diff --git a/src/controller/outbox.c b/src/controller/outbox.c
index 8ed59ae..ecc89e6 100644
--- a/src/controller/outbox.c
+++ b/src/controller/outbox.c
@@ -20,7 +20,7 @@
 #include <string.h>
 #include <unistd.h>
 
-static bool process_envelope( int id )
+static bool process_envelope( struct outbox_envelope* env )
 {
 	bool result = false;
 	char* postdata = NULL;
@@ -28,17 +28,10 @@ static bool process_envelope( int id )
 	FILE* f = NULL;
 	struct ap_activity* act = NULL;
 
-	// Get next outbox item
-	struct outbox_envelope* env = outbox_envelope_from_id( id );
-	if( !env ) {
-		printf( "? No envelope\n" );
-		goto failed;
-	}
-
 	if( env->sent ) { return false; }
 	if( env->retry_after > time(NULL) ) { return false; }
 
-	printf( "Processing outbox/%d.json\n", id );
+	printf( "Processing outbox/%d.json\n", env->id );
 	printf( "account_id=%d\n", env->account_id );
 	printf( "activity_id=%d\n", env->activity_id );
 
@@ -136,7 +129,6 @@ static bool process_envelope( int id )
 cleanup:
 	ap_activity_free(act);
 	account_free(to_account);
-	outbox_envelope_free(env);
 	free(postdata);
 
 	crypto_keys_free(keys);
@@ -157,10 +149,21 @@ static bool process_one()
 	int tail = fs_list_get("data/outbox/TAIL");
 	bool result = false;
 	for( int i = tail + 1; i <= head; ++i ) {
-		if( process_envelope(i) ) {
-			printf( "Done with outbox/%d.json\n", i );
-			result = true;
-			//fs_list_set( "data/outbox/TAIL", tail + 1 );
+		struct outbox_envelope* env = outbox_envelope_from_id( i );
+		if( !env ) {
+			// Envelope file doesn't exist, advance tail
+			fs_list_set( "data/outbox/TAIL", i );
+			tail += 1;
+		} else if( env ) {
+			if( env->sent && i == tail+1 ) {
+				// Envelope already sent, advance tail
+				fs_list_set( "data/outbox/TAIL", i );
+				tail += 1;
+			} else if( process_envelope(env) ) {
+				printf( "Done with outbox/%d.json\n", i );
+				result = true;
+			}
+			outbox_envelope_free(env);
 		}
 	}