s2k-cli 0.1.0__tar.gz → 0.3.0__tar.gz

{s2k_cli-0.1.0 → s2k_cli-0.3.0}/PKG-INFO

@@ -1,6 +1,6 @@
 Metadata-Version: 2.3
 Name: s2k-cli
-Version: 0.1.0
+Version: 0.3.0
 Summary: Send local files to your Kindle from the command line.
 License: MIT
 Keywords: kindle,send-to-kindle,ebook,email,cli
@@ -33,7 +33,7 @@ s2k send book.epub paper.pdf notes.docx
 ```
 
 Supported: `.pdf .epub .doc .docx .txt .rtf .html .htm .jpg .jpeg .png .gif .bmp`, up to 50 MB
-each (your email provider may allow less: Gmail rejects files above roughly 18 MB).
+each (your email provider may allow less: Gmail about 18 MB, iCloud Mail about 14 MB).
 
 ## Install
 
@@ -48,8 +48,13 @@ pipx install s2k-cli       # or: uv tool install s2k-cli
 1. **In Amazon** (*Manage Your Content and Devices → Preferences → Personal Document Settings*):
    copy your `@kindle.com` address and add the email you will send from to the *Approved Personal
    Document E-mail List*.
-2. **Gmail users:** create an app password at <https://myaccount.google.com/apppasswords>
-   (requires 2-Step Verification). Your normal Gmail password will not work.
+2. **Create the password your provider requires** — your normal password will not work:
+
+   | Provider | Password | Server (filled in by `s2k init`) |
+   |---|---|---|
+   | Gmail | [App password](https://myaccount.google.com/apppasswords) (needs 2-Step Verification) | `smtp.gmail.com`, 587, STARTTLS |
+   | iCloud Mail | App-specific password at [account.apple.com](https://account.apple.com) → Sign-In and Security (needs two-factor authentication); send from your full `@icloud.com` address | `smtp.mail.me.com`, 587, STARTTLS |
+   | Other | Your provider's SMTP password | you type it |
 3. Run the wizard in your terminal — it asks for the values, hides the password, saves them to
    `~/.config/s2k/config.env` with private permissions and offers to test the login:
    ```bash
@@ -71,6 +76,9 @@ s2k --version
 
 Exit codes: `0` success · `1` something failed (see the report) · `2` invalid configuration or usage.
 
+Files in iCloud Drive that are not downloaded yet ("Optimize Mac Storage") are downloaded
+automatically when sent, so you need a connection.
+
 "Sent" means your email provider accepted the message. If Amazon rejects it (for example, the
 sender is not approved), Amazon emails you.
 

{s2k_cli-0.1.0 → s2k_cli-0.3.0}/README.md

@@ -7,7 +7,7 @@ s2k send book.epub paper.pdf notes.docx
 ```
 
 Supported: `.pdf .epub .doc .docx .txt .rtf .html .htm .jpg .jpeg .png .gif .bmp`, up to 50 MB
-each (your email provider may allow less: Gmail rejects files above roughly 18 MB).
+each (your email provider may allow less: Gmail about 18 MB, iCloud Mail about 14 MB).
 
 ## Install
 
@@ -22,8 +22,13 @@ pipx install s2k-cli       # or: uv tool install s2k-cli
 1. **In Amazon** (*Manage Your Content and Devices → Preferences → Personal Document Settings*):
    copy your `@kindle.com` address and add the email you will send from to the *Approved Personal
    Document E-mail List*.
-2. **Gmail users:** create an app password at <https://myaccount.google.com/apppasswords>
-   (requires 2-Step Verification). Your normal Gmail password will not work.
+2. **Create the password your provider requires** — your normal password will not work:
+
+   | Provider | Password | Server (filled in by `s2k init`) |
+   |---|---|---|
+   | Gmail | [App password](https://myaccount.google.com/apppasswords) (needs 2-Step Verification) | `smtp.gmail.com`, 587, STARTTLS |
+   | iCloud Mail | App-specific password at [account.apple.com](https://account.apple.com) → Sign-In and Security (needs two-factor authentication); send from your full `@icloud.com` address | `smtp.mail.me.com`, 587, STARTTLS |
+   | Other | Your provider's SMTP password | you type it |
 3. Run the wizard in your terminal — it asks for the values, hides the password, saves them to
    `~/.config/s2k/config.env` with private permissions and offers to test the login:
    ```bash
@@ -45,6 +50,9 @@ s2k --version
 
 Exit codes: `0` success · `1` something failed (see the report) · `2` invalid configuration or usage.
 
