smtp: send messages with a PDF attachment

2 files changed, 975 insertions, 0 deletions

diff --git a/src/smtp.c b/src/smtp.c
new file mode 100644
index 0000000..ed70519
--- /dev/null
+++ b/src/smtp.c
@@ -0,0 +1,951 @@
+#include "smtp.h"
+
+#include <ctype.h>
+#include <errno.h>
+#include <limits.h>
+#include <netdb.h>
+#include <stdarg.h>
+#include <stdio.h>
+#include <stdlib.h>
+#include <string.h>
+#include <strings.h>
+#include <sys/socket.h>
+#include <sys/time.h>
+#include <time.h>
+#include <unistd.h>
+
+#include <openssl/err.h>
+#include <openssl/ssl.h>
+#include <openssl/x509.h>
+
+#include "util.h"
+
+#define SMTP_TIMEOUT_SEC 30
+#define SMTP_LINE_MAX 1024
+#define SMTP_REPLY_TEXT_MAX 2048
+#define SMTP_READ_BUF 4096
+
+struct smtp_conn {
+    int fd;
+    SSL_CTX *ctx;
+    SSL *ssl;
+    unsigned char in[SMTP_READ_BUF];
+    size_t in_len;
+    size_t in_pos;
+};
+
+struct smtp_reply {
+    int code;
+    char text[SMTP_REPLY_TEXT_MAX];
+};
+
+static void set_err(char *err, size_t errlen, const char *fmt, ...)
+{
+    if (!err || errlen == 0)
+        return;
+    va_list ap;
+    va_start(ap, fmt);
+    vsnprintf(err, errlen, fmt, ap);
+    va_end(ap);
+}
+
+static void buf_append_str(struct buf *b, const char *s)
+{
+    buf_append(b, s, strlen(s));
+}
+
+static void buf_appendf(struct buf *b, const char *fmt, ...)
+{
+    va_list ap;
+    va_start(ap, fmt);
+    char tmp[512];
+    int n = vsnprintf(tmp, sizeof tmp, fmt, ap);
+    va_end(ap);
+    if (n < 0)
+        return;
+    if ((size_t)n < sizeof tmp) {
+        buf_append(b, tmp, (size_t)n);
+        return;
+    }
+    char *big = xmalloc((size_t)n + 1);
+    va_start(ap, fmt);
+    vsnprintf(big, (size_t)n + 1, fmt, ap);
+    va_end(ap);
+    buf_append(b, big, (size_t)n);
+    free(big);
+}
+
+static void conn_close(struct smtp_conn *c)
+{
+    if (c->ssl) {
+        SSL_shutdown(c->ssl);
+        SSL_free(c->ssl);
+        c->ssl = NULL;
+    }
+    if (c->ctx) {
+        SSL_CTX_free(c->ctx);
+        c->ctx = NULL;
+    }
+    if (c->fd >= 0) {
+        close(c->fd);
+        c->fd = -1;
+    }
+}
+
+static int conn_write(struct smtp_conn *c, const void *data, size_t n,
+                      char *err, size_t errlen)
+{
+    const unsigned char *p = data;
+    while (n > 0) {
+        ssize_t w;
+        if (c->ssl) {
+            int chunk = n > (size_t)INT_MAX ? INT_MAX : (int)n;
+            w = SSL_write(c->ssl, p, chunk);
+            if (w <= 0) {
+                int e = SSL_get_error(c->ssl, (int)w);
+                if (e == SSL_ERROR_WANT_READ || e == SSL_ERROR_WANT_WRITE)
+                    continue;
+                set_err(err, errlen, "smtp: TLS write failed");
+                return -1;
+            }
+        } else {
+            w = send(c->fd, p, n, MSG_NOSIGNAL);
+            if (w < 0) {
+                if (errno == EINTR)
+                    continue;
+                if (errno == EAGAIN || errno == EWOULDBLOCK) {
+                    set_err(err, errlen, "smtp: send timed out");
+                    return -1;
+                }
+                set_err(err, errlen, "smtp: send failed: %s",
+                        strerror(errno));
+                return -1;
+            }
+        }
+        p += (size_t)w;
+        n -= (size_t)w;
+    }
+    return 0;
+}
+
+static int conn_line(struct smtp_conn *c, const char *line, char *err,
+                     size_t errlen)
+{
+    if (conn_write(c, line, strlen(line), err, errlen) != 0)
+        return -1;
+    return conn_write(c, "\r\n", 2, err, errlen);
+}
+
+static int conn_buf_line(struct smtp_conn *c, const struct buf *b, char *err,
+                         size_t errlen)
+{
+    if (conn_write(c, b->p, b->len, err, errlen) != 0)
