diff --git a/post.sh b/post.sh
index 4f2ef98..f7bc409 100755
--- a/post.sh
+++ b/post.sh
@@ -46,13 +46,23 @@ if [ -z ${FNAME} ]; then
     FNAME="./config/quotes"
 fi
 
-! test -s "${FNAME}" && find "./src" -type f -iname "*.txt" | shuf >"${FNAME}"
+function shift_list() {
+    ! test -s "${FNAME}" && find "./src" -type f -iname "*.txt" | shuf >"${FNAME}"
 
-QUOTE_FNAME=$(head -1 "${FNAME}")
-tail -n +2 "${FNAME}" > "${FNAME}.tmp" && mv "${FNAME}.tmp" "${FNAME}"
+    QUOTE_FNAME=$(head -1 "${FNAME}")
+    tail -n +2 "${FNAME}" > "${FNAME}.tmp" && mv "${FNAME}.tmp" "${FNAME}"
+}
 
-if [ ${TWEETMODE} ]; then
+function post_tweet() {
     ./util/tweet.py -c "${CREDENTIALS}" send -f "${QUOTE_FNAME}"
+    return $?
+}
+
+shift_list
+
+if [ ${TWEETMODE} ]; then
+    # Keep going until a tweet was posted
+    while post_tweet; [ $? -ne 0 ]; do shift_list; done
 else
     cat ${QUOTE_FNAME}
 fi
diff --git a/util/tweet.py b/util/tweet.py
index 2e72eb7..0f54f20 100755
--- a/util/tweet.py
+++ b/util/tweet.py
@@ -72,11 +72,14 @@ else:
         print("[ERROR]: Could not read from file.")
         logger.error(f"[{get_time_fmt()}] Could not read from file: {tweet_filename}; " +
                 os.strerror(e.errno))
+        sys.exit(1)
     else:
         if len(tweet_text) <= 280:
             api.update_status(tweet_text)
+            sys.exit(0)
         else:
             print("[ERROR]: Tweet text too long!")
             logger.error(f"[{get_time_fmt()}] Tweet contents too long; argument length: " +
                     f"{len(tweet_text)}; file location: {args.tweet_filename}")
+            sys.exit(1)