diff --git a/README.md b/README.md
index 6db4ba6..12e917c 100644
--- a/README.md
+++ b/README.md
@@ -77,6 +77,14 @@ You can provide your own word list too (Note: the word list must meet [these ass
 toipe -f /path/to/word/list
 ```
 
+## Add punctuation to test
+
+By default, only lowercase words are shown. To add punctuation and sentence case, use the `-p` flag:
+
+```
+toipe -p
+```
+
 # Platform support
 
 - toipe was only tested on Linux and Mac OS. If you find any problems, please [open an issue](https://github.com/Samyak2/toipe/issues).
diff --git a/src/config.rs b/src/config.rs
index 957e693..2ea82df 100644
--- a/src/config.rs
+++ b/src/config.rs
@@ -30,6 +30,9 @@ pub struct ToipeConfig {
     /// Number of words to show on each test.
     #[clap(short, long, default_value_t = 30)]
     pub num_words: usize,
+    /// Whether to include punctuation
+    #[clap(short, long)]
+    pub punctuation: bool,
 }
 
 impl ToipeConfig {
diff --git a/src/lib.rs b/src/lib.rs
index 77458c5..553994a 100644
--- a/src/lib.rs
+++ b/src/lib.rs
@@ -24,7 +24,7 @@ use config::ToipeConfig;
 use results::ToipeResults;
 use termion::input::Keys;
 use termion::{color, event::Key, input::TermRead};
-use textgen::{RawWordSelector, WordSelector};
+use textgen::{PunctuatedWordSelector, RawWordSelector, WordSelector};
 use tui::{Text, ToipeTui};
 use wordlists::{BuiltInWordlist, OS_WORDLIST_PATH};
 
@@ -76,7 +76,7 @@ impl<'a> Toipe {
     /// Initializes the word selector.
     /// Also invokes [`Toipe::restart()`].
     pub fn new(config: ToipeConfig) -> Result<Self> {
-        let word_selector: Box<dyn WordSelector> = if let Some(wordlist_path) =
+        let mut word_selector: Box<dyn WordSelector> = if let Some(wordlist_path) =
             config.wordlist_file.clone()
         {
             Box::new(
@@ -105,6 +105,13 @@ impl<'a> Toipe {
             return Err(ToipeError::from("Undefined word list or path.".to_owned()))?;
         };
 
+        if config.punctuation {
+            word_selector = Box::new(PunctuatedWordSelector::from_word_selector(
+                word_selector,
+                0.15,
+            ))
+        }
+
         let mut toipe = Toipe {
             tui: ToipeTui::new(),
             words: Vec::new(),
diff --git a/src/textgen.rs b/src/textgen.rs
index 385d9f6..e6e67e6 100644
--- a/src/textgen.rs
+++ b/src/textgen.rs
@@ -1,10 +1,12 @@
 //! Utilities for generating/selecting new (random) words for the typing
 //! test.
 
+use std::collections::VecDeque;
 use std::fs::File;
 use std::io::{self, BufRead, BufReader, Cursor, Seek, SeekFrom};
 use std::path::PathBuf;
 
+use rand::seq::SliceRandom;
 use rand::Rng;
 
 use bisection::bisect_right;
@@ -248,3 +250,91 @@ impl<T: Seek + io::Read> WordSelector for RawWordSelector<T> {
         Ok(word)
     }
 }
+
+/// Wraps another word selector, taking words from it and adding punctuation to the end of or
+/// around words with a configurable chance. Will capitalize the next word when an end-of-sentence
+/// punctuation mark is used.
+pub struct PunctuatedWordSelector {
+    selector: Box<dyn WordSelector>,
+    next_is_capital: bool,
+    punctuation_chance: f64,
+}
+
+enum PunctuationType {
+    Capitaizing(char),
+    Ending(char),
+    Surrounding(char, char),
+}
+
+const PUNCTUATION: [PunctuationType; 12] = [
+    PunctuationType::Capitaizing('!'),
+    PunctuationType::Capitaizing('?'),
+    PunctuationType::Capitaizing('.'),
+    PunctuationType::Ending(','),
+    PunctuationType::Ending(':'),
+    PunctuationType::Ending(';'),
+    PunctuationType::Surrounding('\'', '\''),
+    PunctuationType::Surrounding('"', '"'),
+    PunctuationType::Surrounding('(', ')'),
+    PunctuationType::Surrounding('{', '}'),
+    PunctuationType::Surrounding('<', '>'),
+    PunctuationType::Surrounding('[', ']'),
+];
+
+impl PunctuatedWordSelector {
+    /// Creates a PunctuatedWordSelector from another WordSelector, allowing the selection of the
+    /// chance of punctuation.
+    pub fn from_word_selector(
+        word_selector: Box<dyn WordSelector>,
+        punctuation_chance: f64,
+    ) -> Self {
+        Self {
+            selector: word_selector,
+            next_is_capital: true,
+            punctuation_chance,
+        }
+    }
+}
+
+impl WordSelector for PunctuatedWordSelector {
+    fn new_word(&mut self) -> Result<String, io::Error> {
+        let mut rng = rand::thread_rng();
+
+        let mut word = self.selector.new_word()?;
+
+        let will_punctuate = rng.gen_bool(self.punctuation_chance);
+        if will_punctuate || self.next_is_capital {
+            let mut chars: VecDeque<char> = word.chars().collect();
+            if self.next_is_capital {
+                // some unicode chars map to multiple chars when uppercased.
+                for c in chars
+                    .pop_front()
+                    .expect("got empty word")
+                    .to_uppercase()
+                    .rev()
+                {
+                    chars.push_front(c)
+                }
+                self.next_is_capital = false;
+            }
+            if will_punctuate {
+                match PUNCTUATION
+                    .choose(&mut rng)
+                    .expect("only returns none if the slice is empty")
+                {
+                    PunctuationType::Capitaizing(c) => {
+                        self.next_is_capital = true;
+                        chars.push_back(*c)
+                    }
+                    PunctuationType::Ending(c) => chars.push_back(*c),
+                    PunctuationType::Surrounding(opening, closing) => {
+                        chars.push_front(*opening);
+                        chars.push_back(*closing);
+                    }
+                }
+            }
+            word = chars.into_iter().collect();
+        }
+        Ok(word)
+    }
+}