diff --git a/src/subcommand/checkout_subcommand.cpp b/src/subcommand/checkout_subcommand.cpp
@@ -1,8 +1,10 @@
 #include "../subcommand/checkout_subcommand.hpp"
 
+#include <filesystem>
 #include <iostream>
 #include <set>
-#include <sstream>
+
+#include <git2/oid.h>
 
 #include "../subcommand/status_subcommand.hpp"
 #include "../utils/git_exception.hpp"
@@ -13,7 +15,10 @@ checkout_subcommand::checkout_subcommand(const libgit2_object&, CLI::App& app)
 {
     auto* sub = app.add_subcommand("checkout", "Switch branches or restore working tree files");
 
-    sub->add_option("<branch>", m_branch_name, "Branch to checkout");
+    // "-- file" lands in m_positional_args because CLI11 consumes "--" silently.
+    sub->add_option("<tree-ish|pathspec>", m_positional_args, "Tree-ish to checkout, and/or one/many pathspec(s)");
+    // checkout <branch>, checkout <tag>, checkout <file> ..., checkout <branch> <file> ...
+    // Use without "--"
     sub->add_flag("-b", m_create_flag, "Create a new branch before checking it out");
     sub->add_flag("-B", m_force_create_flag, "Create a new branch or reset it if it exists before checking it out");
     sub->add_flag(
@@ -51,6 +56,56 @@ namespace
     }
 }
 
+void checkout_subcommand::checkout_files(
+    const repository_wrapper& repo,
+    const std::vector<std::string>& files,
+    const git_checkout_options& base_options
+)
+{
+    std::vector<const char*> pathspec_strings;
+    pathspec_strings.reserve(files.size());
+    for (const auto& f : files)
+    {
+        pathspec_strings.push_back(f.c_str());
+    }
+
+    git_checkout_options options = base_options;
+    options.paths.strings = const_cast<char**>(pathspec_strings.data());
+    options.paths.count = pathspec_strings.size();
+
+    throw_if_error(git_checkout_head(repo, &options));
+}
+
+void checkout_subcommand::checkout_paths(
+    const repository_wrapper& repo,
+    const std::string_view tree_ish,
+    const std::vector<std::string>& pathspecs,
+    const git_checkout_options& base_options
+)
+{
+    auto obj = repo.revparse_single(tree_ish);
+    if (!obj)
+    {
+        throw git_exception(
+            "error: could not resolve tree-ish '" + std::string(tree_ish) + "'",
+            git2cpp_error_code::BAD_ARGUMENT
+        );
+    }
+
+    std::vector<const char*> pathspec_strings;
+    pathspec_strings.reserve(pathspecs.size());
+    for (const auto& p : pathspecs)
+    {
+        pathspec_strings.push_back(p.c_str());
+    }
+
+    git_checkout_options options = base_options;
+    options.paths.strings = const_cast<char**>(pathspec_strings.data());
+    options.paths.count = pathspec_strings.size();
+
+    throw_if_error(git_checkout_tree(repo, *obj, &options));
+}
+
 void checkout_subcommand::run()
 {
     auto directory = get_current_git_path();
@@ -73,57 +128,134 @@ void checkout_subcommand::run()
         options.checkout_strategy = GIT_CHECKOUT_SAFE;
     }
 
-    if (m_create_flag || m_force_create_flag)
+    if (m_positional_args.empty())
     {
-        auto annotated_commit = create_local_branch(repo, m_branch_name, m_force_create_flag);
-        checkout_tree(repo, annotated_commit, m_branch_name, options);
-        update_head(repo, annotated_commit, m_branch_name);
-
-        std::cout << "Switched to a new branch '" << m_branch_name << "'" << std::endl;
+        throw std::runtime_error("error: no branch or file specified");
     }
-    else
+
+    const std::string& target_name = m_positional_args[0];  // can be a branch or a tag
+    const std::vector<std::string> pathspecs(m_positional_args.begin() + 1, m_positional_args.end());
+
+    if (m_create_flag || m_force_create_flag)
     {
-        auto optional_commit = repo.resolve_local_ref(m_branch_name);
-        if (!optional_commit)
+        if (!pathspecs.empty())
         {
-            // TODO: handle remote refs
-            std::ostringstream buffer;
-            buffer << "error: could not resolve pathspec '" << m_branch_name << "'" << std::endl;
-            throw std::runtime_error(buffer.str());
+            throw git_exception("error: '-b' or '-B' does not accept pathspecs.", git2cpp_error_code::BAD_ARGUMENT);
         }
 