+        return -1;
+    return conn_write(c, "\r\n", 2, err, errlen);
+}
+
+static int conn_fill(struct smtp_conn *c, char *err, size_t errlen)
+{
+    for (;;) {
+        if (c->ssl) {
+            int n = SSL_read(c->ssl, c->in, (int)sizeof c->in);
+            if (n > 0) {
+                c->in_len = (size_t)n;
+                c->in_pos = 0;
+                return 0;
+            }
+            int e = SSL_get_error(c->ssl, n);
+            if (e == SSL_ERROR_WANT_READ || e == SSL_ERROR_WANT_WRITE)
+                continue;
+            if (e == SSL_ERROR_ZERO_RETURN) {
+                set_err(err, errlen, "smtp: connection closed by server");
+                return -1;
+            }
+            if (e == SSL_ERROR_SYSCALL && n == 0) {
+                set_err(err, errlen, "smtp: connection closed by server");
+                return -1;
+            }
+            if (e == SSL_ERROR_SYSCALL &&
+                (errno == EAGAIN || errno == EWOULDBLOCK)) {
+                set_err(err, errlen, "smtp: receive timed out");
+                return -1;
+            }
+            unsigned long ec = ERR_get_error();
+            if (ec)
+                set_err(err, errlen, "smtp: TLS read failed: %s",
+                        ERR_error_string(ec, NULL));
+            else
+                set_err(err, errlen, "smtp: TLS read failed");
+            return -1;
+        }
+        ssize_t n = recv(c->fd, c->in, sizeof c->in, 0);
+        if (n > 0) {
+            c->in_len = (size_t)n;
+            c->in_pos = 0;
+            return 0;
+        }
+        if (n == 0) {
+            set_err(err, errlen, "smtp: connection closed by server");
+            return -1;
+        }
+        if (errno == EINTR)
+            continue;
+        if (errno == EAGAIN || errno == EWOULDBLOCK) {
+            set_err(err, errlen, "smtp: receive timed out");
+            return -1;
+        }
+        set_err(err, errlen, "smtp: receive failed: %s", strerror(errno));
+        return -1;
+    }
+}
+
+static int conn_read_line(struct smtp_conn *c, char *out, size_t outsz,
+                          char *err, size_t errlen)
+{
+    size_t o = 0;
+    for (;;) {
+        if (c->in_pos >= c->in_len) {
+            if (conn_fill(c, err, errlen) != 0)
+                return -1;
+        }
+        unsigned char ch = c->in[c->in_pos++];
+        if (ch == '\n') {
+            while (o > 0 && out[o - 1] == '\r')
+                o--;
+            out[o] = '\0';
+            return 0;
+        }
+        if (o + 1 < outsz)
+            out[o++] = (char)ch;
+    }
+}
+
+static int parse_code(const char *line, int *code)
+{
+    if (strlen(line) < 3)
+        return -1;
+    for (int i = 0; i < 3; i++)
+        if (!isdigit((unsigned char)line[i]))
+            return -1;
+    *code = (line[0] - '0') * 100 + (line[1] - '0') * 10 + (line[2] - '0');
+    return 0;
+}
+
+static int conn_read_reply(struct smtp_conn *c, struct smtp_reply *r,
+                           char *err, size_t errlen)
+{
+    char line[SMTP_LINE_MAX];
+    size_t tlen = 0;
+    r->code = 0;
+    r->text[0] = '\0';
+    for (;;) {
+        if (conn_read_line(c, line, sizeof line, err, errlen) != 0)
+            return -1;
+        int code;
+        if (parse_code(line, &code) != 0) {
+            set_err(err, errlen, "smtp: malformed server reply");
+            return -1;
+        }
+        r->code = code;
+        const char *text = line + 3;
+        while (*text == ' ' || *text == '-')
+            text++;
+        if (*text) {
+            size_t n = strlen(text);
+            if (tlen) {
+                if (tlen + 1 < sizeof r->text)
+                    r->text[tlen++] = '\n';
+                else
+                    n = 0;
+            }
