diff --git a/triggers/wordtrack/categories.sh b/triggers/wordtrack/categories.sh
index 37d049b..048011c 100644
--- a/triggers/wordtrack/categories.sh
+++ b/triggers/wordtrack/categories.sh
@@ -5,7 +5,8 @@
 
 # Category: coffee
 # Words that trigger tracking for coffee category
-coffeeWords=("coffee" "espresso" "latte" "mocha" "cappuccino" "americano" "frappuccino" "macchiato" "cortado" "affogato")
+# Note: coffee* allows matching at start of words (coffeehouse, coffeepot, etc.)
+coffeeWords=("coffee*" "espresso" "latte" "mocha" "cappuccino" "americano" "frappuccino" "macchiato" "cortado" "affogato")
 
 # Level thresholds and reward names for coffee category
 # Array key is the threshold (word count needed), value is the level name
@@ -30,7 +31,9 @@ declare -A teaLevels=(
 )
 
 # Category: gaming
-gamingWords=("game" "gaming" "play" "played" "console" "steam" "xbox" "playstation" "nintendo" "pc gaming")
+# Note: *game* matches game, gaming, endgame, videogame, etc.
+# Note: *play* matches play, played, playing, replay, gameplay, etc.
+gamingWords=("*game*" "*play*" "console" "steam" "xbox" "playstation" "nintendo" "pc gaming")
 
 declare -A gamingLevels=(
     [10]="Casual Gamer"
@@ -42,7 +45,7 @@ declare -A gamingLevels=(
 )
 
 # Words that trigger tracking for drugs category
-drugsWords=("kratom" "gummy" "hemp" "nicotine")
+drugsWords=("kratom" "gummy" "hemp" "nicotine" "vape")
 
 # Level thresholds and reward names for drugs category
 # Array key is the threshold (word count needed), value is the level name
diff --git a/triggers/wordtrack/wordtrack.sh b/triggers/wordtrack/wordtrack.sh
index 4afc941..40b9933 100755
--- a/triggers/wordtrack/wordtrack.sh
+++ b/triggers/wordtrack/wordtrack.sh
@@ -69,10 +69,48 @@ for category in "${categories[@]}"; do
         # Count all occurrences of this word in the message
         wordLower="${word,,}"
         tempMessage="$messageLower"
-        while [[ "$tempMessage" =~ $wordLower ]]; do
+
+        # Parse wildcard markers to determine match type
+        # * prefix = allow match at end of larger word (e.g., *game matches endgame)
+        # * suffix = allow match at start of larger word (e.g., coffee* matches coffeehouse)
+        # both = allow match anywhere (e.g., *play* matches gameplay)
+        # none = exact word match only (e.g., tea only matches tea)
+
+        prefixWild=false
+        suffixWild=false
+
+        if [[ "$wordLower" == \** ]]; then
+            prefixWild=true
+            wordLower="${wordLower#\*}"
+        fi
+
+        if [[ "$wordLower" == *\* ]]; then
+            suffixWild=true
+            wordLower="${wordLower%\*}"
+        fi
+
+        # Build regex pattern based on wildcard markers
+        if $prefixWild && $suffixWild; then
+            # Match anywhere in text
+            pattern="$wordLower"
+        elif $prefixWild; then
+            # Match at end of word or standalone
+            pattern="$wordLower([[:space:][:punct:]]|$)"
+        elif $suffixWild; then
+            # Match at start of word or standalone
+            pattern="(^|[[:space:][:punct:]])$wordLower"
+        else
+            # Exact word match only
+            pattern="(^|[[:space:][:punct:]])$wordLower([[:space:][:punct:]]|$)"
+        fi
+
+        # Use word boundary matching based on pattern
+        while [[ "$tempMessage" =~ $pattern ]]; do
             ((wordCount++))
             # Remove the matched word to find more occurrences
-            tempMessage="${tempMessage/$wordLower/}"
+            # Use the actual matched portion to avoid removing partial matches
+            matchedWord="${BASH_REMATCH[0]}"
+            tempMessage="${tempMessage/"$matchedWord"/ }"
         done
     done