diff --git a/crates/radicle-cli/examples/rad-init-detached-head.md b/crates/radicle-cli/examples/rad-init-detached-head.md
new file mode 100644
index 00000000..8935abd0
--- /dev/null
+++ b/crates/radicle-cli/examples/rad-init-detached-head.md
@@ -0,0 +1,29 @@
+Let's assume you created a Git repository containing two commits and checked out
+the first one, leaving you in a detached `HEAD` state:
+
+```
+$ git init -q
+$ touch file1.txt
+$ git add .
+$ git commit -m "Create file" -q
+$ touch file2.txt
+$ git add .
+$ git commit -m "Create a second file" -q
+$ git checkout HEAD~1
+```
+
+If you try to `rad init` the repository in this state, it will attempt to
+determine a default branch. However, it cannot because we are currently not on
+any branch nor have we set the `init.defaultBranch` option in our `git config`.
+
+Using `rad init` will fail, providing a hint on how to fix the issue:
+
+``` (fail)
+$ rad init
+✗ Error: in detached HEAD state
+✗ Hint: try `git checkout <default branch>` or set `git config set --local init.defaultBranch <default branch>`
+✗ Error: aborting `rad init`
+```
+
+Alternatively, if you know a branch that already exists, and you would like to
+use, you can use the `--default-branch` option.
diff --git a/crates/radicle-cli/examples/rad-init-no-git.md b/crates/radicle-cli/examples/rad-init-no-git.md
index 505c426a..b39e914d 100644
--- a/crates/radicle-cli/examples/rad-init-no-git.md
+++ b/crates/radicle-cli/examples/rad-init-no-git.md
@@ -16,7 +16,10 @@ Now we try again.
 
 ``` (fail)
 $ rad init
-✗ Error: repository head must point to a commit
+✗ Error: could not determine default branch in repository
+✗ Hint: perhaps you need to create a branch?
+✗ Error: aborting `rad init`
 ```
 
-Looks like we need a commit.
+Looks like we need to get to work and start working on a branch and add commits
+to it.
diff --git a/crates/radicle-cli/src/commands/init.rs b/crates/radicle-cli/src/commands/init.rs
index b837f558..76822e0b 100644
--- a/crates/radicle-cli/src/commands/init.rs
+++ b/crates/radicle-cli/src/commands/init.rs
@@ -12,6 +12,7 @@ use serde_json as json;
 
 use radicle::crypto::ssh;
 use radicle::explorer::ExplorerUrl;
+use radicle::git::raw;
 use radicle::git::RefString;
 use radicle::identity::project::ProjectName;
 use radicle::identity::{Doc, RepoId, Visibility};
@@ -216,11 +217,21 @@ pub fn init(
         .unwrap_or_else(|| repo.path())
         .canonicalize()?;
     let interactive = options.interactive;
-    let head: String = repo
-        .head()
-        .ok()
-        .and_then(|head| head.shorthand().map(|h| h.to_owned()))
-        .ok_or_else(|| anyhow!("repository head must point to a commit"))?;
+
+    let default_branch = match find_default_branch(&repo) {
+        Err(err @ DefaultBranchError::Head) => {
+            term::error(err);
+            term::hint("try `git checkout <default branch>` or set `git config set --local init.defaultBranch <default branch>`");
+            anyhow::bail!("aborting `rad init`")
+        }
+        Err(err @ DefaultBranchError::NoHead) => {
+            term::error(err);
+            term::hint("perhaps you need to create a branch?");
+            anyhow::bail!("aborting `rad init`")
+        }
+        Err(err) => anyhow::bail!(err),
+        Ok(branch) => branch,
+    };
 