+            if (tlen + n >= sizeof r->text)
+                n = sizeof r->text - 1 - tlen;
+            memcpy(r->text + tlen, text, n);
+            tlen += n;
+            r->text[tlen] = '\0';
+        }
+        if (line[3] != '-')
+            break;
+    }
+    return 0;
+}
+
+static int conn_expect(struct smtp_conn *c, int want, const char *what,
+                       char *err, size_t errlen)
+{
+    struct smtp_reply r;
+    if (conn_read_reply(c, &r, err, errlen) != 0)
+        return -1;
+    if (r.code != want) {
+        if (r.text[0])
+            set_err(err, errlen, "%s: server said %d %s", what, r.code,
+                    r.text);
+        else
+            set_err(err, errlen, "%s: server said %d", what, r.code);
+        return -1;
+    }
+    return 0;
+}
+
+static int tcp_connect(struct smtp_conn *c, const char *host, int port,
+                       char *err, size_t errlen)
+{
+    char portstr[16];
+    snprintf(portstr, sizeof portstr, "%d", port);
+    struct addrinfo hints;
+    memset(&hints, 0, sizeof hints);
+    hints.ai_family = AF_UNSPEC;
+    hints.ai_socktype = SOCK_STREAM;
+    struct addrinfo *res = NULL;
+    int gai = getaddrinfo(host, portstr, &hints, &res);
+    if (gai != 0) {
+        set_err(err, errlen, "smtp: cannot resolve %s: %s", host,
+                gai_strerror(gai));
+        return -1;
+    }
+    int last = 0;
+    for (struct addrinfo *ai = res; ai; ai = ai->ai_next) {
+        int fd = socket(ai->ai_family, ai->ai_socktype | SOCK_CLOEXEC,
+                        ai->ai_protocol);
+        if (fd < 0) {
+            last = errno;
+            continue;
+        }
+        struct timeval tv;
+        tv.tv_sec = SMTP_TIMEOUT_SEC;
+        tv.tv_usec = 0;
+        (void)setsockopt(fd, SOL_SOCKET, SO_RCVTIMEO, &tv, sizeof tv);
+        (void)setsockopt(fd, SOL_SOCKET, SO_SNDTIMEO, &tv, sizeof tv);
+        if (connect(fd, ai->ai_addr, ai->ai_addrlen) == 0) {
+            c->fd = fd;
+            freeaddrinfo(res);
+            return 0;
+        }
+        last = errno;
+        close(fd);
+    }
+    freeaddrinfo(res);
+    if (last)
+        set_err(err, errlen, "smtp: cannot connect to %s:%d: %s", host, port,
+                strerror(last));
+    else
+        set_err(err, errlen, "smtp: cannot connect to %s:%d", host, port);
+    return -1;
+}
+
+static int tls_start(struct smtp_conn *c, const char *host, char *err,
+                     size_t errlen)
+{
+    c->ctx = SSL_CTX_new(TLS_client_method());
+    if (!c->ctx) {
+        set_err(err, errlen, "smtp: cannot create TLS context");
+        return -1;
+    }
+    SSL_CTX_set_min_proto_version(c->ctx, TLS1_2_VERSION);
+    SSL_CTX_set_options(c->ctx, SSL_OP_NO_COMPRESSION |
+                                    SSL_OP_NO_RENEGOTIATION);
+    SSL_CTX_set_verify(c->ctx, SSL_VERIFY_PEER, NULL);
+    if (SSL_CTX_set_default_verify_paths(c->ctx) != 1) {
+        set_err(err, errlen, "smtp: cannot load system CA certificates");
+        return -1;
+    }
+    c->ssl = SSL_new(c->ctx);
+    if (!c->ssl) {
+        set_err(err, errlen, "smtp: cannot create TLS connection");
+        return -1;
+    }
+    if (SSL_set_fd(c->ssl, c->fd) != 1 ||
+        SSL_set_tlsext_host_name(c->ssl, host) != 1 ||
+        SSL_set1_host(c->ssl, host) != 1) {
+        set_err(err, errlen, "smtp: cannot set up TLS connection");
+        return -1;
+    }
+    if (SSL_connect(c->ssl) != 1) {
+        long vr = SSL_get_verify_result(c->ssl);
+        unsigned long ec = ERR_get_error();
+        if (vr != X509_V_OK)
+            set_err(err, errlen,
+                    "smtp: TLS certificate verification failed: %s",
+                    X509_verify_cert_error_string(vr));
+        else if (ec)
