diff --git a/src/matcher/mod.rs b/src/matcher/mod.rs
index d511bd4..0f2f191 100644
--- a/src/matcher/mod.rs
+++ b/src/matcher/mod.rs
@@ -33,6 +33,7 @@ pub struct Match {
     pub content: MatchContentType,
     pub word: bool,
     pub passive_only: bool,
+    pub propagate_case: bool,
 
     // Automatically calculated from the triggers, used by the matcher to check for correspondences.
     #[serde(skip_serializing)]
@@ -74,7 +75,7 @@ impl<'a> From<&'a AutoMatch> for Match{
             static ref VAR_REGEX: Regex = Regex::new("\\{\\{\\s*(\\w+)\\s*\\}\\}").unwrap();
         };
 
-        let triggers = if !other.triggers.is_empty() {
+        let mut triggers = if !other.triggers.is_empty() {
             other.triggers.clone()
         }else if !other.trigger.is_empty() {
             vec!(other.trigger.clone())
@@ -82,6 +83,26 @@ impl<'a> From<&'a AutoMatch> for Match{
             panic!("Match does not have any trigger defined: {:?}", other)
         };
 
+        // If propagate_case is true, we need to generate all the possible triggers
+        // For example, specifying "hello" as a trigger, we need to have:
+        // "hello", "Hello", "HELLO"
+        if other.propagate_case {
+            // List with first letter capitalized
+            let first_capitalized : Vec<String> = triggers.iter().map(|trigger| {
+                let mut capitalized = trigger.clone();
+                let mut v: Vec<char> = capitalized.chars().collect();
+                v[0] = v[0].to_uppercase().nth(0).unwrap();
+                v.into_iter().collect()
+            }).collect();
+
+            let all_capitalized : Vec<String> = triggers.iter().map(|trigger| {
+                trigger.to_uppercase()
+            }).collect();
+
+            triggers.extend(first_capitalized);
+            triggers.extend(all_capitalized);
+        }
+
         let trigger_sequences = triggers.iter().map(|trigger| {
             // Calculate the trigger sequence
             let mut trigger_sequence = Vec::new();
@@ -148,6 +169,7 @@ impl<'a> From<&'a AutoMatch> for Match{
             word: other.word,
             passive_only: other.passive_only,
             _trigger_sequences: trigger_sequences,
+            propagate_case: other.propagate_case,
         }
     }
 }
@@ -175,6 +197,9 @@ struct AutoMatch {
 
     #[serde(default = "default_passive_only")]
     pub passive_only: bool,
+
+    #[serde(default = "default_propagate_case")]
+    pub propagate_case: bool,
 }
 
 fn default_trigger() -> String {"".to_owned()}
@@ -184,6 +209,7 @@ fn default_word() -> bool {false}
 fn default_passive_only() -> bool {false}
 fn default_replace() -> Option<String> {None}
 fn default_image_path() -> Option<String> {None}
+fn default_propagate_case() -> bool {false}
 
 #[derive(Debug, Serialize, Deserialize, Clone)]
 pub struct MatchVariable {
@@ -377,4 +403,60 @@ mod tests {
 
         assert_eq!(_match.triggers, vec![":test1", ":test2"])
     }
+
+    #[test]
+    fn test_match_propagate_case() {
+        let match_str = r###"
+        trigger: "hello"
+        replace: "This is a test"
+        propagate_case: true
+        "###;
+
+        let _match : Match = serde_yaml::from_str(match_str).unwrap();
+
+        assert_eq!(_match.triggers, vec!["hello", "Hello", "HELLO"])
+    }
+
+    #[test]
+    fn test_match_propagate_case_multi_trigger() {
+        let match_str = r###"
+        triggers: ["hello", "hi"]
+        replace: "This is a test"
+        propagate_case: true
+        "###;
+
+        let _match : Match = serde_yaml::from_str(match_str).unwrap();
+
+        assert_eq!(_match.triggers, vec!["hello", "hi", "Hello", "Hi", "HELLO", "HI"])
+    }
+
+    #[test]
+    fn test_match_trigger_sequence_with_word_propagate_case() {
+        let match_str = r###"
+        trigger: "test"
+        replace: "This is a test"
+        word: true
+        propagate_case: true
+        "###;
+
+        let _match : Match = serde_yaml::from_str(match_str).unwrap();
+
+        assert_eq!(_match._trigger_sequences[0][0], TriggerEntry::Char('t'));
+        assert_eq!(_match._trigger_sequences[0][1], TriggerEntry::Char('e'));
+        assert_eq!(_match._trigger_sequences[0][2], TriggerEntry::Char('s'));
+        assert_eq!(_match._trigger_sequences[0][3], TriggerEntry::Char('t'));
+        assert_eq!(_match._trigger_sequences[0][4], TriggerEntry::WordSeparator);
+
+        assert_eq!(_match._trigger_sequences[1][0], TriggerEntry::Char('T'));
+        assert_eq!(_match._trigger_sequences[1][1], TriggerEntry::Char('e'));
+        assert_eq!(_match._trigger_sequences[1][2], TriggerEntry::Char('s'));
+        assert_eq!(_match._trigger_sequences[1][3], TriggerEntry::Char('t'));
+        assert_eq!(_match._trigger_sequences[1][4], TriggerEntry::WordSeparator);
+
+        assert_eq!(_match._trigger_sequences[2][0], TriggerEntry::Char('T'));
+        assert_eq!(_match._trigger_sequences[2][1], TriggerEntry::Char('E'));
+        assert_eq!(_match._trigger_sequences[2][2], TriggerEntry::Char('S'));
+        assert_eq!(_match._trigger_sequences[2][3], TriggerEntry::Char('T'));
+        assert_eq!(_match._trigger_sequences[2][4], TriggerEntry::WordSeparator);
+    }
 }
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