     term::headline(format!(
         "Initializing{}radicle 👾 repository in {}..",
@@ -252,10 +263,10 @@ pub fn init(
         Some(branch) => branch,
         None if interactive.yes() => term::input(
             "Default branch",
-            Some(head),
+            Some(default_branch),
             Some("Please specify an existing branch"),
         )?,
-        None => head,
+        None => default_branch,
     };
     let branch = RefString::try_from(branch.clone())
         .map_err(|e| anyhow!("invalid branch name {:?}: {}", branch, e))?;
@@ -671,3 +682,39 @@ pub fn setup_signing(
     }
     Ok(())
 }
+
+#[derive(Debug, thiserror::Error)]
+enum DefaultBranchError {
+    #[error("could not determine default branch in repository")]
+    NoHead,
+    #[error("in detached HEAD state")]
+    Head,
+    #[error("could not determine default branch in repository: {0}")]
+    Git(raw::Error),
+}
+
+fn find_default_branch(repo: &raw::Repository) -> Result<String, DefaultBranchError> {
+    match find_init_default_branch(repo).ok().flatten() {
+        Some(refname) => Ok(refname),
+        None => Ok(find_repository_head(repo)?),
+    }
+}
+
+fn find_init_default_branch(repo: &raw::Repository) -> Result<Option<String>, raw::Error> {
+    let config = repo.config().and_then(|mut c| c.snapshot())?;
+    let default_branch = config.get_str("init.defaultbranch")?;
+    let branch = repo.find_branch(default_branch, raw::BranchType::Local)?;
+    Ok(branch.into_reference().shorthand().map(ToOwned::to_owned))
+}
+
+fn find_repository_head(repo: &raw::Repository) -> Result<String, DefaultBranchError> {
+    match repo.head() {
+        Err(e) if e.code() == raw::ErrorCode::UnbornBranch => Err(DefaultBranchError::NoHead),
+        Err(e) => Err(DefaultBranchError::Git(e)),
+        Ok(head) => head
+            .shorthand()
+            .filter(|refname| *refname != "HEAD")
+            .ok_or(DefaultBranchError::Head)
+            .map(|refname| refname.to_owned()),
+    }
+}
diff --git a/crates/radicle-cli/tests/commands.rs b/crates/radicle-cli/tests/commands.rs
index 51699600..9ef56f75 100644
--- a/crates/radicle-cli/tests/commands.rs
+++ b/crates/radicle-cli/tests/commands.rs
@@ -212,6 +212,18 @@ fn rad_init_no_git() {
     environment.test("rad-init-no-git", &profile).unwrap();
 }
 
+#[test]
+fn rad_init_detached_head() {
+    let mut environment = Environment::new();
+    let profile = environment.profile("alice");
+
+    // NOTE: There is no repository set up here.
+
+    environment
+        .test("rad-init-detached-head", &profile)
+        .unwrap();
+}
+
 #[test]
 fn rad_inspect() {
     let mut environment = Environment::new();
diff --git a/crates/radicle/src/git.rs b/crates/radicle/src/git.rs
index 7a67f4fa..e7d13117 100644
--- a/crates/radicle/src/git.rs
+++ b/crates/radicle/src/git.rs
@@ -701,6 +701,22 @@ pub fn set_upstream(
     Ok(())
 }
 
+pub fn init_default_branch(repo: &git2::Repository) -> Result<Option<String>, git2::Error> {
+    let config = repo.config().and_then(|mut c| c.snapshot())?;
+    let default_branch = config.get_str("init.defaultbranch")?;
+    let branch = repo.find_branch(default_branch, git2::BranchType::Local)?;
+    Ok(branch.into_reference().shorthand().map(ToOwned::to_owned))
+}
+
+pub fn head_refname(repo: &git2::Repository) -> Result<Option<String>, git2::Error> {
+    let head = repo.head()?;
+    match head.shorthand() {
+        Some("HEAD") => Ok(None),
+        Some(refname) => Ok(Some(refname.to_owned())),
+        None => Ok(None),
+    }
+}
+
 /// Execute a git command by spawning a child process.
 pub fn run<P, S, K, V>(
     repo: P,