+            set_err(err, errlen, "smtp: TLS handshake failed: %s",
+                    ERR_error_string(ec, NULL));
+        else
+            set_err(err, errlen, "smtp: TLS handshake failed");
+        return -1;
+    }
+    if (SSL_get_verify_result(c->ssl) != X509_V_OK) {
+        set_err(err, errlen, "smtp: TLS certificate verification failed: %s",
+                X509_verify_cert_error_string(SSL_get_verify_result(c->ssl)));
+        return -1;
+    }
+    return 0;
+}
+
+static int mech_offered(const char *caps, const char *mech)
+{
+    if (!caps)
+        return 0;
+    size_t mlen = strlen(mech);
+    for (const char *p = caps; *p;) {
+        const char *line_end = strchr(p, '\n');
+        size_t llen = line_end ? (size_t)(line_end - p) : strlen(p);
+        if (llen >= 4 && strncasecmp(p, "AUTH", 4) == 0) {
+            const char *q = p + 4;
+            const char *end = p + llen;
+            while (q < end) {
+                while (q < end && (*q == ' ' || *q == '=' || *q == '\t'))
+                    q++;
+                const char *w = q;
+                while (q < end && *q != ' ' && *q != '=' && *q != '\t')
+                    q++;
+                size_t wl = (size_t)(q - w);
+                if (wl == mlen && strncasecmp(w, mech, mlen) == 0)
+                    return 1;
+            }
+        }
+        if (!line_end)
+            break;
+        p = line_end + 1;
+    }
+    return 0;
+}
+
+static void ehlo_name(char *out, size_t n)
+{
+    if (gethostname(out, n) != 0 || out[0] == '\0' || !strchr(out, '.'))
+        snprintf(out, n, "localhost");
+    out[n - 1] = '\0';
+}
+
+static int smtp_ehlo(struct smtp_conn *c, const char *name, struct buf *caps,
+                     char *err, size_t errlen)
+{
+    struct buf cmd;
+    buf_init(&cmd);
+    buf_appendf(&cmd, "EHLO %s", name);
+    int rc = conn_buf_line(c, &cmd, err, errlen);
+    buf_free(&cmd);
+    if (rc != 0)
+        return -1;
+    struct smtp_reply r;
+    if (conn_read_reply(c, &r, err, errlen) != 0)
+        return -1;
+    if (r.code != 250) {
+        if (r.text[0])
+            set_err(err, errlen, "EHLO: server said %d %s", r.code, r.text);
+        else
+            set_err(err, errlen, "EHLO: server said %d", r.code);
+        return -1;
+    }
+    caps->len = 0;
+    buf_append(caps, r.text, strlen(r.text) + 1);
+    return 0;
+}
+
+static int auth_plain(struct smtp_conn *c, const char *user, const char *pass,
+                      char *err, size_t errlen)
+{
+    size_t ulen = strlen(user);
+    size_t plen = strlen(pass);
+    unsigned char *raw = xmalloc(ulen + plen + 2);
+    raw[0] = 0;
+    memcpy(raw + 1, user, ulen);
+    raw[1 + ulen] = 0;
+    memcpy(raw + 2 + ulen, pass, plen);
+    char *b64 = util_b64(raw, ulen + plen + 2);
+    free(raw);
+
+    struct buf cmd;
+    buf_init(&cmd);
+    buf_appendf(&cmd, "AUTH PLAIN %s", b64);
+    int rc = conn_buf_line(c, &cmd, err, errlen);
+    buf_free(&cmd);
+    if (rc != 0) {
+        free(b64);
+        return -1;
+    }
+    struct smtp_reply r;
+    if (conn_read_reply(c, &r, err, errlen) != 0) {
+        free(b64);
+        return -1;
+    }
+    if (r.code == 334) {
+        rc = conn_line(c, b64, err, errlen);
+        if (rc == 0 && conn_read_reply(c, &r, err, errlen) != 0)
+            rc = -1;
+    }
+    free(b64);
+    if (rc != 0)
+        return -1;
+    if (r.code != 235) {
+        if (r.text[0])
+            set_err(err, errlen, "AUTH PLAIN rejected: %d %s", r.code,
+                    r.text);
+        else
+            set_err(err, errlen, "AUTH PLAIN rejected: %d", r.code);
+        return -1;
+    }
+    return 0;
+}
+
+static int auth_login(struct smtp_conn *c, const char *user, const char *pass,
+                      char *err, size_t errlen)
