diff --git a/src/g_game.c b/src/g_game.c
index 3474d6ca9..ad519524d 100644
--- a/src/g_game.c
+++ b/src/g_game.c
@@ -4390,12 +4390,15 @@ void G_LoadGameSettings(void)
 #define GD_VERSIONCHECK 0xBA5ED123 // Change every major version, as usual
 #define GD_VERSIONMINOR 7 // Change every format update
 
+// You can't rearrange these without a special format update
 typedef enum
 {
 	GDEVER_ADDON = 1,
 	GDEVER_CREDITS = 1<<1,
 	GDEVER_REPLAY = 1<<2,
 	GDEVER_SPECIAL = 1<<3,
+	GDEVER_KEYTUTORIAL = 1<<4,
+	GDEVER_KEYMAJORSKIP = 1<<5,
 } gdeverdone_t;
 
 static const char *G_GameDataFolder(void)
@@ -4528,6 +4531,8 @@ void G_LoadGameData(void)
 			gamedata->everfinishedcredits = !!(everflags & GDEVER_CREDITS);
 			gamedata->eversavedreplay = !!(everflags & GDEVER_REPLAY);
 			gamedata->everseenspecial = !!(everflags & GDEVER_SPECIAL);
+			gamedata->chaokeytutorial = !!(everflags & GDEVER_KEYTUTORIAL);
+			gamedata->majorkeyskipattempted = !!(everflags & GDEVER_KEYMAJORSKIP);
 		}
 		else
 		{
@@ -5206,6 +5211,10 @@ void G_SaveGameData(void)
 			everflags |= GDEVER_REPLAY;
 		if (gamedata->everseenspecial)
 			everflags |= GDEVER_SPECIAL;
+		if (gamedata->chaokeytutorial)
+			everflags |= GDEVER_KEYTUTORIAL;
+		if (gamedata->majorkeyskipattempted)
+			everflags |= GDEVER_KEYMAJORSKIP;
 
 		WRITEUINT32(save.p, everflags); // 4
 	}
diff --git a/src/k_menu.h b/src/k_menu.h
index c6cda78d6..b154332be 100644
--- a/src/k_menu.h
+++ b/src/k_menu.h
@@ -1259,7 +1259,7 @@ extern struct challengesmenu_s {
 	boolean pending;
 	boolean requestnew;
 
-	boolean chaokeyadd;
+	boolean chaokeyadd, keywasadded;
 	UINT8 chaokeyhold;
 
 	boolean requestflip;
diff --git a/src/k_menudraw.c b/src/k_menudraw.c
index 681be183a..19c0815a3 100644
--- a/src/k_menudraw.c
+++ b/src/k_menudraw.c
@@ -5914,7 +5914,7 @@ static void M_DrawChallengeKeys(INT32 tilex, INT32 tiley)
 		24 << FRACBITS,
 		16 << FRACBITS,
 		0, kp_button_c[1],
-		M_MenuExtraHeld(pid)
+		menumessage.active == false && M_MenuExtraHeld(pid) == true
 	);
 
 	// Metyr of rounds played that contribute to Chao Key generation
diff --git a/src/m_cond.c b/src/m_cond.c
index 90faf6298..38bebcc28 100644
--- a/src/m_cond.c
+++ b/src/m_cond.c
@@ -658,6 +658,8 @@ void M_ClearStats(void)
 	gamedata->eversavedreplay = false;
 	gamedata->everseenspecial = false;
 	gamedata->evercrashed = false;
+	gamedata->chaokeytutorial = false;
+	gamedata->majorkeyskipattempted = false;
 	gamedata->musicstate = GDMUSIC_NONE;
 
 	gamedata->importprofilewins = false;
diff --git a/src/m_cond.h b/src/m_cond.h
index fb4d00195..b34ea5e0f 100644
--- a/src/m_cond.h
+++ b/src/m_cond.h
@@ -311,6 +311,8 @@ struct gamedata_t
 	boolean eversavedreplay;
 	boolean everseenspecial;
 	boolean evercrashed;
+	boolean chaokeytutorial;
+	boolean majorkeyskipattempted;
 	gdmusic_t musicstate;
 