+Files in iCloud Drive that are not downloaded yet ("Optimize Mac Storage") are downloaded
+automatically when sent, so you need a connection.
+
 "Sent" means your email provider accepted the message. If Amazon rejects it (for example, the
 sender is not approved), Amazon emails you.
 

{s2k_cli-0.1.0 → s2k_cli-0.3.0}/pyproject.toml

@@ -1,6 +1,6 @@
 [project]
 name = "s2k-cli"
-version = "0.1.0"
+version = "0.3.0"
 description = "Send local files to your Kindle from the command line."
 authors = [{ name = "Marco Fura", email = "mjfura27@gmail.com" }]
 readme = "README.md"

{s2k_cli-0.1.0 → s2k_cli-0.3.0}/src/send_2_kindle/config.py

@@ -8,8 +8,8 @@ from dotenv import dotenv_values
 from pydantic import EmailStr, Field, SecretStr, ValidationError, field_validator
 from pydantic_settings import BaseSettings, PydanticBaseSettingsSource, SettingsConfigDict
 
-from send_2_kindle import constants
 from send_2_kindle.errors import ConfigError
+from send_2_kindle.providers import GMAIL
 
 ENV_PREFIX: Final[str] = "S2K_"
 CONFIG_FILE_VARIABLE: Final[str] = "S2K_CONFIG_FILE"
@@ -33,8 +33,10 @@ def config_file_path() -> Path:
     override = os.environ.get(CONFIG_FILE_VARIABLE)
     if override:
         return Path(override).expanduser()
-    base = os.environ.get("XDG_CONFIG_HOME") or "~/.config"
-    return Path(base).expanduser() / "s2k" / "config.env"
+    xdg = os.environ.get("XDG_CONFIG_HOME", "")
+    # The XDG spec says relative values must be ignored.
+    base = Path(xdg) if xdg and Path(xdg).is_absolute() else Path("~/.config").expanduser()
+    return base / "s2k" / "config.env"
 
 
 class Settings(BaseSettings):
@@ -47,7 +49,7 @@ class Settings(BaseSettings):
     kindle_email: EmailStr
     sender_email: EmailStr
     smtp_password: SecretStr
-    smtp_host: SmtpHost = constants.GMAIL_SMTP_HOST
+    smtp_host: SmtpHost = GMAIL.host
     smtp_port: SmtpPort = 587
     smtp_security: SmtpSecurity = "starttls"
     smtp_username: str | None = None

{s2k_cli-0.1.0 → s2k_cli-0.3.0}/src/send_2_kindle/constants.py

@@ -14,6 +14,3 @@ ALLOWED_EXTENSIONS: Final[frozenset[str]] = frozenset(
 MAX_EMAIL_SIZE_BYTES: Final[int] = 50_000_000
 
 SMTP_TIMEOUT_SECONDS: Final[float] = 30.0
-
-GMAIL_SMTP_HOST: Final[str] = "smtp.gmail.com"
-GMAIL_APP_PASSWORDS_URL: Final[str] = "https://myaccount.google.com/apppasswords"

