diff --git a/include/pybind11/pybind11.h b/include/pybind11/pybind11.h
index 74c8c0ff..44c4b61c 100644
--- a/include/pybind11/pybind11.h
+++ b/include/pybind11/pybind11.h
@@ -326,8 +326,10 @@ protected:
             signatures += "Overloaded function.\n\n";
         }
         // Then specific overload signatures
+        bool first_user_def = true;
         for (auto it = chain_start; it != nullptr; it = it->next) {
             if (options::show_function_signatures()) {
+                if (index > 0) signatures += "\n";
                 if (chain)
                     signatures += std::to_string(++index) + ". ";
                 signatures += rec->name;
@@ -335,12 +337,16 @@ protected:
                 signatures += "\n";
             }
             if (it->doc && strlen(it->doc) > 0 && options::show_user_defined_docstrings()) {
+                // If we're appending another docstring, and aren't printing function signatures, we
+                // need to append a newline first:
+                if (!options::show_function_signatures()) {
+                    if (first_user_def) first_user_def = false;
+                    else signatures += "\n";
+                }
                 if (options::show_function_signatures()) signatures += "\n";
                 signatures += it->doc;
                 if (options::show_function_signatures()) signatures += "\n";
             }
-            if (it->next)
-                signatures += "\n";
         }
 
         /* Install docstring */
diff --git a/tests/test_docstring_options.cpp b/tests/test_docstring_options.cpp
index 74178c27..9a9297cc 100644
--- a/tests/test_docstring_options.cpp
+++ b/tests/test_docstring_options.cpp
@@ -24,6 +24,15 @@ test_initializer docstring_generation([](py::module &m) {
         m.def("test_function1", [](int, int) {}, py::arg("a"), py::arg("b"));
         m.def("test_function2", [](int, int) {}, py::arg("a"), py::arg("b"), "A custom docstring");
 
+        m.def("test_overloaded1", [](int) {}, py::arg("i"), "Overload docstring");
+        m.def("test_overloaded1", [](double) {}, py::arg("d"));
+
+        m.def("test_overloaded2", [](int) {}, py::arg("i"), "overload docstring 1");
+        m.def("test_overloaded2", [](double) {}, py::arg("d"), "overload docstring 2");
+
+        m.def("test_overloaded3", [](int) {}, py::arg("i"));
+        m.def("test_overloaded3", [](double) {}, py::arg("d"), "Overload docstr");
+
         options.enable_function_signatures();
 
         m.def("test_function3", [](int, int) {}, py::arg("a"), py::arg("b"));
diff --git a/tests/test_docstring_options.py b/tests/test_docstring_options.py
index 66ad6b89..5e40f686 100644
--- a/tests/test_docstring_options.py
+++ b/tests/test_docstring_options.py
@@ -3,13 +3,23 @@
 def test_docstring_options():
     from pybind11_tests import (test_function1, test_function2, test_function3,
                                 test_function4, test_function5, test_function6,
-                                test_function7, DocstringTestFoo)
+                                test_function7, DocstringTestFoo,
+                                test_overloaded1, test_overloaded2, test_overloaded3)
 
     # options.disable_function_signatures()
     assert not test_function1.__doc__
 
     assert test_function2.__doc__ == "A custom docstring"
 
+    # docstring specified on just the first overload definition:
+    assert test_overloaded1.__doc__ == "Overload docstring"
+
+    # docstring on both overloads:
+    assert test_overloaded2.__doc__ == "overload docstring 1\noverload docstring 2"
+
+    # docstring on only second overload:
+    assert test_overloaded3.__doc__ == "Overload docstr"
+
     # options.enable_function_signatures()
     assert test_function3.__doc__ .startswith("test_function3(a: int, b: int) -> None")