diff --git a/include/data.h b/include/data.h
index 122833c3..1db7c442 100644
--- a/include/data.h
+++ b/include/data.h
@@ -148,7 +148,7 @@ struct Ignore_Event {
  *
  */
 struct regex {
-    const char *pattern;
+    char *pattern;
     pcre *regex;
     pcre_extra *extra;
 };
diff --git a/include/match.h b/include/match.h
index 2786c66a..6c0694ef 100644
--- a/include/match.h
+++ b/include/match.h
@@ -28,4 +28,10 @@ void match_copy(Match *dest, Match *src);
  */
 bool match_matches_window(Match *match, i3Window *window);
 
+/**
+ * Frees the given match. It must not be used afterwards!
+ *
+ */
+void match_free(Match *match);
+
 #endif
diff --git a/include/regex.h b/include/regex.h
index 2a6608a8..adfa6656 100644
--- a/include/regex.h
+++ b/include/regex.h
@@ -17,6 +17,12 @@
  */
 struct regex *regex_new(const char *pattern);
 
+/**
+ * Frees the given regular expression. It must not be used afterwards!
+ *
+ */
+void regex_free(struct regex *regex);
+
 /**
  * Checks if the given regular expression matches the given input and returns
  * true if it does. In either case, it logs the outcome using LOG(), so it will
diff --git a/src/config.c b/src/config.c
index 5dc52472..c979d8cd 100644
--- a/src/config.c
+++ b/src/config.c
@@ -280,15 +280,19 @@ void load_configuration(xcb_connection_t *conn, const char *override_configpath,
             SLIST_REMOVE(&modes, mode, Mode, modes);
         }
 
-#if 0
         struct Assignment *assign;
         while (!TAILQ_EMPTY(&assignments)) {
             assign = TAILQ_FIRST(&assignments);
-            FREE(assign->windowclass_title);
+            if (assign->type == A_TO_WORKSPACE)
+                FREE(assign->dest.workspace);
+            else if (assign->type == A_TO_OUTPUT)
+                FREE(assign->dest.output);
+            else if (assign->type == A_COMMAND)
+                FREE(assign->dest.command);
+            match_free(&(assign->match));
             TAILQ_REMOVE(&assignments, assign, assignments);
             FREE(assign);
         }
-#endif
 
         /* Clear workspace names */
 #if 0
diff --git a/src/match.c b/src/match.c
index 85d2eaab..3514acee 100644
--- a/src/match.c
+++ b/src/match.c
@@ -136,3 +136,23 @@ bool match_matches_window(Match *match, i3Window *window) {
 
     return true;
 }
+
+/*
+ * Frees the given match. It must not be used afterwards!
+ *
+ */
+void match_free(Match *match) {
+    /* First step: free the regex fields / patterns */
+    regex_free(match->title);
+    regex_free(match->application);
+    regex_free(match->class);
+    regex_free(match->instance);
+    regex_free(match->mark);
+
+    /* Second step: free the regex helper struct itself */
+    FREE(match->title);
+    FREE(match->application);
+    FREE(match->class);
+    FREE(match->instance);
+    FREE(match->mark);
+}
diff --git a/src/regex.c b/src/regex.c
index da8f91d8..f419e4bb 100644
--- a/src/regex.c
+++ b/src/regex.c
@@ -49,6 +49,18 @@ struct regex *regex_new(const char *pattern) {
     return re;
 }
 
+/*
+ * Frees the given regular expression. It must not be used afterwards!
+ *
+ */
+void regex_free(struct regex *regex) {
+    if (!regex)
+        return;
+    FREE(regex->pattern);
+    FREE(regex->regex);
+    FREE(regex->extra);
+}
+
 /*
  * Checks if the given regular expression matches the given input and returns
  * true if it does. In either case, it logs the outcome using LOG(), so it will