diff --git a/src/app/events/event_types/event/handlers/input.rs b/src/app/events/event_types/event/handlers/input.rs
index a4b72b6..ce9bbad 100644
--- a/src/app/events/event_types/event/handlers/input.rs
+++ b/src/app/events/event_types/event/handlers/input.rs
@@ -12,6 +12,7 @@ use crate::app::{
 
 pub async fn handle(app: &mut App<'_>, input_event: &CrosstermEvent) -> Result<EventStatus> {
     async fn default(converted_key: Key, app: &mut App<'_>, old_state: &State) -> Result<()> {
+        info!("No keymaps exist for key ('{}'), passing it along..", converted_key);
         // Just let the input event slip through if no keymap matches
         app.tx
             .send(Event::CommandEvent(
diff --git a/src/app/keymappings/key/key.rs b/src/app/keymappings/key/key.rs
index 74f06cb..f56609a 100644
--- a/src/app/keymappings/key/key.rs
+++ b/src/app/keymappings/key/key.rs
@@ -1,7 +1,8 @@
-use std::{str::FromStr, fmt::Display};
+use std::{fmt::Display, str::FromStr};
 
 use anyhow::{bail, Context};
-use crossterm::event::{Event, KeyEvent, KeyEventKind, KeyEventState, KeyModifiers};
+use cli_log::{debug, info};
+use crossterm::event::{Event, KeyCode, KeyEvent, KeyEventKind, KeyEventState, KeyModifiers};
 
 use super::{Chars, KeyValue, Keys};
 
@@ -236,7 +237,33 @@ impl Into<Event> for Key {
         }
 
         let output = Event::Key(KeyEvent {
-            code: self.value.unwrap_or(KeyValue::Null).into(),
+            code: {
+                // We sorta hit a edge case here, if we have a shifted char we need to tell
+                // crossterm about that. Thus we need to manually apply the shift modifier on the
+                // value.
+                if self.shift {
+                    if let Some(KeyValue::Char(char)) = self.value {
+                        let upper_case_char: char = {
+                            let chars = char.to_uppercase().collect::<Vec<char>>();
+                            if chars.len() != 1 {
+                                unimplemented!(
+                                    "
+                                    I have no idea how we handle this case,
+                                    we'll just have to hope, that it never comes up.
+                                    "
+                                );
+                            } else {
+                                *chars.first().expect("We checked the length")
+                            }
+                        };
+                        KeyCode::Char(upper_case_char)
+                    } else {
+                        self.value.unwrap_or(KeyValue::Null).into()
+                    }
+                } else {
+                    self.value.unwrap_or(KeyValue::Null).into()
+                }
+            },
             modifiers,
             kind: KeyEventKind::Press,
             state: KeyEventState::NONE,
@@ -266,7 +293,40 @@ impl TryFrom<&Event> for Key {
 
                 {
                     let key_code = key_event.code;
-                    output_key.value = Some(key_code.into());
+                    if output_key.shift {
+                        // We need to deal have an edge case for shift, as the value will be in the
+                        // shifted form (for example 'A'). If we left that, we would get "<S-A>" as
+                        // Key representation, which can't be parsed. So we simply unshift the 'A'
+                        // here, turning the representation into: "<S-a>"
+                        if let KeyCode::Char(char) = key_code {
+                            let lower_case_char: char = {
+                                let chars = char.to_lowercase().collect::<Vec<char>>();
+                                if chars.len() != 1 {
+                                    unimplemented!(
+                                        "
+                                    I have no idea how we handle this case,
+                                    we'll just have to hope, that it never comes up.
+                                    "
+                                    );
+                                } else {
+                                    *chars.first().expect("We checked the length")
+                                }
+                            };
+                            info!(
+                                "Had to translate key ('{}') to it's lowercase variant ('{}')",
+                                char, lower_case_char
+                            );
+                            output_key.value = Some(KeyValue::Char(lower_case_char));
+                        } else {
+                            debug!(
+                                "Key ('{}') is shifted but not a character!",
+                                Into::<KeyValue>::into(key_code)
+                            );
+                            output_key.value = Some(key_code.into());
+                        }
+                    } else {
+                        output_key.value = Some(key_code.into());
+                    }
                 }
 
                 Ok(output_key)
diff --git a/src/app/keymappings/key/mod.rs b/src/app/keymappings/key/mod.rs
index 97806e6..4a02938 100644
--- a/src/app/keymappings/key/mod.rs
+++ b/src/app/keymappings/key/mod.rs
@@ -45,6 +45,21 @@ mod test {
         )
     }
 
+    #[test]
+    fn test_shift_a() {
+        let keys: Keys = "<S-a>".parse().unwrap();
+        assert_eq!(
+            keys,
+            Keys(vec![Key {
+                alt: false,
+                ctrl: false,
+                meta: false,
+                shift: true,
+                value: Some(KeyValue::Char('a'))
+            }])
+        )
+    }
+
     #[test]
     fn test_string_repr() {
         let key = Key {