diff --git a/CHANGES.rst b/CHANGES.rst
index b0ee624..3d508a6 100644
--- a/CHANGES.rst
+++ b/CHANGES.rst
@@ -1,6 +1,10 @@
 1.7.0 (unreleased)
 ==================
 
+- Fixing crashing sphinx builds where multiple directives are used with the
+  first one expecting content. The order of the directives used does not
+  matter after this fix. [#316]
+
 - Versions of Python <3.10 and pytest<7 are no longer supported. [#313]
 
 1.6.0 (2025-11-20)
diff --git a/pytest_doctestplus/sphinx/doctestplus.py b/pytest_doctestplus/sphinx/doctestplus.py
index 00b80f7..03ba7fd 100644
--- a/pytest_doctestplus/sphinx/doctestplus.py
+++ b/pytest_doctestplus/sphinx/doctestplus.py
@@ -10,9 +10,8 @@
 tests.
 """
 import re
-from docutils.nodes import literal_block
 from docutils.parsers.rst import Directive
-
+from sphinx.util.docutils import SphinxDirective
 
 class NoRunDirective(Directive):
     def run(self):
@@ -20,17 +19,17 @@ def run(self):
         return []
 
 
-class DoctestSkipDirective(Directive):
+class DoctestSkipDirective(SphinxDirective):
     has_content = True
 
     def run(self):
         # Check if there is any valid argument, and skip it. Currently only
         # 'win32' is supported.
-        if re.match('win32', self.content[0]):
+        if len(self.content) > 0 and re.match("win32", self.content[0]):
             self.content = self.content[2:]
-        code = '\n'.join(self.content)
-        return [literal_block(code, code)]
 
+        nodes = self.parse_content_to_nodes()
+        return nodes
 
 class DoctestOmitDirective(NoRunDirective):
     has_content = True
diff --git a/tests/docs/skip_some.rst b/tests/docs/skip_some.rst
index deceff0..2dd68fa 100644
--- a/tests/docs/skip_some.rst
+++ b/tests/docs/skip_some.rst
@@ -102,3 +102,41 @@ Code in doctest should run only if version condition is satisfied:
 .. doctest-requires:: pytest>=1.0 pytest>=2.0
 
     >>> import pytest
+
+
+Combined Directives
+===================
+
+
+Marking code with two directives:
+
+.. deprecated:: 1.0
+.. doctest-requires:: numpy<=0.1
+
+    >>> 1 + 3
+    2
+
+
+The order should not matter:
+
+.. doctest-requires:: numpy<=0.1
+.. deprecated:: 1.0
+
+    >>> 1 + 3
+    2
+
+Try two doctestplus directives:
+
+.. doctest-requires:: sys
+.. doctest-skip::
+
+    >>> 1 + 3
+    2
+
+Switch the order and it should still not run:
+
+.. doctest-skip::
+.. doctest-requires:: sys
+
+    >>> 1 + 3
+    2