{s2k_cli-0.1.0 → s2k_cli-0.3.0}/src/send_2_kindle/mailer.py

@@ -11,6 +11,8 @@ from typing import Self
 from send_2_kindle import constants
 from send_2_kindle.config import Settings
 from send_2_kindle.errors import SendError, SmtpAuthError, SmtpConnectionError
+from send_2_kindle.providers import provider_for_host
+from send_2_kindle.validation import is_not_downloaded
 
 
 def build_message(settings: Settings, path: Path) -> EmailMessage:
@@ -35,14 +37,23 @@ def _text(value: bytes | str) -> str:
 
 def _auth_failure_message(settings: Settings) -> str:
     message = f"authentication failed for {settings.login_username} on {settings.smtp_host}"
-    if settings.smtp_host == constants.GMAIL_SMTP_HOST:
+    provider = provider_for_host(settings.smtp_host)
+    if provider is not None:
         message += (
-            ". Gmail requires an app password, not your account password: "
-            f"{constants.GMAIL_APP_PASSWORDS_URL}"
+            f". {provider.name} requires an {provider.password_name}, not your account password: "
+            f"{provider.password_url}"
         )
     return message
 
 
+def _security_hint(settings: Settings) -> str:
+    if settings.smtp_port == 465 and settings.smtp_security == "starttls":
+        return " (port 465 normally needs S2K_SMTP_SECURITY=ssl)"
+    if settings.smtp_port == 587 and settings.smtp_security == "ssl":
+        return " (port 587 normally needs S2K_SMTP_SECURITY=starttls)"
+    return ""
+
+
 def _close_quietly(smtp: smtplib.SMTP | None) -> None:
     if smtp is not None:
         smtp.close()
@@ -112,6 +123,7 @@ class KindleMailer:
             _close_quietly(smtp)
             raise SmtpConnectionError(
                 f"could not connect to {settings.smtp_host}:{settings.smtp_port}: {error}"
+                f"{_security_hint(settings)}"
             ) from error
         self._smtp = smtp
         return self
@@ -141,6 +153,10 @@ class KindleMailer:
         try:
             message = build_message(self._settings, path)
         except OSError as error:
+            if is_not_downloaded(path):
+                raise SendError(
+                    f"could not download it from iCloud (are you offline?): {error}"
+                ) from error
             raise SendError(f"could not read file: {error}") from error
         try:
             self._smtp.send_message(message)

{s2k_cli-0.1.0 → s2k_cli-0.3.0}/src/send_2_kindle/main.py

@@ -6,7 +6,7 @@ from typing import Annotated
 
 import typer
 
-from send_2_kindle import installed_version
+from send_2_kindle import constants, installed_version
 from send_2_kindle.config import load_settings
 from send_2_kindle.doctor import report, run_checks
 from send_2_kindle.errors import (
@@ -17,7 +17,8 @@ from send_2_kindle.errors import (
     SmtpConnectionError,
 )
 from send_2_kindle.mailer import KindleMailer
-from send_2_kindle.validation import validate_file
+from send_2_kindle.providers import provider_for_host
+from send_2_kindle.validation import is_not_downloaded, validate_file
 from send_2_kindle.wizard import run_wizard
 
 AMAZON_NOTE = (
@@ -67,16 +68,34 @@ def send(
         typer.secho(str(error), fg=typer.colors.RED, err=True)
         raise typer.Exit(code=2) from None
 
+    provider = provider_for_host(settings.smtp_host)
+    max_bytes = min(constants.MAX_EMAIL_SIZE_BYTES, provider.max_file_bytes) if provider else None
+    provider_name = provider.name if provider else None
+
     outcomes = [Outcome(path) for path in files]
     pending: list[Outcome] = []
     for outcome in outcomes:
         try:
-            validate_file(outcome.path)
+            validate_file(outcome.path, max_bytes=max_bytes, provider_name=provider_name)
         except FileValidationError as error:
             outcome.reason = str(error)
         else:
             pending.append(outcome)
 
+    # Download iCloud Drive files before logging in: a long download would leave the SMTP
+    # session idle, and a server that drops it would fail every remaining file.
+    ready: list[Outcome] = []
+    for outcome in pending:
+        if is_not_downloaded(outcome.path):
+            typer.echo(f'Downloading "{outcome.path.name}" from iCloud…')
+            try:
+                _fetch_from_icloud(outcome.path)
+            except OSError as error:
+                outcome.reason = f"could not download it from iCloud (are you offline?): {error}"
+                continue
+        ready.append(outcome)
+    pending = ready
+
     if pending:
         try:
             with KindleMailer(settings) as mailer:
@@ -107,6 +126,11 @@ def init() -> None:
     raise typer.Exit(code=run_wizard())
 