+{
+    struct smtp_reply r;
+    if (conn_line(c, "AUTH LOGIN", err, errlen) != 0)
+        return -1;
+    if (conn_read_reply(c, &r, err, errlen) != 0)
+        return -1;
+    if (r.code != 334) {
+        set_err(err, errlen, "AUTH LOGIN rejected: %d", r.code);
+        return -1;
+    }
+    char *ub = util_b64((const unsigned char *)user, strlen(user));
+    int rc = conn_line(c, ub, err, errlen);
+    free(ub);
+    if (rc != 0)
+        return -1;
+    if (conn_read_reply(c, &r, err, errlen) != 0)
+        return -1;
+    if (r.code != 334) {
+        set_err(err, errlen, "AUTH LOGIN rejected: %d", r.code);
+        return -1;
+    }
+    char *pb = util_b64((const unsigned char *)pass, strlen(pass));
+    rc = conn_line(c, pb, err, errlen);
+    free(pb);
+    if (rc != 0)
+        return -1;
+    if (conn_read_reply(c, &r, err, errlen) != 0)
+        return -1;
+    if (r.code != 235) {
+        if (r.text[0])
+            set_err(err, errlen, "AUTH LOGIN rejected: %d %s", r.code,
+                    r.text);
+        else
+            set_err(err, errlen, "AUTH LOGIN rejected: %d", r.code);
+        return -1;
+    }
+    return 0;
+}
+
+static int smtp_auth(struct smtp_conn *c, const struct smtp_message *m,
+                     const char *caps, char *err, size_t errlen)
+{
+    if (!m->user || !m->user[0])
+        return 0;
+    const char *pass = m->password ? m->password : "";
+    if (mech_offered(caps, "PLAIN"))
+        return auth_plain(c, m->user, pass, err, errlen);
+    if (mech_offered(caps, "LOGIN"))
+        return auth_login(c, m->user, pass, err, errlen);
+    set_err(err, errlen, "smtp: server offers no supported AUTH mechanism");
+    return -1;
+}
+
+static int normalize_addr(const char *in, char *out, size_t outsz)
+{
+    while (*in == ' ' || *in == '\t')
+        in++;
+    size_t n = strlen(in);
+    while (n > 0 && (in[n - 1] == ' ' || in[n - 1] == '\t'))
+        n--;
+    if (n >= 2 && in[0] == '<' && in[n - 1] == '>') {
+        in++;
+        n -= 2;
+    }
+    if (n == 0 || n >= outsz)
+        return -1;
+    for (size_t i = 0; i < n; i++) {
+        unsigned char ch = (unsigned char)in[i];
+        if (ch <= 0x20 || ch == 0x7f || ch == '<' || ch == '>')
+            return -1;
+    }
+    memcpy(out, in, n);
+    out[n] = '\0';
+    return 0;
+}
+
+static int ascii_printable(const char *s)
+{
+    for (; *s; s++) {
+        unsigned char ch = (unsigned char)*s;
+        if (ch < 0x20 || ch >= 0x7f)
+            return 0;
+    }
+    return 1;
+}
+
+static int needs_quoting(const char *s)
+{
+    if (!*s)
+        return 1;
+    size_t n = strlen(s);
+    if (*s == ' ' || *s == '\t' || s[n - 1] == ' ' || s[n - 1] == '\t')
+        return 1;
+    for (const char *p = s; *p; p++)
+        if (strchr("()<>[]:;@\\,.\"", *p))
+            return 1;
+    return 0;
+}
+
+static size_t last_line_len(const struct buf *b)
+{
+    size_t i = b->len;
+    while (i > 0 && b->p[i - 1] != '\n')
+        i--;
+    return b->len - i;
+}
+
+static void append_encoded_words(struct buf *b, const char *s)
+{
+    size_t i = 0;
+    while (s[i]) {
+        size_t start = i;
+        size_t chunk = 0;
+        while (s[i] && chunk < 45) {
+            unsigned char ch = (unsigned char)s[i];
+            size_t clen;
+            if (ch < 0x80)
+                clen = 1;
+            else if ((ch & 0xE0) == 0xC0)
+                clen = 2;
+            else if ((ch & 0xF0) == 0xE0)
+                clen = 3;
+            else if ((ch & 0xF8) == 0xF0)
+                clen = 4;
+            else
+                clen = 1;
+            if (chunk + clen > 45)
+                break;
+            chunk += clen;
+            i += clen;
+        }
+        if (chunk == 0) {
