diff --git a/src/api/server_server.rs b/src/api/server_server.rs
index 3ab5709c..58db059f 100644
--- a/src/api/server_server.rs
+++ b/src/api/server_server.rs
@@ -132,7 +132,9 @@ where
         ));
     }
 
-    if destination.is_ip_literal() {
+    // rust's built in <Ipv4Addr> parsing does not consider things like octal addresses valid
+    // so we should check both just to be safe.
+    if destination.is_ip_literal() || IPAddress::is_valid(destination.host()) {
         info!(
             "Destination {} is an IP literal, checking against IP range denylist.",
             destination
diff --git a/src/service/sending/mod.rs b/src/service/sending/mod.rs
index b05bef2b..3bf18aac 100644
--- a/src/service/sending/mod.rs
+++ b/src/service/sending/mod.rs
@@ -717,7 +717,9 @@ impl Service {
     where
         T: Debug,
     {
-        if destination.is_ip_literal() {
+        // rust's built in <Ipv4Addr> parsing does not consider things like octal addresses valid
+        // so we should check both just to be safe.
+        if destination.is_ip_literal() || IPAddress::is_valid(destination.host()) {
             info!(
                 "Destination {} is an IP literal, checking against IP range denylist.",
                 destination