 
+def _fetch_from_icloud(path: Path) -> None:
+    """Reading a not-downloaded iCloud Drive file makes macOS download it."""
+    path.read_bytes()
+
+
 def _print_report(outcomes: list[Outcome]) -> None:
     width = max(len(str(outcome.path)) for outcome in outcomes)
     for outcome in outcomes:

s2k_cli-0.3.0/src/send_2_kindle/providers.py

@@ -0,0 +1,40 @@
+"""Known email providers: SMTP settings, attachment limits and where to get their passwords."""
+
+from dataclasses import dataclass, field
+from typing import Final
+
+
+@dataclass(frozen=True)
+class Provider:
+    key: str
+    name: str
+    host: str
+    port: int
+    security: str
+    # Message limits (Gmail 25 MB, iCloud 20 MB) divided by ~1.37 (base64 4/3 and CRLF line
+    # wrapping 78/76), rounded down: 18 MB → ~24.6 MB, 14 MB → ~19.2 MB.
+    max_file_bytes: int
+    password_name: str
+    password_url: str
+    aliases: tuple[str, ...] = field(default=())
+
+
+GMAIL: Final = Provider(
+    "gmail", "Gmail", "smtp.gmail.com", 587, "starttls", 18_000_000,
+    "app password", "https://myaccount.google.com/apppasswords",
+)  # fmt: skip
+ICLOUD: Final = Provider(
+    "icloud", "iCloud", "smtp.mail.me.com", 587, "starttls", 14_000_000,
+    "app-specific password", "https://account.apple.com", ("smtp.me.com", "smtp.mac.com"),
+)  # fmt: skip
+PROVIDERS: Final[tuple[Provider, ...]] = (GMAIL, ICLOUD)
+
+
+def provider_for_host(host: str) -> Provider | None:
+    """Return the provider whose SMTP server is ``host`` (case and spaces ignored)."""
+    normalized = host.strip().lower()
+    return next((p for p in PROVIDERS if normalized == p.host or normalized in p.aliases), None)
+
+
+def provider_for_key(key: str) -> Provider | None:
+    return next((provider for provider in PROVIDERS if provider.key == key), None)

{s2k_cli-0.1.0 → s2k_cli-0.3.0}/src/send_2_kindle/validation.py

@@ -3,16 +3,31 @@
 import os
 import stat
 from pathlib import Path
+from typing import Final
 
 from send_2_kindle import constants
 from send_2_kindle.errors import FileValidationError
 
+# macOS marks iCloud Drive files whose contents are not on disk yet ("Optimize Mac Storage").
+SF_DATALESS: Final[int] = 0x40000000
+
+
+def is_not_downloaded(path: Path) -> bool:
+    """True for an iCloud Drive file macOS has not downloaded; reading it triggers the download."""
+    try:
+        flags = getattr(path.stat(), "st_flags", 0)
+    except OSError:
+        return False
+    return bool(flags & SF_DATALESS)
+
 
 def _megabytes(size: int) -> float:
     return size / 1_000_000
 
 
-def validate_file(path: Path) -> None:
+def validate_file(
+    path: Path, max_bytes: int | None = None, provider_name: str | None = None
+) -> None:
     """Raise FileValidationError with a user-facing reason if ``path`` cannot be sent."""
     # stat() tells "missing" apart from "can't reach it" (Path.exists() reports both as False).
     try:
@@ -36,6 +51,8 @@ def validate_file(path: Path) -> None:
         raise FileValidationError("file is empty")
     if not os.access(path, os.R_OK):
         raise FileValidationError("file is not readable")
-    if size > constants.MAX_EMAIL_SIZE_BYTES:
-        limit = _megabytes(constants.MAX_EMAIL_SIZE_BYTES)
-        raise FileValidationError(f"file exceeds {limit:g} MB ({_megabytes(size):.1f} MB)")
+    limit_bytes = constants.MAX_EMAIL_SIZE_BYTES if max_bytes is None else max_bytes
+    if size > limit_bytes:
+        limit = f"{_megabytes(limit_bytes):g} MB"
+        where = f", the limit for {provider_name}" if provider_name else ""
+        raise FileValidationError(f"file exceeds {limit}{where} ({_megabytes(size):.1f} MB)")