+            chunk = 1;
+            i++;
+        }
+        char *b64 = util_b64((const unsigned char *)(s + start), chunk);
+        if (start > 0) {
+            if (last_line_len(b) > 60)
+                buf_append_str(b, "\r\n ");
+            else
+                buf_append_str(b, " ");
+        }
+        buf_append(b, "=?UTF-8?B?", 10);
+        buf_append(b, b64, strlen(b64));
+        buf_append(b, "?=", 2);
+        free(b64);
+    }
+}
+
+static char *sanitize_dup(const char *s)
+{
+    size_t n = strlen(s);
+    char *out = xmalloc(n + 1);
+    for (size_t i = 0; i < n; i++) {
+        unsigned char ch = (unsigned char)s[i];
+        out[i] = (ch == '\r' || ch == '\n') ? ' ' : (char)ch;
+    }
+    out[n] = '\0';
+    return out;
+}
+
+static void append_phrase(struct buf *b, const char *s)
+{
+    if (ascii_printable(s) && !needs_quoting(s)) {
+        buf_append(b, s, strlen(s));
+        return;
+    }
+    if (ascii_printable(s)) {
+        buf_append(b, "\"", 1);
+        for (const char *p = s; *p; p++) {
+            if (*p == '"' || *p == '\\')
+                buf_append(b, "\\", 1);
+            buf_append(b, p, 1);
+        }
+        buf_append(b, "\"", 1);
+        return;
+    }
+    append_encoded_words(b, s);
+}
+
+static void append_b64_wrapped(struct buf *out, const unsigned char *data,
+                               size_t n)
+{
+    if (n == 0)
+        return;
+    char *b64 = util_b64(data, n);
+    size_t len = strlen(b64);
+    for (size_t i = 0; i < len; i += 76) {
+        size_t chunk = len - i < 76 ? len - i : 76;
+        buf_append(out, b64 + i, chunk);
+        buf_append(out, "\r\n", 2);
+    }
+    free(b64);
+}
+
+static void append_quoted_param(struct buf *b, const char *s)
+{
+    for (; *s; s++) {
+        if (*s == '"' || *s == '\\')
+            buf_append(b, "\\", 1);
+        buf_append(b, s, 1);
+    }
+}
+
+static void copy_str(char *dst, size_t n, const char *src)
+{
+    size_t len = strlen(src);
+    if (len >= n)
+        len = n - 1;
+    memcpy(dst, src, len);
+    dst[len] = '\0';
+}
+
+static void message_domain(const char *from, char *out, size_t outsz)
+{
+    const char *at = strrchr(from, '@');
+    if (at && at[1])
+        copy_str(out, outsz, at + 1);
+    else
+        copy_str(out, outsz, "localhost");
+    for (char *p = out; *p; p++) {
+        unsigned char ch = (unsigned char)*p;
+        if (ch < 0x21 || ch > 0x7e || ch == '<' || ch == '>' || ch == '[' ||
+            ch == ']' || ch == '\\')
+            *p = '_';
+    }
+}
+
+static int build_message(const struct smtp_message *m, const char *from,
+                         const char *to, struct buf *out, char *err,
+                         size_t errlen)
+{
+    unsigned char rnd[12];
+    if (util_random(rnd, sizeof rnd) != 0) {
+        set_err(err, errlen, "smtp: no entropy source");
+        return -1;
+    }
+    char rhex[25];
+    util_hex(rnd, sizeof rnd, rhex);
+
+    char domain[256];
+    message_domain(from, domain, sizeof domain);
+
+    char date[64];
+    time_t now = time(NULL);
+    struct tm tm;
+    if (gmtime_r(&now, &tm))
+        strftime(date, sizeof date, "%a, %d %b %Y %H:%M:%S +0000", &tm);
+    else
+        snprintf(date, sizeof date, "Thu, 01 Jan 1970 00:00:00 +0000");
+
+    buf_append_str(out, "From: ");
+    if (m->from_name && m->from_name[0]) {
+        char *name = sanitize_dup(m->from_name);
+        append_phrase(out, name);
+        free(name);
+        buf_append_str(out, " ");
+    }
+    buf_appendf(out, "<%s>\r\n", from);
+    buf_appendf(out, "To: <%s>\r\n", to);
+
+    char *subject = sanitize_dup(m->subject ? m->subject : "");
+    buf_append_str(out, "Subject: ");
+    if (ascii_printable(subject))
