diff --git a/src/rp/cli.py b/src/rp/cli.py
index 8a151cd..4501c47 100644
--- a/src/rp/cli.py
+++ b/src/rp/cli.py
@@ -10,6 +10,7 @@ import typer
 from rich.console import Console
 
 from rp import __author__, __license__, __version__
+from rp.debug import env_debug_enabled, log_debug, make_debug_logger
 from rp.detect import detect_type
 from rp.render import RenderOptions, render
 
@@ -95,13 +96,16 @@ def main(
         version: Show version and exit.
     """
     console = Console()
+    debug = make_debug_logger(Console(stderr=True), env_debug_enabled())
 
     if file is None or str(file) == "-":
+        log_debug(debug, "input: reading from stdin")
         if sys.stdin.isatty():
             console.print("[dim]Reading from stdin. Press Ctrl+D to end.[/dim]")
         content = sys.stdin.read()
         file_path = None
     else:
+        log_debug(debug, f"input: reading file {str(file)!r}")
         if not file.exists():
             console.print(f"[red]Error:[/red] File not found: {file}")
             raise typer.Exit(code=1)
@@ -127,12 +131,14 @@ def main(
         content=content,
         explicit_type=file_type,
         guess_content=guess_content,
+        debug=debug,
     )
 
     options = RenderOptions(
         theme=theme,
         line_numbers=line_numbers,
         pager=pager,
+        debug=debug,
     )
     render(content, file_type, console, options)
 
diff --git a/src/rp/debug.py b/src/rp/debug.py
new file mode 100644
index 0000000..d15d574
--- /dev/null
+++ b/src/rp/debug.py
@@ -0,0 +1,40 @@
+"""Debug logging helpers for rp."""
+
+from __future__ import annotations
+
+import os
+from collections.abc import Callable, Mapping
+
+from rich.console import Console
+from rich.text import Text
+
+DEBUG_ENV_VAR = "RP_DEBUG"
+_FALSE_DEBUG_VALUES = {"", "0", "false", "no", "off"}
+
+type DebugLogger = Callable[[str], None]
+
+
+def env_debug_enabled(env: Mapping[str, str] | None = None) -> bool:
+    """Return whether debug logging is enabled via ``RP_DEBUG``."""
+    source = os.environ if env is None else env
+    value = source.get(DEBUG_ENV_VAR)
+    if value is None:
+        return False
+    return value.strip().lower() not in _FALSE_DEBUG_VALUES
+
+
+def make_debug_logger(console: Console, enabled: bool) -> DebugLogger | None:
+    """Return a console-backed debug logger when debug mode is enabled."""
+    if not enabled:
+        return None
+
+    def _log(message: str) -> None:
+        console.print(Text.assemble(("[rp debug] ", "dim"), message))
+
+    return _log
+
+
+def log_debug(debug: DebugLogger | None, message: str) -> None:
+    """Emit a debug line when a debug logger is configured."""
+    if debug is not None:
+        debug(message)
diff --git a/src/rp/detect.py b/src/rp/detect.py
index a53bb47..ba5d832 100644
--- a/src/rp/detect.py
+++ b/src/rp/detect.py
@@ -10,6 +10,8 @@ from pathlib import Path
 from pygments.lexers import guess_lexer
 from pygments.util import ClassNotFound
 
+from rp.debug import DebugLogger, log_debug
+
 EXTENSION_MAP: dict[str, str] = {
     ".md": "markdown",
     ".json": "json",
@@ -182,11 +184,15 @@ def _detect_shebang(content: str) -> str | None:
     return _SHEBANG_MAP.get(program)
 
 
-def _detect_pygments_content(content: str) -> str | None:
+def _detect_pygments_content(
+    content: str,
+    debug: DebugLogger | None = None,
+) -> str | None:
     """Return a lexer guessed from content when Pygments is confident."""
     try:
         lexer = guess_lexer(content)
     except ClassNotFound:
+        log_debug(debug, "type: Pygments could not guess a lexer from content")
         return None
 