{s2k_cli-0.1.0 → s2k_cli-0.3.0}/src/send_2_kindle/wizard.py

@@ -4,12 +4,11 @@ import os
 import sys
 import tempfile
 from pathlib import Path
-from typing import Any
+from typing import Annotated, Any, Literal
 
 import typer
-from pydantic import EmailStr, TypeAdapter, ValidationError
+from pydantic import BeforeValidator, EmailStr, TypeAdapter, ValidationError
 
-from send_2_kindle import constants
 from send_2_kindle.config import (
     SmtpHost,
     SmtpPort,
@@ -18,6 +17,7 @@ from send_2_kindle.config import (
     read_config_file,
 )
 from send_2_kindle.doctor import report, run_checks
+from send_2_kindle.providers import GMAIL, PROVIDERS, provider_for_host, provider_for_key
 
 INTRO = """\
 s2k init: configure Send to Kindle by email.
@@ -26,14 +26,24 @@ You will need:
   - Your Send to Kindle address: Amazon > Manage Your Content and Devices > Preferences >
     Personal Document Settings.
   - The email you send from must be on the "Approved Personal Document E-mail List" (same page).
-  - Gmail: an app password, not your account password: {url}
+{passwords}
 """
+PASSWORD_LINES = "\n".join(
+    f"  - {p.name}: an {p.password_name}, not your account password: {p.password_url}"
+    for p in PROVIDERS
+)
 HEADER = "# s2k configuration, written by `s2k init`. Keep it private (chmod 600).\n"
 
 _EMAIL: TypeAdapter[Any] = TypeAdapter(EmailStr)
 _HOST: TypeAdapter[Any] = TypeAdapter(SmtpHost)
 _PORT: TypeAdapter[Any] = TypeAdapter(SmtpPort)
 _SECURITY: TypeAdapter[Any] = TypeAdapter(SmtpSecurity)
+_PROVIDER: TypeAdapter[Any] = TypeAdapter(
+    Annotated[
+        Literal["gmail", "icloud", "other"],
+        BeforeValidator(lambda value: value.lower() if isinstance(value, str) else value),
+    ]
+)
 
 
 def _is_interactive() -> bool:
@@ -46,7 +56,11 @@ def _quote(value: str) -> str:
 
 
 def write_config(path: Path, values: dict[str, str]) -> None:
-    """Atomically write ``values`` as KEY="value" lines to ``path`` (mode 600, new dirs 700)."""
+    """Atomically write ``values`` as KEY="value" lines to ``path`` (mode 600, new dirs 700).
+
+    A symlinked config file (e.g. managed by a dotfiles repo) is kept: its target is rewritten.
+    """
+    path = path.resolve() if path.is_symlink() else path
     path.parent.mkdir(mode=0o700, parents=True, exist_ok=True)
     content = HEADER + "".join(f"{key}={_quote(value)}\n" for key, value in values.items())
     fd, temp_name = tempfile.mkstemp(dir=path.parent, prefix=".config.env.")
@@ -79,33 +93,64 @@ def _ask(text: str, adapter: TypeAdapter[Any], default: str | None) -> str:
 
 
 def _ask_password(has_current: bool) -> str | None:
-    """Return the new password, or None to keep the current one."""
-    if has_current:
-        answer = typer.prompt(
-            "SMTP password (empty keeps the current one)",
-            default="",
-            hide_input=True,
-            show_default=False,
-        )
-        return str(answer) or None
-    return str(typer.prompt("SMTP password", hide_input=True))
+    """Return the new password (typed twice), or None to keep the current one."""
+    while True:
+        if has_current:
+            answer = str(
+                typer.prompt(
+                    "SMTP password (empty keeps the current one)",
+                    default="",
+                    hide_input=True,
+                    show_default=False,
+                )
+            )
+            if not answer:
+                return None
+        else:
+            answer = str(typer.prompt("SMTP password", hide_input=True))
+        if str(typer.prompt("Repeat the SMTP password", hide_input=True)) == answer:
+            return answer
+        typer.secho("  The passwords do not match; try again.", fg=typer.colors.YELLOW)
 
