use anyhow::{Context, Result};
use axum::extract::FromRef;
use futures::Future;
use lettre::{AsyncSmtpTransport, AsyncTransport, Tokio1Executor};
use serde::{Serialize, Serializer};

use crate::app_state::AppState;

const POSTMARK_EMAIL_BATCH_URL: &str = "https://api.postmarkapp.com/email/batch";

#[derive(Clone, Serialize)]
pub struct Message {
    #[serde(rename = "From")]
    pub from: lettre::message::Mailbox,
    #[serde(rename = "To")]
    #[serde(serialize_with = "serialize_mailboxes")]
    pub to: lettre::message::Mailboxes,
    #[serde(rename = "Subject")]
    pub subject: String,
    #[serde(rename = "TextBody")]
    pub text_body: String,
}

pub trait MailSender: Clone + Sync {
    /// Attempt to send all messages defined by the input Vec. Send as many as
    /// possible, returning exactly one Result<()> for each message.
    fn send_batch(&self, emails: Vec<Message>) -> impl Future<Output = Vec<Result<()>>>;
}

#[derive(Clone, Debug)]
pub enum Mailer {
    Smtp(SmtpSender),
    Postmark(PostmarkSender),
}

impl Mailer {
    pub fn new_smtp(opts: SmtpOptions) -> Result<Self> {
        Ok(Self::Smtp(SmtpSender::new(opts)?))
    }

    pub fn new_postmark(server_token: String) -> Result<Self> {
        Ok(Self::Postmark(PostmarkSender::new(server_token)?))
    }

    pub fn with_reqwest_client(self, client: reqwest::Client) -> Self {
        match self {
            Self::Postmark(sender) => Self::Postmark(sender.with_reqwest_client(client)),
            _ => self,
        }
    }
}

impl MailSender for Mailer {
    async fn send_batch(&self, emails: Vec<Message>) -> Vec<Result<()>> {
        match self {
            Mailer::Smtp(sender) => sender.send_batch(emails).await,
            Mailer::Postmark(sender) => sender.send_batch(emails).await,
        }
    }
}

#[derive(Clone, Debug)]
pub struct SmtpSender {
    transport: AsyncSmtpTransport<Tokio1Executor>,
}

#[derive(Debug)]
pub struct SmtpOptions {
    pub server: String,
    pub username: String,
    pub password: String,
}

impl SmtpSender {
    fn new(opts: SmtpOptions) -> Result<Self> {
        let mailer_creds =
            lettre::transport::smtp::authentication::Credentials::new(opts.username, opts.password);
        let transport = lettre::AsyncSmtpTransport::<Tokio1Executor>::starttls_relay(&opts.server)
            .context("unable to initialize starttls_relay")?
            .credentials(mailer_creds)
            .build();
        Ok(Self { transport })
    }
}

impl TryInto<lettre::Message> for Message {
    type Error = anyhow::Error;

    fn try_into(self) -> Result<lettre::Message, Self::Error> {
        let mut builder = lettre::Message::builder()
            .from(self.from.clone())
            .subject(self.subject)
            .header(lettre::message::header::ContentType::TEXT_PLAIN);
        for to_addr in self.to {
            builder = builder.to(to_addr);
        }
        let message = builder.body(self.text_body)?;
        Ok(message)
    }
}

fn serialize_mailboxes<S>(t: &lettre::message::Mailboxes, s: S) -> Result<S::Ok, S::Error>
where
    S: Serializer,
{
    s.serialize_str(&t.to_string())
}

impl MailSender for SmtpSender {
    async fn send_batch(&self, emails: Vec<Message>) -> Vec<Result<()>> {
        let mut results: Vec<Result<()>> = Vec::with_capacity(emails.len());
        for email in emails {
            match TryInto::<lettre::Message>::try_into(email) {
                Ok(email) => {
                    results.push(
                        self.transport
                            .send(email)
                            .await
                            .map(|_| ())
                            .map_err(Into::<anyhow::Error>::into),
                    );
                }
                Err(err) => {
                    results.push(Err(err));
                }
            }
        }
        results
    }
}

