diff --git a/src/regex_impl.cc b/src/regex_impl.cc
index 09c8cc02..2e3b9ccf 100644
--- a/src/regex_impl.cc
+++ b/src/regex_impl.cc
@@ -474,8 +474,13 @@ private:
     void validate_lookaround(const AstNodePtr& node)
     {
         for (auto& child : node->children)
-            if (child->op != ParsedRegex::Literal)
-                parse_error("Lookaround can only contain literals");
+        {
+            if (child->op != ParsedRegex::Literal and child->op != ParsedRegex::Matcher and
+                child->op != ParsedRegex::AnyChar)
+                parse_error("Lookaround can only contain literals, any chars or character classes");
+            if (child->quantifier.type != ParsedRegex::Quantifier::One)
+                parse_error("Quantifiers cannot be used in lookarounds");
+        }
     }
 
     ParsedRegex m_parsed_regex;
@@ -679,15 +684,27 @@ private:
         return res;
     }
 
-    uint32_t push_lookaround(const Vector<ParsedRegex::AstNodePtr>& literals, bool reversed = false)
+    uint32_t push_lookaround(const Vector<ParsedRegex::AstNodePtr>& characters, bool reversed = false)
     {
         uint32_t res = m_program.lookarounds.size();
+        auto write_lookaround = [this](auto&& characters) {
+            for (auto& character : characters) 
+            {
+                if (character->op == ParsedRegex::Literal)
+                    m_program.lookarounds.push_back(character->value);
+                else if (character->op == ParsedRegex::AnyChar)
+                    m_program.lookarounds.push_back(0xF000);
+                else if (character->op == ParsedRegex::Matcher)
+                    m_program.lookarounds.push_back(0xF0001 + character->value);
+                else
+                    kak_assert(false);
+            }
+        };
+
         if (reversed)
-            for (auto& literal : literals | reverse()) 
-                m_program.lookarounds.push_back(literal->value);
+            write_lookaround(characters | reverse());
         else
-            for (auto& literal : literals) 
-                m_program.lookarounds.push_back(literal->value);
+            write_lookaround(characters);
 
         m_program.lookarounds.push_back((Codepoint)-1);
         return res;
diff --git a/src/regex_impl.hh b/src/regex_impl.hh
index 3addb2b2..cb5a53be 100644
--- a/src/regex_impl.hh
+++ b/src/regex_impl.hh
@@ -294,28 +294,14 @@ private:
                     break;
                 case CompiledRegex::LookAhead:
                 case CompiledRegex::NegativeLookAhead:
-                {
-                    auto ref = m_program.lookarounds.begin() + inst.param;
-                    for (auto it = pos; *ref != -1 and it != m_end; ++it, ++ref)
-                        if (*it != *ref)
-                            break;
-                    if ((inst.op == CompiledRegex::LookAhead and *ref != -1) or
-                        (inst.op == CompiledRegex::NegativeLookAhead and *ref == -1))
+                    if (lookaround<MatchDirection::Forward>(inst.param, pos) != (inst.op == CompiledRegex::LookAhead))
                         return StepResult::Failed;
                     break;
-                }
                 case CompiledRegex::LookBehind:
                 case CompiledRegex::NegativeLookBehind:
-                {
-                    auto ref = m_program.lookarounds.begin() + inst.param;
-                    for (auto it = pos; *ref != -1 and it > m_begin; --it, ++ref)
-                        if (*(it-1) != *ref)
-                            break;
-                    if ((inst.op == CompiledRegex::LookBehind and *ref != -1) or
-                        (inst.op == CompiledRegex::NegativeLookBehind and *ref == -1))
+                    if (lookaround<MatchDirection::Backward>(inst.param, pos) != (inst.op == CompiledRegex::LookBehind))
                         return StepResult::Failed;
                     break;
-                }
                 case CompiledRegex::Match:
                     return StepResult::Matched;
             }
@@ -392,6 +378,26 @@ private:
             ++start;
     }
 
+    template<MatchDirection look_direction>
+    bool lookaround(uint32_t index, Utf8It pos) const
+    {
+        for (auto it = m_program.lookarounds.begin() + index; *it != -1; ++it)
+        {
+            if (pos == (look_direction == MatchDirection::Forward ? m_end : m_begin))
+                return false;
+            auto cp = (look_direction == MatchDirection::Forward ? *pos : *(pos-1)), ref = *it;
+            if (ref == 0xF000)
+            {} // any character matches
+            else if (ref > 0xF0000 and ref <= 0xFFFFD and not m_program.matchers[ref - 0xF0001](cp))
+                return false;
+            else if (ref != cp)
+                return false;
+
+            (look_direction == MatchDirection::Forward) ? ++pos : --pos;
+        }
+        return true;
+    }
+
     bool is_line_start(const Utf8It& pos) const
     {
         if (not (m_flags & RegexExecFlags::PrevAvailable) and pos == m_begin)