diff --git a/public/_locales/en/messages.json b/public/_locales/en/messages.json
index b3b9e152..7a5dd69b 100644
--- a/public/_locales/en/messages.json
+++ b/public/_locales/en/messages.json
@@ -116,6 +116,9 @@
     "connectionError": {
         "message": "A connection error has occurred. Error code: "
     },
+    "segmentsStillLoading": {
+        "message": "Segments still loading..."
+    },
     "clearTimes": {
         "message": "Clear Segments"
     },
@@ -1243,5 +1246,8 @@
     },
     "exportSegmentsAsURL": {
         "message": "Share as URL"
+    },
+    "segmentFetchFailureWarning": {
+        "message": "Warning: The server hasn't responded with segments yet. There might actually be segments on this video already submitted but you just haven't recieved them due to issues with the server."
     }
 }
diff --git a/src/content.ts b/src/content.ts
index d9eb9a8c..3bfb66a5 100644
--- a/src/content.ts
+++ b/src/content.ts
@@ -56,6 +56,7 @@ let sponsorVideoID: VideoID = null;
 const skipNotices: SkipNotice[] = [];
 let activeSkipKeybindElement: ToggleSkippable = null;
 let retryFetchTimeout: NodeJS.Timeout = null;
+let shownSegmentFailedToFetchWarning = false;
 
 // JSON video info
 let videoInfo: VideoInfo = null;
@@ -344,6 +345,8 @@ function resetValues() {
     sponsorTimes = [];
     existingChaptersImported = false;
     sponsorSkipped = [];
+    lastResponseStatus = 0;
+    shownSegmentFailedToFetchWarning = false;
 
     sponsorVideoID = null;
     videoInfo = null;
@@ -1922,6 +1925,12 @@ function startOrEndTimingNewSegment() {
     updateSponsorTimesSubmitting(false);
 
     importExistingChapters(false);
+
+    if (lastResponseStatus !== 200 && !shownSegmentFailedToFetchWarning) {
+        alert(chrome.i18n.getMessage("segmentFetchFailureWarning"));
+
+        shownSegmentFailedToFetchWarning = true;
+    }
 }
 
 function getIncompleteSegment(): SponsorTime {
diff --git a/src/popup.ts b/src/popup.ts
index 400906a0..d2e763f4 100644
--- a/src/popup.ts
+++ b/src/popup.ts
@@ -456,7 +456,12 @@ async function runThePopup(messageListener?: MessageListener): Promise<void> {
                 PageElements.videoFound.innerHTML = chrome.i18n.getMessage("sponsor404");
                 PageElements.issueReporterImportExport.classList.remove("hidden");
             } else {
-                PageElements.videoFound.innerHTML = chrome.i18n.getMessage("connectionError") + request.status;
+                if (request.status) {
+                    PageElements.videoFound.innerHTML = chrome.i18n.getMessage("connectionError") + request.status;
+                } else {
+                    PageElements.videoFound.innerHTML = chrome.i18n.getMessage("segmentsStillLoading");
+                }
+                
                 PageElements.issueReporterImportExport.classList.remove("hidden");
             }
         }