#[derive(Clone, Debug)]
pub struct PostmarkSender {
    client: reqwest::Client,
    server_token: String,
}

impl PostmarkSender {
    fn new(server_token: String) -> Result<Self> {
        Ok(Self {
            client: reqwest::ClientBuilder::new().https_only(true).build()?,
            server_token,
        })
    }

    pub fn with_reqwest_client(self, client: reqwest::Client) -> Self {
        Self { client, ..self }
    }
}

impl MailSender for PostmarkSender {
    /// Recursively attempts to send messages, breaking them into smaller and
    /// smaller batches as needed.
    async fn send_batch(&self, mut emails: Vec<Message>) -> Vec<Result<()>> {
        /// Constructs a Vec with Ok(()) repeated n times.
        macro_rules! all_ok {
            () => {{
                let mut collection: Vec<Result<_>> = Vec::with_capacity(emails.len());
                for _ in 0..emails.len() {
                    collection.push(Ok(()));
                }
                collection
            }};
        }

        /// Constructs a Vec with a single specific error, followed by n-1
        /// generic errors referring back to it.
        macro_rules! cascade_err {
            ($err:expr) => {{
                let mut collection: Vec<Result<_>> = Vec::with_capacity(emails.len());
                collection.push(Err($err));
                for _ in 1..emails.len() {
                    collection.push(Err(anyhow::anyhow!("could not send due to previous error")));
                }
                collection
            }};
        }

        /// Recursively splits the email batch in half and tries to send each
        /// half independently, allowing both to run to completion and then
        /// returning the first error of the two results, if present.
        macro_rules! split_and_retry {
            // This is implemented as a macro in order to avoid unstable async
            // closures.
            () => {
                if emails.len() < 2 {
                    tracing::warn!("Postmark send batch cannot be split any further");
                    vec![Err(anyhow::anyhow!(
                        "unable to split Postmark batch into smaller slices"
                    ))]
                } else {
                    tracing::debug!("retrying Postmark send with smaller batches");
                    let mut results =
                        Box::pin(self.send_batch(emails.split_off(emails.len() / 2))).await;
                    results.extend(Box::pin(self.send_batch(emails)).await);
                    results
                }
            };
        }

        // https://postmarkapp.com/support/article/1056-what-are-the-attachment-and-email-size-limits
        const POSTMARK_MAX_BATCH_ENTRIES: usize = 500;
        const POSTMARK_MAX_REQUEST_BYTES: usize = 50 * 1000 * 1000;
        // TODO: Check email subject and body size against Postmark limits

        if emails.is_empty() {
            tracing::debug!("no Postmark messages to send");
            vec![Ok(())]
        } else if emails.len() > POSTMARK_MAX_BATCH_ENTRIES {
            split_and_retry!()
        } else {
            let body = match serde_json::to_string(&emails) {
                Ok(body) => body,
                Err(err) => return cascade_err!(err.into()),
            };
            if body.len() > POSTMARK_MAX_REQUEST_BYTES {
                if emails.len() > 1 {
                    split_and_retry!()
                } else {
                    vec![Err(anyhow::anyhow!(
                        "Postmark requests may not exceed {} bytes",
                        POSTMARK_MAX_REQUEST_BYTES
                    ))]
                }
            } else {
                tracing::debug!("sending Postmark batch of {} messages", emails.len());
                let resp = match self
                    .client
                    .post(POSTMARK_EMAIL_BATCH_URL)
                    .header("X-Postmark-Server-Token", &self.server_token)
                    .header(reqwest::header::CONTENT_TYPE, "application/json")
                    .body(body)
                    .send()
                    .await
                {
                    Ok(resp) => resp,
                    Err(err) => return cascade_err!(err.into()),
                };
                if resp.status().is_client_error() && emails.len() > 1 {
                    split_and_retry!()
                } else if let Err(err) = resp.error_for_status() {
                    cascade_err!(err.into())
                } else {
                    tracing::debug!("sent Postmark batch of {} messages", emails.len());
                    all_ok!()
                }
            }
        }
    }
}

impl FromRef<AppState> for Mailer {
    fn from_ref(state: &AppState) -> Mailer {
        state.mailer.clone()
    }
}