CDECL
+wine_get_empty_version(void)
+{
+    return "";
+}
+
+#    endif
+
 static BOOL WINAPI
 no_previous_guarantee(PULONG guarantee)
 {
@@ -295,6 +310,105 @@ stack_reserve_exact_factor_minus_one(PULONG_PTR low, PULONG_PTR high)
 }
 #endif
 
+SENTRY_TEST(wine_context)
+{
+#if !defined(SENTRY_PLATFORM_WINDOWS) || defined(SENTRY_PLATFORM_XBOX)
+    SKIP_TEST();
+#else
+    sentry_value_t context
+        = sentry__make_wine_context(wine_get_version, NULL, false);
+    TEST_CHECK(!sentry_value_is_null(context));
+    TEST_CHECK(sentry_value_is_frozen(context));
+    TEST_CHECK_STRING_EQUAL(
+        sentry_value_as_string(sentry_value_get_by_key(context, "type")),
+        "runtime");
+    TEST_CHECK_STRING_EQUAL(
+        sentry_value_as_string(sentry_value_get_by_key(context, "name")),
+        "Wine");
+    TEST_CHECK_STRING_EQUAL(
+        sentry_value_as_string(sentry_value_get_by_key(context, "version")),
+        "9.0");
+    sentry_value_decref(context);
+
+    context
+        = sentry__make_wine_context(wine_get_version, "proton-10.0-4", true);
+    TEST_CHECK_STRING_EQUAL(
+        sentry_value_as_string(sentry_value_get_by_key(context, "name")),
+        "Proton");
+    TEST_CHECK_STRING_EQUAL(
+        sentry_value_as_string(sentry_value_get_by_key(context, "version")),
+        "10.0-4");
+    sentry_value_decref(context);
+
+    context = sentry__make_wine_context(
+        wine_get_version, "experimental-10.0-20260113", true);
+    TEST_CHECK_STRING_EQUAL(
+        sentry_value_as_string(sentry_value_get_by_key(context, "name")),
+        "Proton Experimental");
+    TEST_CHECK_STRING_EQUAL(
+        sentry_value_as_string(sentry_value_get_by_key(context, "version")),
+        "10.0-20260113");
+    sentry_value_decref(context);
+
+    context
+        = sentry__make_wine_context(wine_get_version, "GE-Proton9-27", true);
+    TEST_CHECK_STRING_EQUAL(
+        sentry_value_as_string(sentry_value_get_by_key(context, "name")),
+        "GE-Proton");
+    TEST_CHECK_STRING_EQUAL(
+        sentry_value_as_string(sentry_value_get_by_key(context, "version")),
+        "9-27");
+    sentry_value_decref(context);
+
+    context
+        = sentry__make_wine_context(wine_get_version, "GE-Proton", true);
+    TEST_CHECK_STRING_EQUAL(
+        sentry_value_as_string(sentry_value_get_by_key(context, "name")),
+        "GE-Proton");
+    TEST_CHECK(sentry_value_is_null(
+        sentry_value_get_by_key(context, "version")));
+    sentry_value_decref(context);
+
+    context
+        = sentry__make_wine_context(wine_get_version, "hotfix-20251031", true);
+    TEST_CHECK_STRING_EQUAL(
+        sentry_value_as_string(sentry_value_get_by_key(context, "name")),
+        "Proton Hotfix");
+    TEST_CHECK_STRING_EQUAL(
+        sentry_value_as_string(sentry_value_get_by_key(context, "version")),
+        "20251031");
+    sentry_value_decref(context);
+
+    context
+        = sentry__make_wine_context(wine_get_version, "custom-tool-1", true);
+    TEST_CHECK_STRING_EQUAL(
+        sentry_value_as_string(sentry_value_get_by_key(context, "name")),
+        "Proton Custom");
+    TEST_CHECK_STRING_EQUAL(
+        sentry_value_as_string(sentry_value_get_by_key(context, "version")),
+        "custom-tool-1");
+    sentry_value_decref(context);
+
+    context
+        = sentry__make_wine_context(wine_get_version, "wine-ge-8-26", false);
+    TEST_CHECK_STRING_EQUAL(
+        sentry_value_as_string(sentry_value_get_by_key(context, "name")),
+        "Wine");
+    TEST_CHECK_STRING_EQUAL(
+        sentry_value_as_string(sentry_value_get_by_key(context, "version")),
+        "wine-ge-8-26");
+    sentry_value_decref(context);
+
+    context = sentry__make_wine_context(NULL, NULL, false);
+    TEST_CHECK(sentry_value_is_null(context));
+    sentry_value_decref(context);
+
+    context = sentry__make_wine_context(wine_get_empty_version, NULL, false);
+    TEST_CHECK(sentry_value_is_null(context));
+    sentry_value_decref(context);
+#endif
+}
+
 SENTRY_TEST(stack_guarantee)
 {
 #if !defined(SENTRY_PLATFORM_WINDOWS)
diff --git a/tests/unit/tests.inc b/tests/unit/tests.inc
index f3af596d0..dd27dc136 100644
--- a/tests/unit/tests.inc
+++ b/tests/unit/tests.inc
@@ -524,6 +524,7 @@ XX(value_uint64)
 XX(value_unicode)
 XX(value_user)
 XX(value_wrong_type)
+XX(wine_context)
 XX(write_envelope_partial_write_fails)
 XX(write_raw_envelope_to_file)
 XX(writer_byte_count_stops_after_failure)