diff --git a/include/cache.h b/include/cache.h
index 644a0b43..a9d53a98 100644
--- a/include/cache.h
+++ b/include/cache.h
@@ -44,7 +44,7 @@ void load_help(void);
 void send_user_motd(struct Client *);
 void send_user_rules(struct Client *);
 void send_oper_motd(struct Client *);
-void cache_user_motd(void);
+void cache_user_motd(struct Client *source_p);
 void cache_user_rules(void);
 
 struct Dictionary;
diff --git a/modules/m_rehash.c b/modules/m_rehash.c
index d8730d7e..589db509 100644
--- a/modules/m_rehash.c
+++ b/modules/m_rehash.c
@@ -86,13 +86,11 @@ rehash_dns(struct Client *source_p)
 static void
 rehash_ssld(struct Client *source_p)
 {
-    if (!IsOperAdmin(source_p)) {
-        sendto_one(source_p, form_str(ERR_NOPRIVS),
-                   me.name, source_p->name, "admin");
-        return;
-    }
-    sendto_realops_snomask(SNO_GENERAL, L_ALL, "%s is restarting ssld",
+    sendto_realops_snomask(SNO_GENERAL, L_NETWIDE,
+                           "%s is restarting ssld",
                            get_oper_name(source_p));
+    if (!MyConnect(source_p))
+        remote_rehash_oper_p = source_p;
 
     restart_ssld();
 }
@@ -100,42 +98,61 @@ rehash_ssld(struct Client *source_p)
 static void
 rehash_motd(struct Client *source_p)
 {
-    struct stat sb;
-    struct tm *local_tm;
-    
     sendto_realops_snomask(SNO_GENERAL, L_NETWIDE,
                            "%s is forcing re-reading of MOTD file",
                            get_oper_name(source_p));
     if (!MyConnect(source_p))
         remote_rehash_oper_p = source_p;
 
-    free_cachefile(user_motd);
-    user_motd = cache_file(MPATH, "ircd.motd", 0);
+    cache_user_motd(source_p);
+}
+
+static void
+rehash_rules(struct Client *source_p)
+{
+    struct cachefile *old_rules;
+    struct cachefile *new_rules;
     
-    if(stat(MPATH, &sb) == 0) {
-        local_tm = localtime(&sb.st_mtime);
-        
-        if(local_tm != NULL) {
-            rb_snprintf(user_motd_changed, sizeof(user_motd_changed),
-                        "%d/%d/%d %d:%d",
-                        local_tm->tm_mday, local_tm->tm_mon + 1,
-                        1900 + local_tm->tm_year, local_tm->tm_hour,
-                        local_tm->tm_min);
-        }
+    sendto_realops_snomask(SNO_GENERAL, L_NETWIDE,
+                           "%s is forcing re-reading of RULES file",
+                           get_oper_name(source_p));
+    if (!MyConnect(source_p))
+        remote_rehash_oper_p = source_p;
+
+    /* Load new cache first, then swap pointer, then free old cache.
+     * This prevents use-after-free if send_user_rules is iterating. */
+    new_rules = cache_file(RPATH, "ircd.rules", 0);
+    if(new_rules != NULL) {
+        /* Only update if new cache loaded successfully */
+        old_rules = user_rules;
+        user_rules = new_rules;
+        free_cachefile(old_rules);
     }
+    /* If new_rules is NULL (file missing/error), keep old RULES */
 }
 
 static void
 rehash_omotd(struct Client *source_p)
 {
+    struct cachefile *old_motd;
+    struct cachefile *new_motd;
+    
     sendto_realops_snomask(SNO_GENERAL, L_NETWIDE,
                            "%s is forcing re-reading of OPER MOTD file",
                            get_oper_name(source_p));
     if (!MyConnect(source_p))
         remote_rehash_oper_p = source_p;
 