     aliases: list[str] = getattr(lexer, "aliases", [])
@@ -194,8 +200,29 @@ def _detect_pygments_content(content: str) -> str | None:
     analyse_text = getattr(lexer, "analyse_text", None)
     score_value = analyse_text(content) if callable(analyse_text) else 0.0
     score = float(score_value) if isinstance(score_value, Real) else 0.0
-    if alias == "text" or score < 0.5:
+
+    guessed = alias if alias is not None else lexer.__class__.__name__
+    log_debug(debug, f"type: content guess -> lexer={guessed!r}, score={score:.3f}")
+
+    if alias is None:
+        log_debug(debug, "type: rejected content guess because the lexer has no alias")
         return None
+
+    if alias == "text":
+        log_debug(
+            debug,
+            "type: rejected content guess because the lexer resolved to plain text",
+        )
+        return None
+
+    if score < 0.5:
+        log_debug(
+            debug,
+            "type: rejected content guess because the score is below 0.500",
+        )
+        return None
+
+    log_debug(debug, f"type: inferred {alias!r} from heuristic content guessing")
     return alias
 
 
@@ -204,6 +231,7 @@ def detect_type(
     content: str | None = None,
     explicit_type: str | None = None,
     guess_content: bool = False,
+    debug: DebugLogger | None = None,
 ) -> str:
     """Detect the file type for syntax highlighting.
 
@@ -221,25 +249,32 @@ def detect_type(
         content: File content for JSON detection.
         explicit_type: Override auto-detection with explicit type.
         guess_content: Enable heuristic content-based lexer guessing.
+        debug: Optional debug logger for inference details.
 
     Returns:
         Pygments lexer name for the detected file type.
     """
     if explicit_type is not None:
+        log_debug(debug, f"type: using explicit override {explicit_type!r}")
         return explicit_type
 
     if path is not None:
         p = Path(path)
         name = p.name
         if name in _FILENAME_MAP:
-            return _FILENAME_MAP[name]
+            detected = _FILENAME_MAP[name]
+            log_debug(debug, f"type: inferred {detected!r} from filename {name!r}")
+            return detected
         suffix = p.suffix.lower()
         if suffix in EXTENSION_MAP:
-            return EXTENSION_MAP[suffix]
+            detected = EXTENSION_MAP[suffix]
+            log_debug(debug, f"type: inferred {detected!r} from extension {suffix!r}")
+            return detected
 
     if content is not None:
         shebang_type = _detect_shebang(content)
         if shebang_type is not None:
+            log_debug(debug, f"type: inferred {shebang_type!r} from shebang")
             return shebang_type
 
         stripped = content.strip()
@@ -249,13 +284,17 @@ def detect_type(
         ):
             try:
                 json.loads(stripped)
+                log_debug(debug, "type: inferred 'json' from JSON content")
                 return "json"
             except (json.JSONDecodeError, ValueError):
-                pass
+                log_debug(debug, "type: JSON-like content failed to parse")
 
         if guess_content:
-            pygments_type = _detect_pygments_content(content)
+            pygments_type = _detect_pygments_content(content, debug=debug)
             if pygments_type is not None:
                 return pygments_type
+        else:
+            log_debug(debug, "type: skipped heuristic content guessing")
 
+    log_debug(debug, "type: fell back to 'text'")
     return "text"
diff --git a/src/rp/pager.py b/src/rp/pager.py
index 6f5331a..deca72a 100644
--- a/src/rp/pager.py
+++ b/src/rp/pager.py
@@ -9,8 +9,10 @@ import subprocess
 
 from rich.pager import Pager, SystemPager
 
+from rp.debug import DebugLogger, log_debug
 
-def _mouse_capable_less() -> str | None:
+
+def _mouse_capable_less(debug: DebugLogger | None = None) -> str | None:
     """Return a ``less`` path that likely supports ``--mouse``.
 
     Mouse support was added in ``less`` 543. This probe is best-effort: it
@@ -24,6 +26,7 @@ def _mouse_capable_less() -> str | None:
     """
     less = shutil.which("less")
     if less is None:
+        log_debug(debug, "pager: 'less' was not found")
         return None
 
     try:
@@ -31,16 +34,21 @@ def _mouse_capable_less() -> str | None:
             [less, "--version"], capture_output=True, text=True, timeout=5
         )
     except (subprocess.TimeoutExpired, OSError):
+        log_debug(debug, "pager: failed to probe the installed 'less' binary")
         return None
 
     version_str = result.stdout or result.stderr or ""
     match = re.search(r"\bless\s+(\d+)\b", version_str, re.IGNORECASE)
     if match is None:
+        log_debug(debug, "pager: could not parse the installed 'less' version")
         return None
 
