diff --git a/Source/relay/TourGuide/Items of the Month/2023/SIT Course Certificate.ash b/Source/relay/TourGuide/Items of the Month/2023/SIT Course Certificate.ash
index f6a70d92..3ba4b411 100644
--- a/Source/relay/TourGuide/Items of the Month/2023/SIT Course Certificate.ash	
+++ b/Source/relay/TourGuide/Items of the Month/2023/SIT Course Certificate.ash	
@@ -14,12 +14,20 @@ void IOTMSITCertificateGenerateTasks(ChecklistEntry [int] task_entries, Checklis
     if (!lookupItem("S.I.T. Course Completion Certificate").have())
         return;
 
-    // Nag if we haven't picked a skill during this ascension    
+    boolean completedSITToday = get_property_boolean("_sitCourseCompleted");
+
+    // Nag if we haven't picked a skill during this ascension. Adding a daycount
+    //   piece to the nag that ensures this shows up on D2, prompting users to
+    //   change out their skill on D2. Not prompting on D3 or later, because
+    //   there's really only two good ones.
     string [int] skillNames = {"Psychogeologist", "Insectologist", "Cryptobotanist"};
-    if (hasAnySkillOf(skillNames)) {
+    if (hasAnySkillOf(skillNames) && my_daycount() >= 3) {
         return;
     }
 
+    // Don't generate a tile if the user has completed SIT already today
+    if (completedSITToday) return;
+
     string [int] description;
     string url = "inv_use.php?pwd=" + my_hash() + "&which=3&whichitem=11116";
     string main_title = "S.I.T. Course Enrollment";
@@ -28,8 +36,21 @@ void IOTMSITCertificateGenerateTasks(ChecklistEntry [int] task_entries, Checklis
         "Don't play hooky!",
         "You already paid for it.",
         "This one time in college...",
+        "Bright college days, oh, carefree days that fly.", // <3 tom lehrer
+        "No child of mine is leaving here without a degree!",
+        "Make like a tree and leaf (through your papers)",
     };
+
     string miscPhrase = miscPhrases[random(count(miscPhrases))];
     description.listAppend(HTMLGenerateSpanFont(miscPhrase + " Take your S.I.T. course!", "red"));
-    task_entries.listAppend(ChecklistEntryMake("__item S.I.T. Course Completion Certificate", url, ChecklistSubentryMake(main_title, description), -11).ChecklistEntrySetIDTag("S.I.T. Course Completion Certificate"));
+
+    string subtitle = "";
+
+    if (hasAnySkillOf(skillNames)) {
+        if (lookupSkill("Psychogeologist").have_skill())    subtitle = "you have ML; consider <b>Insectology</b>, for meat?";
+        if (lookupSkill("Insectologist").have_skill())      subtitle = "you have Meat; consider <b>Psychogeology</b>, for ML?";
+        if (lookupSkill("Cryptobotanist").have_skill())     subtitle = "you have Init; consider <b>Insectology</b>, for meat?";
+    }
+
+    task_entries.listAppend(ChecklistEntryMake("__item S.I.T. Course Completion Certificate", url, ChecklistSubentryMake(main_title, subtitle, description), -11).ChecklistEntrySetIDTag("S.I.T. Course Completion Certificate"));
 }