-    free_cachefile(oper_motd);
-    oper_motd = cache_file(OPATH, "opers.motd", 0);
+    /* Load new cache first, then swap pointer, then free old cache.
+     * This prevents use-after-free if send_oper_motd is iterating. */
+    new_motd = cache_file(OPATH, "opers.motd", 0);
+    if(new_motd != NULL) {
+        /* Only update if new cache loaded successfully */
+        old_motd = oper_motd;
+        oper_motd = new_motd;
+        free_cachefile(old_motd);
+    }
+    /* If new_motd is NULL (file missing/error), keep old MOTD */
 }
 
 static void
diff --git a/src/cache.c b/src/cache.c
index 5ab83aff..73258f25 100644
--- a/src/cache.c
+++ b/src/cache.c
@@ -117,8 +117,11 @@ cache_file(const char *filename, const char *shortname, int flags)
     if((in = fopen(filename, "r")) == NULL)
         return NULL;
 
-
     cacheptr = rb_malloc(sizeof(struct cachefile));
+    if(cacheptr == NULL) {
+        fclose(in);
+        return NULL;
+    }
 
     rb_strlcpy(cacheptr->name, shortname, sizeof(cacheptr->name));
     cacheptr->flags = flags;
@@ -130,10 +133,26 @@ cache_file(const char *filename, const char *shortname, int flags)
 
         if(!EmptyString(line)) {
             lineptr = rb_malloc(sizeof(struct cacheline));
+            if(lineptr == NULL) {
+                /* Memory allocation failed - free what we have and abort */
+                free_cachefile(cacheptr);
+                fclose(in);
+                return NULL;
+            }
             untabify(lineptr->data, line, sizeof(lineptr->data));
             rb_dlinkAddTail(lineptr, &lineptr->linenode, &cacheptr->contents);
-        } else
-            rb_dlinkAddTailAlloc(emptyline, &cacheptr->contents);
+        } else {
+            /* Only add emptyline if it's initialized */
+            if(emptyline != NULL)
+                rb_dlinkAddTailAlloc(emptyline, &cacheptr->contents);
+        }
+    }
+
+    /* Check for read errors */
+    if(ferror(in)) {
+        free_cachefile(cacheptr);
+        fclose(in);
+        return NULL;
     }
 
     if (0 == rb_dlink_list_length(&cacheptr->contents)) {
@@ -199,7 +218,6 @@ free_cachefile(struct cachefile *cacheptr)
     RB_DLINK_FOREACH_SAFE(ptr, next_ptr, cacheptr->contents.head) {
         if(ptr->data != emptyline) {
             struct cacheline *line = ptr->data;
-            rb_free(line->data);
             rb_free(line);
         } else {
             rb_free_rb_dlink_node(ptr);
@@ -297,16 +315,22 @@ send_user_motd(struct Client *source_p)
 {
     struct cacheline *lineptr;
     rb_dlink_node *ptr;
+    rb_dlink_node *next_ptr;
+    struct cachefile *motd;
     const char *myname = get_id(&me, source_p);
     const char *nick = get_id(source_p, source_p);
-    if(user_motd == NULL || rb_dlink_list_length(&user_motd->contents) == 0) {
+    
+    /* Capture pointer locally to prevent use-after-free if rehash happens */
+    motd = user_motd;
+    if(motd == NULL || rb_dlink_list_length(&motd->contents) == 0) {
         sendto_one(source_p, form_str(ERR_NOMOTD), myname, nick);
         return;
     }
 
     sendto_one(source_p, form_str(RPL_MOTDSTART), myname, nick, me.name);
 