-    if int(match.group(1)) < 543:
+    version = int(match.group(1))
+    if version < 543:
+        log_debug(debug, f"pager: installed 'less' {version} is too old for --mouse")
         return None
 
+    log_debug(debug, f"pager: using 'less' {version} from {less!r}")
     return less
 
 
@@ -53,29 +61,41 @@ class MousePager(Pager):
     trigger a second pager session.
     """
 
+    def __init__(self, debug: DebugLogger | None = None) -> None:
+        """Initialize the pager with an optional debug logger."""
+        self._debug = debug
+
     def show(self, content: str) -> None:
         """Display rendered content in ``less -R --mouse`` when possible.
 
         Args:
             content: Fully rendered text from Rich.
         """
-        less = _mouse_capable_less()
+        less = _mouse_capable_less(self._debug)
         if less is None:
+            log_debug(self._debug, "pager: falling back to Rich's SystemPager")
             SystemPager().show(content)
             return
 
         try:
+            log_debug(self._debug, "pager: launching 'less -R --mouse'")
             result = subprocess.run(
                 [less, "-R", "--mouse"],
                 input=content,
                 text=True,
             )
         except OSError:
+            log_debug(self._debug, "pager: failed to launch 'less', using SystemPager")
             SystemPager().show(content)
             return
 
         if result.returncode in (-signal.SIGINT, 128 + signal.SIGINT):
+            log_debug(self._debug, "pager: interrupted by user")
             return
 
         if result.returncode != 0:
+            log_debug(
+                self._debug,
+                f"pager: 'less' exited with status {result.returncode}, using SystemPager",
+            )
             SystemPager().show(content)
diff --git a/src/rp/render.py b/src/rp/render.py
index 26fbf29..d74133b 100644
--- a/src/rp/render.py
+++ b/src/rp/render.py
@@ -10,6 +10,7 @@ from rich.markdown import Markdown
 from rich.padding import Padding
 from rich.syntax import Syntax
 
+from rp.debug import DebugLogger, log_debug
 from rp.pager import MousePager
 
 
@@ -21,11 +22,13 @@ class RenderOptions:
         theme: Pygments color theme name.
         line_numbers: Show line numbers. ``None`` enables them for code only.
         pager: Use pager for output. ``None`` auto-detects terminal output.
+        debug: Optional debug logger for render and pager decisions.
     """
 
     theme: str = "monokai"
     line_numbers: bool | None = None
     pager: bool | None = None
+    debug: DebugLogger | None = None
 
 
 _MARKDOWN_TYPES: set[str] = {"markdown", "md"}
@@ -49,12 +52,27 @@ def render(
     line_numbers = options.line_numbers
     if line_numbers is None:
         line_numbers = file_type not in _MARKDOWN_TYPES and file_type not in _JSON_TYPES
+        log_debug(
+            options.debug,
+            f"render: auto-set line_numbers={line_numbers} for {file_type!r}",
+        )
 
     use_pager = options.pager
     if use_pager is None:
         import sys
 
-        use_pager = sys.stdout.isatty()
+        stdout_is_tty = sys.stdout.isatty()
+        use_pager = stdout_is_tty
+        log_debug(
+            options.debug,
+            f"pager: auto-detected {'enabled' if use_pager else 'disabled'} "
+            f"because stdout is {'a' if stdout_is_tty else 'not a'} TTY",
+        )
+    else:
+        log_debug(
+            options.debug,
+            f"pager: explicitly {'enabled' if use_pager else 'disabled'}",
+        )
 
     renderable: RenderableType
     if file_type in _MARKDOWN_TYPES:
@@ -63,6 +81,7 @@ def render(
         try:
             renderable = RichJSON(content)
         except (SyntaxError, ValueError):
+            log_debug(options.debug, "render: invalid JSON, falling back to syntax")
             renderable = Syntax(
                 content, "json", theme=options.theme, line_numbers=line_numbers
             )
@@ -72,6 +91,10 @@ def render(
                 content, file_type, theme=options.theme, line_numbers=line_numbers
             )
         except Exception:
+            log_debug(
+                options.debug,
+                f"render: unknown lexer {file_type!r}, falling back to plain text",
+            )
             renderable = Syntax(
                 content, "text", theme=options.theme, line_numbers=line_numbers
             )
@@ -79,7 +102,9 @@ def render(
     padded = Padding(renderable, (1, 2))
 