 
 def _collect(current: dict[str, str]) -> dict[str, str]:
+    existing_host = current.get("S2K_SMTP_HOST")
+    known = provider_for_host(existing_host) if existing_host else GMAIL
+    choice = _ask("Email provider (gmail/icloud/other)", _PROVIDER, known.key if known else "other")
+    provider = provider_for_key(choice.lower())
+    sender_label = "Email you send from"
+    if provider is not None and provider.key == "icloud":
+        sender_label += " (your iCloud Mail address, e.g. name@icloud.com)"
     values = {
         "S2K_KINDLE_EMAIL": _ask("Send to Kindle address", _EMAIL, current.get("S2K_KINDLE_EMAIL")),
-        "S2K_SENDER_EMAIL": _ask("Email you send from", _EMAIL, current.get("S2K_SENDER_EMAIL")),
-        "S2K_SMTP_HOST": _ask(
-            "SMTP server", _HOST, current.get("S2K_SMTP_HOST", constants.GMAIL_SMTP_HOST)
-        ),
-        "S2K_SMTP_PORT": _ask("SMTP port", _PORT, current.get("S2K_SMTP_PORT", "587")),
-        "S2K_SMTP_SECURITY": _ask(
-            "Security (starttls/ssl)", _SECURITY, current.get("S2K_SMTP_SECURITY", "starttls")
-        ),
+        "S2K_SENDER_EMAIL": _ask(sender_label, _EMAIL, current.get("S2K_SENDER_EMAIL")),
     }
+    if provider is not None:
+        # Same provider as before: keep a port/security the user chose (e.g. Gmail on 465/ssl).
+        same = existing_host is not None and provider_for_host(existing_host) is provider
+        values |= {
+            "S2K_SMTP_HOST": provider.host,
+            "S2K_SMTP_PORT": current.get("S2K_SMTP_PORT", str(provider.port))
+            if same
+            else str(provider.port),
+            "S2K_SMTP_SECURITY": current.get("S2K_SMTP_SECURITY", provider.security)
+            if same
+            else provider.security,
+        }
+        typer.echo(f"  {provider.name} needs an {provider.password_name}: {provider.password_url}")
+    else:
+        values |= {
+            "S2K_SMTP_HOST": _ask("SMTP server", _HOST, current.get("S2K_SMTP_HOST", GMAIL.host)),
+            "S2K_SMTP_PORT": _ask("SMTP port", _PORT, current.get("S2K_SMTP_PORT", "587")),
+            "S2K_SMTP_SECURITY": _ask(
+                "Security (starttls/ssl)", _SECURITY, current.get("S2K_SMTP_SECURITY", "starttls")
+            ),
+        }
     password = _ask_password(bool(current.get("S2K_SMTP_PASSWORD")))
     values["S2K_SMTP_PASSWORD"] = password if password is not None else current["S2K_SMTP_PASSWORD"]
-    if current.get("S2K_SMTP_USERNAME"):
+    # A custom login belongs to its server: drop it when the server changes.
+    old_host = (existing_host or "").strip().lower()
+    if current.get("S2K_SMTP_USERNAME") and values["S2K_SMTP_HOST"].strip().lower() == old_host:
         values["S2K_SMTP_USERNAME"] = current["S2K_SMTP_USERNAME"]
     return values
 
@@ -118,7 +163,7 @@ def run_wizard() -> int:
         )
         return 2
     path = config_file_path()
-    typer.echo(INTRO.format(url=constants.GMAIL_APP_PASSWORDS_URL))
+    typer.echo(INTRO.format(passwords=PASSWORD_LINES))
     try:
         values = _collect(_read_existing(path))
     except typer.Abort: