diff --git a/README.asciidoc b/README.asciidoc
index ede9854c..eea1e6ba 100644
--- a/README.asciidoc
+++ b/README.asciidoc
@@ -726,15 +726,16 @@ Options are typed, their type can be
 
  * `int`: an integer number
  * `bool`: a boolean value, `yes/true` or `no/false`
- * `yesnoask`: similar to a boolean, but the additional
-   value `ask` is supported.
  * `str`: a string, some freeform text
  * `coord`: a line,column pair (separated by comma)
  * `regex`: as a string but the `set` commands will complain
    if the entered text is not a valid regex.
  * `{int,str}-list`: a list, elements are separated by a colon (:)
   if an element needs to contain a colon, it can be escaped with a
-   backslash.
+  backslash.
+ * `enum(value1|value2|...)`: an enum, taking on of the given values
+ * `flags(value1|value2|...)`: a set of flags, taking a combination
+   of the given values joined by `|`.
 
 Options value can be changed using the `set` commands:
 
@@ -781,7 +782,8 @@ Some options are built in Kakoune, and can be used to control it's behaviour:
    candidates exist, enable completion with common prefix.
  * `incsearch` _bool_: execute search as it is typed
  * `aligntab` _bool_: use tabs for alignement command
- * `autoinfo` _bool_: display automatic information box for certain commands.
+ * `autoinfo` _flags(command|onkey|normal)_: display automatic information
+   box in the enabled contexts.
  * `autoshowcompl` _bool_: automatically display possible completions when
    editing a prompt.
  * `ignored_files` _regex_: filenames matching this regex wont be considered
@@ -804,7 +806,7 @@ Some options are built in Kakoune, and can be used to control it's behaviour:
      element of the list should follow the format:
      _<line>.<column>[+<length>]@<timestamp>_ to define where the completion
      apply in the buffer, and the other strings are the candidates.
- * `autoreload` _yesnoask_: auto reload the buffers when an external
+ * `autoreload` _enum(yes|no|ask)_: auto reload the buffers when an external
    modification is detected.
  * `modelinefmt` _string_: A format string used to generate the mode line, that
    string is first expanded as a command line would be (expanding `%...{...}`
diff --git a/src/commands.cc b/src/commands.cc
index 9594223c..16114bff 100644
--- a/src/commands.cc
+++ b/src/commands.cc
@@ -1221,7 +1221,7 @@ void context_wrap(const ParametersParser& parser, Context& context, Func func)
 {
     // Disable these options to avoid costly code paths (and potential screen
     // redraws) That are useful only in interactive contexts.
-    DisableOption<int> disable_autoinfo(context, "autoinfo");
+    DisableOption<AutoInfo> disable_autoinfo(context, "autoinfo");
     DisableOption<bool> disable_autoshowcompl(context, "autoshowcompl");
     DisableOption<bool> disable_incsearch(context, "incsearch");
 
diff --git a/src/input_handler.cc b/src/input_handler.cc
index 80178984..353ced8a 100644
--- a/src/input_handler.cc
+++ b/src/input_handler.cc
@@ -251,7 +251,8 @@ public:
                                        { return lhs.key < rhs; });
             if (it != keymap.end() and it->key == key)
             {
-                if (context().options()["autoinfo"].get<int>() >= 2 and context().has_ui())
+                auto autoinfo = context().options()["autoinfo"].get<AutoInfo>();
+                if (autoinfo & AutoInfo::Normal and context().has_ui())
                     context().ui().info_show(key_to_str(key), it->docstring, CharCoord{},
                                              get_face("Information"), InfoStyle::Prompt);
 
@@ -1413,13 +1414,15 @@ DisplayLine InputHandler::mode_line() const
     return current_mode().mode_line();
 }
 
-
-bool show_auto_info_ifn(StringView title, StringView info, const Context& context)
+bool show_auto_info_ifn(StringView title, StringView info, AutoInfo mask, const Context& context)
 {
-    if (context.options()["autoinfo"].get<int>() < 1 or not context.has_ui())
+    if ((context.options()["autoinfo"].get<AutoInfo>() & mask) or
+        not context.has_ui())
         return false;
+
     Face face = get_face("Information");
     context.ui().info_show(title, info, CharCoord{}, face, InfoStyle::Prompt);
     return true;
 }
+
 }
diff --git a/src/input_handler.hh b/src/input_handler.hh
index 025f8979..49767eb4 100644
--- a/src/input_handler.hh
+++ b/src/input_handler.hh
@@ -103,13 +103,13 @@ private:
     int    m_handle_key_level = 0;
 };
 
-bool show_auto_info_ifn(StringView title, StringView info, const Context& context);
+bool show_auto_info_ifn(StringView title, StringView info, AutoInfo mask, const Context& context);
 
 template<typename Cmd>
 void on_next_key_with_autoinfo(const Context& context, KeymapMode keymap_mode, Cmd cmd,
                                StringView title, StringView info)
 {
-    const bool hide = show_auto_info_ifn(title, info, context);
+    const bool hide = show_auto_info_ifn(title, info, AutoInfo::OnKey, context);
     context.input_handler().on_next_key(
         keymap_mode, [hide,cmd](Key key, Context& context) mutable {
             if (hide)
diff --git a/src/main.cc b/src/main.cc
index 42424325..182f0c5f 100644
--- a/src/main.cc
+++ b/src/main.cc
@@ -201,7 +201,7 @@ void register_options()
                        true);
     reg.declare_option("autoinfo",
                        "automatically display contextual help",
-                       1);
+                       AutoInfo::Command | AutoInfo::OnKey);
     reg.declare_option("autoshowcompl",
                        "automatically display possible completions for prompts",
                        true);
diff --git a/src/normal.cc b/src/normal.cc
index 9b9f5088..009a2224 100644
--- a/src/normal.cc
+++ b/src/normal.cc
@@ -349,7 +349,8 @@ void command(Context& context, NormalParams params)
             if (context.has_ui())
             {
                 context.ui().info_hide();
-                if (event == PromptEvent::Change and context.options()["autoinfo"].get<int>() > 0)
+                auto autoinfo = context.options()["autoinfo"].get<AutoInfo>();
+                if (event == PromptEvent::Change and autoinfo & AutoInfo::Command)
                 {
                     Face face = get_face("Information");
                     if (cmdline.length() == 1 and is_horizontal_blank(cmdline[0_byte]))
diff --git a/src/option_types.hh b/src/option_types.hh
index d2161be2..a504efd7 100644
--- a/src/option_types.hh
+++ b/src/option_types.hh
@@ -7,6 +7,7 @@
 #include "coord.hh"
 #include "array_view.hh"
 #include "id_map.hh"
+#include "flags.hh"
 
 #include <tuple>
 #include <vector>
@@ -222,6 +223,45 @@ inline void option_from_string(StringView str, YesNoAsk& opt)
         throw runtime_error(format("invalid value '{}', expected yes, no or ask", str));
 }
 
+enum class AutoInfo
+{
+    None = 0,
+    Command = 1 << 0,
+    OnKey   = 1 << 1,
+    Normal  = 1 << 2
+};
+
+template<>
+struct WithBitOps<AutoInfo> : std::true_type {};
+
+inline String option_to_string(AutoInfo opt)
+{
+    String res;
+    if (opt & AutoInfo::Command)
+        res = "command";
+    if (opt & AutoInfo::OnKey)
+        res += res.empty() ? "onkey" : "|onkey";
+    if (opt & AutoInfo::Normal)
+        res += res.empty() ? "normal" : "|normal";
+    return res;
+}
+
+inline void option_from_string(StringView str, AutoInfo& opt)
+{
+    opt = AutoInfo::None;
+    for (auto s : split(str, '|'))
+    {
+        if (s == "command")
+            opt |= AutoInfo::Command;
+        else if (s == "onkey")
+            opt |= AutoInfo::OnKey;
+        else if (s == "normal")
+            opt |= AutoInfo::Normal;
+        else
+            throw runtime_error(format("invalid value '{}'", s));
+    }
+}
+
 }
 
 #endif // option_types_hh_INCLUDED