diff --git a/Misc/NEWS.d/next/Windows/2023-07-24-13-35-22.gh-issue-107078.leZSPg.rst b/Misc/NEWS.d/next/Windows/2023-07-24-13-35-22.gh-issue-107078.leZSPg.rst
new file mode 100644
index 00000000000000..82089f61a01aa2
--- /dev/null
+++ b/Misc/NEWS.d/next/Windows/2023-07-24-13-35-22.gh-issue-107078.leZSPg.rst
@@ -0,0 +1 @@
+Fix `_datetimemodule.c` when calling `datetime.datetime.fromtimestamp(0).astimezone()` with `OSError` on Windows
diff --git a/Modules/_datetimemodule.c b/Modules/_datetimemodule.c
index b8cb0c012fd537..18842b379ca1a7 100644
--- a/Modules/_datetimemodule.c
+++ b/Modules/_datetimemodule.c
@@ -6333,9 +6333,18 @@ local_to_seconds(int year, int month, int day,
             u2 = u1 + max_fold_seconds;
         else
             u2 = u1 - max_fold_seconds;
+#ifdef MS_WINDOWS
+        u2 += max_fold_seconds;
+#endif
+
         lt = local(u2);
         if (lt == -1)
             return -1;
+#ifdef MS_WINDOWS
+        u2 -= max_fold_seconds;
+        lt -= max_fold_seconds;
+#endif
+
         b = lt - u2;
         if (a == b)
             return u1;