 	// BACKWARDS COMPAT ASSIST
diff --git a/src/menus/extras-challenges.c b/src/menus/extras-challenges.c
index c0cd98b2e..779838056 100644
--- a/src/menus/extras-challenges.c
+++ b/src/menus/extras-challenges.c
@@ -308,6 +308,7 @@ menu_t *M_InterruptMenuWithChallenges(menu_t *desiredmenu)
 		challengesmenu.requestflip = false;
 		challengesmenu.requestnew = false;
 		challengesmenu.chaokeyadd = false;
+		challengesmenu.keywasadded = false;
 		challengesmenu.chaokeyhold = 0;
 		challengesmenu.currentunlock = MAXUNLOCKABLES;
 		challengesmenu.unlockcondition = NULL;
@@ -392,6 +393,55 @@ static boolean M_CanKeyHiliTile(void)
 	return true;
 }
 
+enum {
+	CCTUTORIAL_KEYGEN = 0,
+	CCTUTORIAL_MAJORSKIP,
+} cctutorial_e;
+
+static void M_ChallengesTutorial(UINT8 option)
+{
+	switch (option)
+	{
+		case CCTUTORIAL_KEYGEN:
+		{
+			M_StartMessage("Challenges & Chao Keys",
+				va(M_GetText(
+				"You just generated a Chao Key!\n"
+				"\n"
+				"They can be used to skip your way past\n"
+				"any Challenges you can see a hint for.\n"
+				"\n"
+				"But use them wisely - it'll take\n"
+				"%u rounds to pick up another.\n"
+				), GDCONVERT_ROUNDSTOKEY
+				), NULL, MM_NOTHING, NULL, NULL);
+			gamedata->chaokeytutorial = true;
+			break;
+		}
+		case CCTUTORIAL_MAJORSKIP:
+		{
+			M_StartMessage("Major Challenges & Chao Keys",
+				M_GetText(
+				"The larger tiles are Major Challenges.\n"
+				"They are significant tests of skill.\n"
+				"\n"
+				"If you're struggling and need to skip one,\n"
+				"not only will it cost you 10 Chao Keys, but\n"
+				"every nearby Challenge must be unlocked!\n"
+				), NULL, MM_NOTHING, NULL, "Wow, that's a lot");
+			gamedata->majorkeyskipattempted = true;
+			break;
+		}
+		default:
+		{
+			M_StartMessage("M_ChallengesTutorial ERROR",
+				"Invalid argument!?\n",
+				NULL, MM_NOTHING, NULL, NULL);
+			break;
+		}
+	}
+}
+
 void M_ChallengesTick(void)
 {
 	const UINT8 pid = 0;
@@ -536,6 +586,8 @@ void M_ChallengesTick(void)
 
 					if (gamedata->musicstate < GDMUSIC_KEYG)
 						gamedata->musicstate = GDMUSIC_KEYG;
+
+					challengesmenu.keywasadded = true;
 				}
 			}
 		}
@@ -652,6 +704,12 @@ void M_ChallengesTick(void)
 			{
 				// Play music the moment control returns.
 				M_PlayMenuJam();
+
+				if (gamedata->chaokeytutorial == false
+				&& challengesmenu.keywasadded == true)
+				{
+					M_ChallengesTutorial(CCTUTORIAL_KEYGEN);
+				}
 			}
 		}
 	}
@@ -671,7 +729,15 @@ boolean M_ChallengesInputs(INT32 ch)
 	}
 	else if (M_MenuExtraPressed(pid))
 	{
-		if (M_CanKeyHiliTile())
+		if (gamedata->chaokeytutorial == true
+			&& gamedata->majorkeyskipattempted == false
+			&& challengesmenu.currentunlock < MAXUNLOCKABLES
+			&& gamedata->unlocked[challengesmenu.currentunlock] == false
+			&& unlockables[challengesmenu.currentunlock].majorunlock == true)
+		{
+			M_ChallengesTutorial(CCTUTORIAL_MAJORSKIP);
+		}
+		else if (M_CanKeyHiliTile())
 		{
 			challengesmenu.chaokeyhold = 1;
 		}
@@ -696,6 +762,12 @@ boolean M_ChallengesInputs(INT32 ch)
 	{
 		gamedata->chaokeys++;
 		challengesmenu.unlockcount[CMC_CHAOANIM]++;
+
+		if (gamedata->chaokeytutorial == false)
+		{
+			M_ChallengesTutorial(CCTUTORIAL_KEYGEN);
+		}
+
 		S_StartSound(NULL, sfx_dbgsal);
 		return true;
 	}