-    RB_DLINK_FOREACH(ptr, user_motd->contents.head) {
+    /* Use safe iterator to prevent crash if cache is freed during iteration */
+    RB_DLINK_FOREACH_SAFE(ptr, next_ptr, motd->contents.head) {
         lineptr = ptr->data;
         sendto_one(source_p, form_str(RPL_MOTD), myname, nick, lineptr->data);
     }
@@ -315,10 +339,13 @@ send_user_motd(struct Client *source_p)
 }
 
 void
-cache_user_motd(void)
+cache_user_motd(struct Client *source_p)
 {
     struct stat sb;
     struct tm *local_tm;
+    struct cachefile *old_motd;
+    struct cachefile *new_motd;
+    int save_errno;
 
     if(stat(MPATH, &sb) == 0) {
         local_tm = localtime(&sb.st_mtime);
@@ -331,8 +358,40 @@ cache_user_motd(void)
                         local_tm->tm_min);
         }
     }
-    free_cachefile(user_motd);
-    user_motd = cache_file(MPATH, "ircd.motd", 0);
+    /* Load new cache first, then swap pointer, then free old cache.
+     * This prevents use-after-free if send_user_motd is iterating. */
+    errno = 0;
+    new_motd = cache_file(MPATH, "ircd.motd", 0);
+    save_errno = errno;
+    
+    if(new_motd != NULL) {
+        /* Only update if new cache loaded successfully */
+        old_motd = user_motd;
+        user_motd = new_motd;
+        free_cachefile(old_motd);
+        
+        if(source_p != NULL) {
+            sendto_one_notice(source_p, ":*** Notice -- Successfully reloaded MOTD from %s", MPATH);
+        }
+    } else {
+        /* If new_motd is NULL (file missing/error), keep old MOTD */
+        if(source_p != NULL) {
+            if(save_errno != 0) {
+                if(save_errno == ENOENT) {
+                    sendto_one_notice(source_p, ":*** Notice -- Failed to reload MOTD from %s: File not found", MPATH);
+                } else if(save_errno == EACCES) {
+                    sendto_one_notice(source_p, ":*** Notice -- Failed to reload MOTD from %s: Permission denied", MPATH);
+                } else {
+                    sendto_one_notice(source_p, ":*** Notice -- Failed to reload MOTD from %s: %s (errno %d)", 
+                                      MPATH, strerror(save_errno), save_errno);
+                }
+            } else if(user_motd == NULL) {
+                sendto_one_notice(source_p, ":*** Notice -- Failed to reload MOTD from %s: File is empty or contains no valid lines", MPATH);
+            } else {
+                sendto_one_notice(source_p, ":*** Notice -- Failed to reload MOTD from %s: File read error or memory allocation failed (keeping old MOTD)", MPATH);
+            }
+        }
+    }
 }
 
 
@@ -347,14 +406,19 @@ send_oper_motd(struct Client *source_p)
 {
     struct cacheline *lineptr;
     rb_dlink_node *ptr;
+    rb_dlink_node *next_ptr;
+    struct cachefile *motd;
 
-    if(oper_motd == NULL || rb_dlink_list_length(&oper_motd->contents) == 0)
+    /* Capture pointer locally to prevent use-after-free if rehash happens */
+    motd = oper_motd;
+    if(motd == NULL || rb_dlink_list_length(&motd->contents) == 0)
         return;
 
     sendto_one(source_p, form_str(RPL_OMOTDSTART),
                me.name, source_p->name);
 
-    RB_DLINK_FOREACH(ptr, oper_motd->contents.head) {
+    /* Use safe iterator to prevent crash if cache is freed during iteration */
+    RB_DLINK_FOREACH_SAFE(ptr, next_ptr, motd->contents.head) {
         lineptr = ptr->data;
         sendto_one(source_p, form_str(RPL_OMOTD),
                    me.name, source_p->name, lineptr->data);
diff --git a/src/ircd.c b/src/ircd.c
index cdab3d9a..63ce122f 100644
--- a/src/ircd.c
+++ b/src/ircd.c
@@ -259,7 +259,7 @@ check_rehash(void *unused)
     if(doremotd) {
         sendto_realops_snomask(SNO_GENERAL, L_ALL,
                                "Got signal SIGUSR1, reloading ircd motd file");
-        cache_user_motd();
+        cache_user_motd(NULL);
         doremotd = 0;
     }
 }