+        buf_append(out, subject, strlen(subject));
+    else
+        append_encoded_words(out, subject);
+    free(subject);
+    buf_append_str(out, "\r\n");
+
+    buf_appendf(out, "Date: %s\r\n", date);
+    buf_appendf(out, "Message-ID: <%s.%ld@%s>\r\n", rhex, (long)getpid(),
+                domain);
+    buf_append_str(out, "MIME-Version: 1.0\r\n");
+
+    int has_attach = m->attach_name && m->attach_name[0] && m->attach &&
+                     m->attach_len > 0;
+    if (has_attach) {
+        char boundary[64];
+        snprintf(boundary, sizeof boundary, "=_bokf_%s", rhex);
+        char *fname = sanitize_dup(m->attach_name);
+        const char *body = m->body ? m->body : "";
+        size_t body_len = strlen(body);
+
+        buf_appendf(out, "Content-Type: multipart/mixed; boundary=\"%s\"\r\n",
+                    boundary);
+        buf_appendf(out, "\r\n--%s\r\n", boundary);
+        buf_append_str(out, "Content-Type: text/plain; charset=utf-8\r\n");
+        buf_append_str(out, "Content-Transfer-Encoding: base64\r\n");
+        buf_append(out, "\r\n", 2);
+        append_b64_wrapped(out, (const unsigned char *)body, body_len);
+        buf_appendf(out, "--%s\r\n", boundary);
+        buf_append_str(out, "Content-Type: application/pdf; name=\"");
+        append_quoted_param(out, fname);
+        buf_append_str(out, "\"\r\n");
+        buf_append_str(out, "Content-Transfer-Encoding: base64\r\n");
+        buf_append_str(out, "Content-Disposition: attachment; filename=\"");
+        append_quoted_param(out, fname);
+        buf_append_str(out, "\"\r\n\r\n");
+        append_b64_wrapped(out, m->attach, m->attach_len);
+        buf_appendf(out, "--%s--\r\n", boundary);
+        free(fname);
+    } else {
+        const char *body = m->body ? m->body : "";
+        size_t body_len = strlen(body);
+        buf_append_str(out, "Content-Type: text/plain; charset=utf-8\r\n");
+        buf_append_str(out, "Content-Transfer-Encoding: base64\r\n");
+        buf_append(out, "\r\n", 2);
+        append_b64_wrapped(out, (const unsigned char *)body, body_len);
+    }
+    return 0;
+}
+
+static int conn_write_dotstuffed(struct smtp_conn *c, const unsigned char *data,
+                                 size_t n, char *err, size_t errlen)
+{
+    size_t start = 0;
+    while (start < n) {
+        const unsigned char *nl = memchr(data + start, '\n', n - start);
+        size_t end = nl ? (size_t)(nl - data) + 1 : n;
+        if (data[start] == '.') {
+            if (conn_write(c, ".", 1, err, errlen) != 0)
+                return -1;
+        }
+        if (conn_write(c, data + start, end - start, err, errlen) != 0)
+            return -1;
+        start = end;
+    }
+    return 0;
+}
+
+int smtp_send(const struct smtp_message *m, char *err, size_t errlen)
+{
+    if (err && errlen)
+        err[0] = '\0';
+    if (!m) {
+        set_err(err, errlen, "smtp: no message");
+        return -1;
+    }
+    if (!m->host || !m->host[0]) {
+        set_err(err, errlen, "smtp: no host");
+        return -1;
+    }
+    if (!m->from || !m->from[0]) {
+        set_err(err, errlen, "smtp: no from address");
+        return -1;
+    }
+    if (!m->to || !m->to[0]) {
+        set_err(err, errlen, "smtp: no to address");
+        return -1;
+    }
+    if (m->port <= 0 || m->port > 65535) {
+        set_err(err, errlen, "smtp: invalid port");
+        return -1;
+    }
+    const char *security = m->security ? m->security : "plain";
+    int use_tls = strcmp(security, "tls") == 0;
+    int use_starttls = strcmp(security, "starttls") == 0;
+    int use_plain = strcmp(security, "plain") == 0;
+    if (!use_tls && !use_starttls && !use_plain) {
+        set_err(err, errlen, "smtp: unknown security mode \"%s\"", security);