-        auto sl = status_list_wrapper::status_list(repo);
-        try
+        auto annotated_commit = create_local_branch(repo, target_name, m_force_create_flag);
+        checkout_tree(repo, annotated_commit, target_name, options);
+        update_head(repo, annotated_commit, target_name);
+
+        std::cout << "Switched to a new branch '" << target_name << "'" << std::endl;
+        return;
+    }
+
+    if (!pathspecs.empty())
+    {
+        // Try tree-ish + pathspec(s)
+        if (auto obj = repo.revparse_single(target_name))
         {
-            checkout_tree(repo, *optional_commit, m_branch_name, options);
-            update_head(repo, *optional_commit, m_branch_name);
+            // Validate all pathspecs before checkout so we can mimic git-like errors
+            for (const auto& p : pathspecs)
+            {
+                if (!std::filesystem::exists(std::filesystem::path(directory) / p) && !repo.does_track(p))
+                {
+                    throw git_exception(
+                        "error: pathspec '" + p + "' did not match any file(s) known to git",
+                        git2cpp_error_code::BAD_ARGUMENT
+                    );
+                }
+            }
+
+            options.checkout_strategy = GIT_CHECKOUT_FORCE;
+            checkout_paths(repo, target_name, pathspecs, options);
+            return;
         }
-        catch (const git_exception& e)
+
+        // Else treat as files
+        for (const auto& p : pathspecs)
         {
-            if (sl.has_notstagged_header())
+            if (!std::filesystem::exists(std::filesystem::path(directory) / p) && !repo.does_track(p))
             {
-                print_no_switch(sl);
+                throw git_exception(
+                    "error: pathspec '" + p + "' did not match any file(s) known to git",
+                    git2cpp_error_code::BAD_ARGUMENT
+                );
             }
-            throw e;
         }
 
-        if (sl.has_notstagged_header())
+        std::vector<std::string> files = m_positional_args;
+        options.checkout_strategy = GIT_CHECKOUT_FORCE;
+        checkout_files(repo, files, options);
+        return;
+    }
+
+    auto optional_commit = repo.resolve_local_ref(target_name);
+    if (!optional_commit)
+    {
+        // TODO: handle remote refs
+
+        // Fall back to checking out a unique file
+        const std::vector<std::string> file = {target_name};
+
+        if (!std::filesystem::exists(std::filesystem::path(directory) / target_name))
         {
-            bool is_long = false;
-            bool is_coloured = false;
-            std::set<std::string> tracked_dir_set{};
-            print_notstagged(sl, tracked_dir_set, is_long, is_coloured);
+            // Neither a branch/tag nor a file
+            throw git_exception(
+                "error: pathspec '" + target_name + "' did not match any file(s) known to git",
+                git2cpp_error_code::BAD_ARGUMENT
+            );
         }
-        if (sl.has_tobecommited_header())
+
+        options.checkout_strategy = GIT_CHECKOUT_FORCE;
+        checkout_files(repo, file, options);
+        return;
+    }
+
+    auto sl = status_list_wrapper::status_list(repo);
+    try
+    {
+        checkout_tree(repo, *optional_commit, target_name, options);
+        update_head(repo, *optional_commit, target_name);
+    }
+    catch (const git_exception& e)
+    {
+        if (sl.has_notstagged_header())
         {
-            bool is_long = false;
-            bool is_coloured = false;
-            std::set<std::string> tracked_dir_set{};
-            print_tobecommited(sl, tracked_dir_set, is_long, is_coloured);
+            print_no_switch(sl);
         }
-        std::cout << "Switched to branch '" << m_branch_name << "'" << std::endl;
+        throw e;
+    }
+
+    if (sl.has_notstagged_header())
+    {
+        bool is_long = false;
+        bool is_coloured = false;
+        std::set<std::string> tracked_dir_set{};
+        print_notstagged(sl, tracked_dir_set, is_long, is_coloured);
+    }
+    if (sl.has_tobecommited_header())
+    {
+        bool is_long = false;
+        bool is_coloured = false;
+        std::set<std::string> tracked_dir_set{};
+        print_tobecommited(sl, tracked_dir_set, is_long, is_coloured);
+    }
+
+    std::string_view annotated_ref = optional_commit->reference_name();
+    if (!annotated_ref.empty() && repo.find_reference(annotated_ref).is_branch())
+    {
+        std::cout << "Switched to branch '" << target_name << "'" << std::endl;
         print_tracking_info(repo, sl, true, false);
     }
+    else
+    {
+        std::string sha = optional_commit->commit_oid_tostr().substr(0, 7);
+        auto commit = repo.find_commit(optional_commit->oid());
+        std::string summary = commit.summary();
+        std::cout << "HEAD is now at " << sha << " " << summary << std::endl;
+    }
 }
 
