diff --git a/docs/testing/mypy.md b/docs/testing/mypy.md
index f6db236929..583661861c 100644
--- a/docs/testing/mypy.md
+++ b/docs/testing/mypy.md
@@ -148,6 +148,42 @@ because a list can have many elements, which would make the output too large.
 Similarly in dicts, one key's type and the corresponding value's type are printed.
 So `{1: 'a', 2: 'b', 3: 'c'}` will be printed as `{int: str, ...}`.
 
+## Using @overload to accurately describe variations
+
+Sometimes, a function's type is most precisely expressed as a few
+possibilites, and which possibility can be determined by looking at
+the arguments.  You can express that idea in a way mypy understands
+using `@overload`.  For example, `check_list` returns a `Validator`
+function that verifies that an object is a list, raising an exception
+if it isn't.
+
+It supports being passed a `sub_validator`, which will verify that
+each element in the list has a given type as well.  One can express
+the idea "If `sub_validator` validates that something is a `ResultT`,
+`check_list(sub_validator)` validators that something is a
+`List[ResultT]` as follows:
+
+~~~ py
+@overload
+def check_list(sub_validator: None, length: Optional[int]=None) -> Validator[List[object]]:
+    ...
+@overload
+def check_list(sub_validator: Validator[ResultT],
+               length: Optional[int]=None) -> Validator[List[ResultT]]:
+    ...
+def check_list(sub_validator: Optional[Validator[ResultT]]=None,
+               length: Optional[int]=None) -> Validator[List[ResultT]]:
+~~~
+
+The first overload expresses the types for the case where no
+`sub_validator` is passed, in which case all we know is that it
+returns a `Validator[List[object]]`; whereas the second defines the
+type logic for the case where we are passed a `sub_validator`.
+
+See the [mypy overloading documentation][mypy-overloads] for more details.
+
+[mypy-overloads]: https://mypy.readthedocs.io/en/stable/more_types.html#function-overloading
+
 ## Troubleshooting advice
 
 All of our linters, including mypy, are designed to only check files
diff --git a/zerver/lib/request.py b/zerver/lib/request.py
index d8247ba5f1..7823460d6f 100644
--- a/zerver/lib/request.py
+++ b/zerver/lib/request.py
@@ -137,7 +137,10 @@ class _REQ(Generic[ResultT]):
 # functions using has_request_variables. In reality, REQ returns an
 # instance of class _REQ to enable the decorator to scan the parameter
 # list for _REQ objects and patch the parameters as the true types.
-
+#
+# See also this documentation to learn how @overload helps here.
+# https://zulip.readthedocs.io/en/latest/testing/mypy.html#using-overload-to-accurately-describe-variations
+#
 # Overload 1: converter
 @overload
 def REQ(
diff --git a/zerver/lib/validator.py b/zerver/lib/validator.py
index 924ebae4db..fa89a9ceb5 100644
--- a/zerver/lib/validator.py
+++ b/zerver/lib/validator.py
@@ -186,6 +186,7 @@ def check_none_or(sub_validator: Validator[ResultT]) -> Validator[ResultT]:
             return sub_validator(var_name, val)
     return f
 
+# https://zulip.readthedocs.io/en/latest/testing/mypy.html#using-overload-to-accurately-describe-variations
 @overload
 def check_list(sub_validator: None, length: Optional[int]=None) -> Validator[List[object]]:
     ...
@@ -220,6 +221,7 @@ def check_list(sub_validator: Optional[Validator[ResultT]]=None, length: Optiona
         return cast(List[ResultT], val)
     return f
 
+# https://zulip.readthedocs.io/en/latest/testing/mypy.html#using-overload-to-accurately-describe-variations
 @overload
 def check_dict(required_keys: Iterable[Tuple[str, Validator[object]]]=[],
                optional_keys: Iterable[Tuple[str, Validator[object]]]=[],