+        return -1;
+    }
+
+    char from[512];
+    char to[512];
+    if (normalize_addr(m->from, from, sizeof from) != 0 ||
+        normalize_addr(m->to, to, sizeof to) != 0) {
+        set_err(err, errlen, "smtp: invalid address");
+        return -1;
+    }
+
+    int ret = -1;
+    struct smtp_conn c;
+    memset(&c, 0, sizeof c);
+    c.fd = -1;
+    struct buf message;
+    buf_init(&message);
+    struct buf caps;
+    buf_init(&caps);
+
+    if (tcp_connect(&c, m->host, m->port, err, errlen) != 0)
+        goto out;
+    if (use_tls && tls_start(&c, m->host, err, errlen) != 0)
+        goto out;
+    if (conn_expect(&c, 220, "greeting", err, errlen) != 0)
+        goto out;
+
+    char hostname[256];
+    ehlo_name(hostname, sizeof hostname);
+    if (smtp_ehlo(&c, hostname, &caps, err, errlen) != 0)
+        goto out;
+
+    if (use_starttls) {
+        if (conn_line(&c, "STARTTLS", err, errlen) != 0 ||
+            conn_expect(&c, 220, "STARTTLS", err, errlen) != 0)
+            goto out;
+        if (tls_start(&c, m->host, err, errlen) != 0)
+            goto out;
+        if (smtp_ehlo(&c, hostname, &caps, err, errlen) != 0)
+            goto out;
+    }
+
+    if (smtp_auth(&c, m, (const char *)caps.p, err, errlen) != 0)
+        goto out;
+
+    char cmd[1200];
+    int n = snprintf(cmd, sizeof cmd, "MAIL FROM:<%s>", from);
+    if (n < 0 || (size_t)n >= sizeof cmd) {
+        set_err(err, errlen, "smtp: from address too long");
+        goto out;
+    }
+    if (conn_line(&c, cmd, err, errlen) != 0 ||
+        conn_expect(&c, 250, "MAIL FROM", err, errlen) != 0)
+        goto out;
+
+    n = snprintf(cmd, sizeof cmd, "RCPT TO:<%s>", to);
+    if (n < 0 || (size_t)n >= sizeof cmd) {
+        set_err(err, errlen, "smtp: to address too long");
+        goto out;
+    }
+    if (conn_line(&c, cmd, err, errlen) != 0)
+        goto out;
+    struct smtp_reply r;
+    if (conn_read_reply(&c, &r, err, errlen) != 0)
+        goto out;
+    if (r.code != 250 && r.code != 251) {
+        if (r.text[0])
+            set_err(err, errlen, "RCPT TO: server said %d %s", r.code,
+                    r.text);
+        else
+            set_err(err, errlen, "RCPT TO: server said %d", r.code);
+        goto out;
+    }
+
+    if (conn_line(&c, "DATA", err, errlen) != 0 ||
+        conn_expect(&c, 354, "DATA", err, errlen) != 0)
+        goto out;
+
+    if (build_message(m, from, to, &message, err, errlen) != 0)
+        goto out;
+    if (conn_write_dotstuffed(&c, message.p, message.len, err, errlen) != 0)
+        goto out;
+    if (conn_write(&c, ".\r\n", 3, err, errlen) != 0 ||
+        conn_expect(&c, 250, "message", err, errlen) != 0)
+        goto out;
+
+    if (conn_line(&c, "QUIT", NULL, 0) == 0)
+        (void)conn_read_reply(&c, &r, NULL, 0);
+
+    ret = 0;
+
+out:
+    buf_free(&caps);
+    buf_free(&message);
+    conn_close(&c);
+    return ret;
+}
diff --git a/src/smtp.h b/src/smtp.h
new file mode 100644
index 0000000..a6c4a34
--- /dev/null
+++ b/src/smtp.h
@@ -0,0 +1,24 @@
+#ifndef BOKF_SMTP_H
+#define BOKF_SMTP_H
+
+#include <stddef.h>
+
+struct smtp_message {
+    const char *host;
+    int port;
+    const char *security;      /* "tls" (implicit), "starttls", "plain" */
+    const char *user;          /* NULL/empty = no AUTH */
+    const char *password;
+    const char *from;          /* envelope + From address */
+    const char *from_name;     /* display name, may be NULL */
+    const char *to;
+    const char *subject;
+    const char *body;          /* UTF-8 text body */
+    const char *attach_name;   /* NULL -> text-only */
+    const unsigned char *attach;
+    size_t attach_len;
+};
+
+int smtp_send(const struct smtp_message *m, char *err, size_t errlen);
+
+#endif