diff --git a/src/cli.rs b/src/cli.rs
index be95100..851dc7b 100644
--- a/src/cli.rs
+++ b/src/cli.rs
@@ -13,7 +13,16 @@ pub struct CliArgs {
 pub enum Commands {
 	Init,
 	Untag(UntagArgs),
-	Tag(TagArgs),
+	Tag {
+		#[clap(flatten)]
+		args: TagArgs,
+
+		#[arg(short, long, requires = "file_tags", value_delimiter = ' ', num_args = 1..)]
+		files: Vec<PathBuf>,
+
+		#[arg(short('t'), long("tags"), requires = "files", value_delimiter = ' ', num_args = 1..)]
+		file_tags: Vec<String>,
+	},
 	Tags(TagsArgs),
 	Files(FilesArgs),
 }
@@ -31,13 +40,15 @@ pub enum TagsCommands {
 	List,
 	Add { add: Vec<String> },
 	Remove { remove: Vec<String> },
-	Rename { old: String, new: String },
+	Rename { renames: Vec<String> },
 }
 
 #[derive(Debug, Args, PartialEq, Eq)]
 pub struct TagArgs {
-	pub file: PathBuf,
+	// #[clap(conflicts_with = "files")]
+	pub file: Option<PathBuf>,
 
+	// #[clap(conflicts_with = "files")]
 	pub tags: Vec<String>,
 }
 
diff --git a/src/main.rs b/src/main.rs
index e71d03a..28a26ac 100644
--- a/src/main.rs
+++ b/src/main.rs
@@ -13,7 +13,11 @@ fn main() -> anyhow::Result<()> {
 
 	match args.commands {
 		cli::Commands::Init => init_db().map_err(|_| anyhow!("Database already exists!")),
-		cli::Commands::Tag(args) => tags::handle_tag(args),
+		cli::Commands::Tag {
+			args,
+			files,
+			file_tags,
+		} => tags::handle_tag(args, files, file_tags),
 		cli::Commands::Untag(args) => tags::handle_untag(args),
 		cli::Commands::Tags(args) => tags::handle_tags(args),
 		cli::Commands::Files(args) => tags::handle_files(args),
diff --git a/src/tags.rs b/src/tags.rs
index 5cb89fa..c732015 100644
--- a/src/tags.rs
+++ b/src/tags.rs
@@ -95,10 +95,17 @@ pub fn handle_files(args: FilesArgs) -> Result<()> {
 	Ok(())
 }
 
-pub fn handle_tag(args: TagArgs) -> Result<()> {
+pub fn handle_tag(args: TagArgs, files: Vec<PathBuf>, file_tags: Vec<String>) -> Result<()> {
 	let mut conn = try_database()?;
 
-	tag_file(&mut conn, args.file, args.tags)?;
+	if let Some(file) = args.file {
+		tag_file(&mut conn, &file, &args.tags)?;
+	} else {
+		// TODO: Maybe rework this at some point so its more optimized for batch insertion ?
+		for file in &files {
+			tag_file(&mut conn, file, &file_tags)?;
+		}
+	}
 
 	Ok(())
 }
@@ -130,14 +137,32 @@ pub fn handle_tags(args: TagsArgs) -> Result<()> {
 		}
 		Some(cli::TagsCommands::Add { add }) => add_tags(&mut conn, add),
 		Some(cli::TagsCommands::Remove { remove }) => remove_tags(&mut conn, remove),
-		Some(cli::TagsCommands::Rename { old, new }) => rename_tag(&conn, old, new),
+		Some(cli::TagsCommands::Rename { renames }) => rename_tag(&conn, renames),
 	}
 }
 
-fn rename_tag(conn: &Connection, old: String, new: String) -> Result<()> {
+fn rename_tag(conn: &Connection, renames: Vec<String>) -> Result<()> {
+	if renames.is_empty() {
+		return Err(anyhow!("No input found!"));
+	} else if renames.len() % 2 != 0 {
+		return Err(anyhow!(
+			"Attempting to rename an uneven amount of entries: {}",
+			renames.len()
+		));
+	}
+
 	let mut stmt = conn.prepare("UPDATE tag SET name = ? WHERE name = ?")?;
 
-	stmt.execute([&new, &old])?;
+	let mut i = 0;
+	while i < renames.len() {
+		// TODO: Merge this when let chaining is stabilized in 1.88
+		if let Some(old) = renames.get(i) {
+			if let Some(new) = renames.get(i + 1) {
+				stmt.execute([&new, &old])?;
+			}
+		}
+		i += 2;
+	}
 
 	Ok(())
 }
@@ -217,7 +242,7 @@ fn add_tags(conn: &mut Connection, tags: Vec<String>) -> Result<()> {
 	Ok(())
 }
 
-fn tag_file(conn: &mut Connection, file: PathBuf, tags: Vec<String>) -> Result<()> {
+fn tag_file(conn: &mut Connection, file: &PathBuf, tags: &Vec<String>) -> Result<()> {
 	let file = file
 		.to_str()
 		.ok_or(anyhow!("Unable to find path {:?}", file))?