diff --git a/yt_dlp/utils.py b/yt_dlp/utils.py
index 84a8ecd6e..1532d22ac 100644
--- a/yt_dlp/utils.py
+++ b/yt_dlp/utils.py
@@ -986,16 +986,23 @@ def make_HTTPS_handler(params, **kwargs):
         context.options |= 4  # SSL_OP_LEGACY_SERVER_CONNECT
         # Allow use of weaker ciphers in Python 3.10+. See https://bugs.python.org/issue43998
         context.set_ciphers('DEFAULT')
-    elif sys.version_info < (3, 10) and ssl.OPENSSL_VERSION_INFO >= (1, 1, 1):
+    elif (
+        sys.version_info < (3, 10)
+        and ssl.OPENSSL_VERSION_INFO >= (1, 1, 1)
+        and not ssl.OPENSSL_VERSION.startswith('LibreSSL')
+    ):
         # Backport the default SSL ciphers and minimum TLS version settings from Python 3.10 [1].
         # This is to ensure consistent behavior across Python versions, and help avoid fingerprinting
         # in some situations [2][3].
         # Python 3.10 only supports OpenSSL 1.1.1+ [4]. Because this change is likely
         # untested on older versions, we only apply this to OpenSSL 1.1.1+ to be safe.
+        # LibreSSL is excluded until further investigation due to cipher support issues [5][6].
         # 1. https://github.com/python/cpython/commit/e983252b516edb15d4338b0a47631b59ef1e2536
         # 2. https://github.com/yt-dlp/yt-dlp/issues/4627
         # 3. https://github.com/yt-dlp/yt-dlp/pull/5294
         # 4. https://peps.python.org/pep-0644/
+        # 5. https://peps.python.org/pep-0644/#libressl-support
+        # 6. https://github.com/yt-dlp/yt-dlp/commit/5b9f253fa0aee996cf1ed30185d4b502e00609c4#commitcomment-89054368
         context.set_ciphers('@SECLEVEL=2:ECDH+AESGCM:ECDH+CHACHA20:ECDH+AES:DHE+AES:!aNULL:!eNULL:!aDSS:!SHA1:!AESCCM')
         context.minimum_version = ssl.TLSVersion.TLSv1_2