 annotated_commit_wrapper
@@ -150,22 +282,71 @@ void checkout_subcommand::update_head(
     const std::string_view target_name
 )
 {
+    // Check if HEAD is already detached or not
+    const bool head_was_detached = [&]()
+    {
+        auto head_ref = repo.head();
+        return !head_ref.is_branch();
+    }();
+
+    // Save previous HEAD info (if it was detached) before changing it (for output message)
+    std::optional<commit_wrapper> previous_head_commit;
+    std::string previous_head_message;
+    if (head_was_detached)
+    {
+        previous_head_commit = repo.find_commit("HEAD");
+        previous_head_message = "Previous HEAD position was "
+                                + std::string(previous_head_commit.value().commit_oid_tostr().substr(0, 7))
+                                + " " + previous_head_commit.value().summary();
+    }
+
     std::string_view annotated_ref = target_annotated_commit.reference_name();
     if (!annotated_ref.empty())
     {
         auto ref = repo.find_reference(annotated_ref);
-        if (ref.is_remote())
+        if (ref.is_branch())
         {
-            auto branch = repo.create_branch(target_name, target_annotated_commit);
-            repo.set_head(branch.reference_name());
+            if (head_was_detached)
+            {
+                std::cout << previous_head_message << std::endl;
+            }
+            repo.set_head(annotated_ref);
+            return;
         }
-        else
+    }
+
+    repo.set_head_detached(target_annotated_commit);
+
+    if (head_was_detached)
+    {
+        // Only print "Previous HEAD position..." if HEAD was already detached before and if there is an
+        // actual checkout
+        auto new_head_commit = repo.find_commit("HEAD");
+        if (!git_oid_equal(&previous_head_commit.value().oid(), &new_head_commit.oid()))
         {
-            repo.set_head(annotated_ref);
+            std::cout << previous_head_message << std::endl;
         }
     }
     else
     {
-        repo.set_head_detached(target_annotated_commit);
+        // Only print the detached-HEAD advice if HEAD was not already detached.
+        std::cout << "Note: switching to '" << target_name << "'." << std::endl;
+        std::cout << std::endl;
+        std::cout << "You are in 'detached HEAD' state. You can look around, make experimental" << std::endl;
+        std::cout << "changes and commit them, and you can discard any commits you make in this" << std::endl;
+        std::cout << "state without impacting any branches by switching back to a branch." << std::endl;
+        std::cout << std::endl;
+
+        // TODO: add to the following when the switch subcommand is implemented:
+        // std::cout << "If you want to create a new branch to retain commits you create, you may" <<
+        // std::endl; std::cout << "do so (now or later) by using -c with the switch command. Example:" <<
+        // std::endl; std::cout << "  git switch -c <new-branch-name>" << std::endl; std::cout << std::endl;
+        // std::cout << "Or undo this operation with:" << std::endl;
+        // std::cout << std::endl;
+        // std::cout << "  git switch -" << std::endl;
+        // std::cout << std::endl;
+        // TODO: add the following later
+        // std::cout << "Turn off this advice by setting config variable advice.detachedHead to false"
+        //             << std::endl;
     }
 }
diff --git a/src/subcommand/checkout_subcommand.hpp b/src/subcommand/checkout_subcommand.hpp
@@ -1,7 +1,7 @@
 #pragma once
 
-#include <optional>
 #include <string>
+#include <vector>
 
 #include <CLI/CLI.hpp>
 
@@ -33,7 +33,20 @@ class checkout_subcommand
         const std::string_view target_name
     );
 
-    std::string m_branch_name = {};
+    void checkout_files(
+        const repository_wrapper& repo,
+        const std::vector<std::string>& files,
+        const git_checkout_options& options
+    );
+
+    void checkout_paths(
+        const repository_wrapper& repo,
+        const std::string_view tree_ish,
+        const std::vector<std::string>& pathspecs,
+        const git_checkout_options& options
+    );
+
+    std::vector<std::string> m_positional_args = {};
     bool m_create_flag = false;
     bool m_force_create_flag = false;
     bool m_force_checkout_flag = false;

diff --git a/src/wrapper/annotated_commit_wrapper.cpp b/src/wrapper/annotated_commit_wrapper.cpp
@@ -16,6 +16,12 @@ const git_oid& annotated_commit_wrapper::oid() const
     return *git_annotated_commit_id(p_resource);
 }
 
+std::string annotated_commit_wrapper::commit_oid_tostr() const
+{
+    char buf[GIT_OID_SHA1_HEXSIZE + 1];
+    return git_oid_tostr(buf, sizeof(buf), &this->oid());
+}
+
 std::string_view annotated_commit_wrapper::reference_name() const
 {
     const char* res = git_annotated_commit_ref(*this);

diff --git a/src/wrapper/annotated_commit_wrapper.hpp b/src/wrapper/annotated_commit_wrapper.hpp
@@ -1,5 +1,6 @@
 #pragma once
 
+#include <string>
 #include <string_view>
 
 #include <git2.h>
@@ -18,6 +19,7 @@ class annotated_commit_wrapper : public wrapper_base<git_annotated_commit>
     annotated_commit_wrapper& operator=(annotated_commit_wrapper&&) noexcept = default;
 
     const git_oid& oid() const;
+    std::string commit_oid_tostr() const;
     std::string_view reference_name() const;
 
 private:

diff --git a/src/wrapper/refs_wrapper.cpp b/src/wrapper/refs_wrapper.cpp
@@ -27,6 +27,11 @@ bool reference_wrapper::is_remote() const
     return git_reference_is_remote(*this);
 }
 
+bool reference_wrapper::is_branch() const
+{
+    return git_reference_is_branch(*this);
+}
+
 const git_oid* reference_wrapper::target() const
 {
     return git_reference_target(p_resource);