diff --git a/CHANGELOG.md b/CHANGELOG.md
index 4a87f54041..eb7d4cc404 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -7,6 +7,7 @@
 - Apply the propagation context to events that already have contexts set, so that events captured with a local scope or with event-level contexts keep their trace. ([#1843](https://github.com/getsentry/sentry-native/pull/1843))
 - Route libcurl debug output through the Sentry logger (`SENTRY_TRACE`) instead of writing to `stderr`. ([#1854](https://github.com/getsentry/sentry-native/pull/1854))
   - NOTE: `sentry_options_set_debug(options, true)` no longer displays verbose libcurl debug output by default. To restore it, call `sentry_options_set_logger_level(options, SENTRY_LEVEL_TRACE)`.
+- Windows: fix symlink detection used to prevent database cleanup from following symlinks in run and cache directories. ([#1857](https://github.com/getsentry/sentry-native/pull/1857))
 
 ## 0.15.3
 
diff --git a/src/path/sentry_path_windows.c b/src/path/sentry_path_windows.c
index b27b4d2486..7169a89afd 100644
--- a/src/path/sentry_path_windows.c
+++ b/src/path/sentry_path_windows.c
@@ -359,8 +359,21 @@ sentry__path_is_symlink(const sentry_path_t *path)
         return false;
     }
     const DWORD attributes = GetFileAttributesW(path_w);
-    return attributes != INVALID_FILE_ATTRIBUTES
-        && (attributes & FILE_ATTRIBUTE_REPARSE_POINT) != 0;
+    if (attributes == INVALID_FILE_ATTRIBUTES
+        || (attributes & FILE_ATTRIBUTE_REPARSE_POINT) == 0) {
+        return false;
+    }
+
+    // https://learn.microsoft.com/en-us/windows/win32/fileio/reparse-point-tags
+    WIN32_FIND_DATAW data;
+    const HANDLE find_handle = FindFirstFileW(path_w, &data);
+    if (find_handle == INVALID_HANDLE_VALUE) {
+        return true;
+    }
+    FindClose(find_handle);
+
+    return (data.dwFileAttributes & FILE_ATTRIBUTE_REPARSE_POINT) != 0
+        && IsReparseTagNameSurrogate(data.dwReserved0) != 0;
 }
 
 size_t
diff --git a/src/sentry_path.h b/src/sentry_path.h
index 4275c01754..afe8247905 100644
--- a/src/sentry_path.h
+++ b/src/sentry_path.h
@@ -149,7 +149,8 @@ bool sentry__path_ends_with(const sentry_path_t *path, const char *suffix);
 bool sentry__path_is_dir(const sentry_path_t *path);
 
 /**
- * Return whether the path refers to a symlink.
+ * Return whether the path refers to a symlink. On Windows, this includes
+ * name-surrogate reparse points such as junctions.
  */
 bool sentry__path_is_symlink(const sentry_path_t *path);
 
diff --git a/tests/unit/test_path.c b/tests/unit/test_path.c
index 6b782e8285..7ebe2045a9 100644
--- a/tests/unit/test_path.c
+++ b/tests/unit/test_path.c
@@ -2,7 +2,27 @@
 #include "sentry_string.h"
 #include "sentry_testsupport.h"
 
-#if defined(SENTRY_PLATFORM_UNIX) && !defined(SENTRY_PLATFORM_NX)              \
+#if defined(SENTRY_PLATFORM_WINDOWS) && !defined(SENTRY_PLATFORM_XBOX)
+static int
+symlink(const char *target, const char *link)
+{
+    sentry_path_t *target_path = sentry__path_from_str(target);
+    sentry_path_t *link_path = sentry__path_from_str(link);
+    if (!target_path || !link_path) {
+        sentry__path_free(link_path);
+        sentry__path_free(target_path);
+        return -1;
+    }
+
+    BOOLEAN success
+        = CreateSymbolicLinkW(link_path->path_w, target_path->path_w,
+            SYMBOLIC_LINK_FLAG_DIRECTORY
+                | SYMBOLIC_LINK_FLAG_ALLOW_UNPRIVILEGED_CREATE);
+    sentry__path_free(link_path);
+    sentry__path_free(target_path);
+    return success ? 0 : -1;
+}
+#elif defined(SENTRY_PLATFORM_UNIX) && !defined(SENTRY_PLATFORM_NX)            \
     && !defined(SENTRY_PLATFORM_PS)
 #    include <unistd.h>
 #endif
@@ -254,8 +274,8 @@ SENTRY_TEST(path_directory)
 
 SENTRY_TEST(path_remove_all_symlink)
 {
-#if !defined(SENTRY_PLATFORM_UNIX) || defined(SENTRY_PLATFORM_NX)              \
-    || defined(SENTRY_PLATFORM_PS)
+#if defined(SENTRY_PLATFORM_NX) || defined(SENTRY_PLATFORM_PS)                 \
+    || defined(SENTRY_PLATFORM_XBOX)
     SKIP_TEST();
 #else
     sentry_path_t *base