     if use_pager:
-        with console.pager(pager=MousePager(), styles=True):
+        log_debug(options.debug, "pager: opening pager")
+        with console.pager(pager=MousePager(debug=options.debug), styles=True):
             console.print(padded)
     else:
+        log_debug(options.debug, "pager: writing directly to the console")
         console.print(padded)
diff --git a/tests/test_cli.py b/tests/test_cli.py
index 2490e32..ea94f46 100644
--- a/tests/test_cli.py
+++ b/tests/test_cli.py
@@ -75,6 +75,7 @@ class TestFileInput:
             content="x = 1\n",
             explicit_type=None,
             guess_content=False,
+            debug=None,
         )
 
     def test_render_called_with_correct_options(self, tmp_file) -> None:
@@ -182,8 +183,41 @@ class TestStdinInput:
             content="hello\n",
             explicit_type=None,
             guess_content=False,
+            debug=None,
         )
 
+    def test_debug_env_enables_debug_logger(self) -> None:
+        with patch("rp.cli.detect_type") as mock_detect_type:
+            mock_detect_type.return_value = "text"
+            with patch("rp.cli.render"):
+                runner.invoke(
+                    app, ["--no-pager"], input="hello\n", env={"RP_DEBUG": "1"}
+                )
+
+        _, kwargs = mock_detect_type.call_args
+        assert kwargs["debug"] is not None
+
+    def test_debug_output_stays_on_stderr(self, tmp_file) -> None:
+        file = tmp_file("# Hello\n", suffix=".md")
+
+        result = runner.invoke(app, [str(file), "--no-pager"], env={"RP_DEBUG": "1"})
+        normalized_stderr = result.stderr.replace("\n", "")
+
+        assert result.exit_code == 0
+        assert "[rp debug]" not in result.stdout
+        assert "Hello" in result.stdout
+        assert "[rp debug] input: reading file" in result.stderr
+        assert repr(str(file)) in normalized_stderr
+        assert (
+            "[rp debug] type: inferred 'markdown' from extension '.md'" in result.stderr
+        )
+        assert (
+            "[rp debug] render: auto-set line_numbers=False for 'markdown'"
+            in result.stderr
+        )
+        assert "[rp debug] pager: explicitly disabled" in result.stderr
+        assert "[rp debug] pager: writing directly to the console" in result.stderr
+
     def test_stdin_shows_tty_prompt(self) -> None:
         """When stdin is a TTY and no input is piped, show the reading hint."""
         with patch("rp.cli.sys.stdin.isatty", return_value=True):
diff --git a/tests/test_debug.py b/tests/test_debug.py
new file mode 100644
index 0000000..3277a81
--- /dev/null
+++ b/tests/test_debug.py
@@ -0,0 +1,60 @@
+"""Tests for debug helpers."""
+
+from __future__ import annotations
+
+import io
+
+from rich.console import Console
+
+from rp.debug import DEBUG_ENV_VAR, env_debug_enabled, log_debug, make_debug_logger
+
+
+class TestEnvDebugEnabled:
+    """Environment-based debug mode toggles."""
+
+    def test_disabled_by_default(self) -> None:
+        assert env_debug_enabled({}) is False
+
+    def test_false_like_values_disable_debug(self) -> None:
+        for value in ["", "0", "false", "no", "off"]:
+            assert env_debug_enabled({DEBUG_ENV_VAR: value}) is False
+
+    def test_false_like_values_are_trimmed_and_case_insensitive(self) -> None:
+        for value in [" False ", "\tNO\n", " Off "]:
+            assert env_debug_enabled({DEBUG_ENV_VAR: value}) is False
+
+    def test_truthy_values_enable_debug(self) -> None:
+        assert env_debug_enabled({DEBUG_ENV_VAR: "1"}) is True
+        assert env_debug_enabled({DEBUG_ENV_VAR: "true"}) is True
+
+    def test_truthy_values_are_trimmed_and_case_insensitive(self) -> None:
+        for value in [" TRUE ", " Yes ", "\ton\n"]:
+            assert env_debug_enabled({DEBUG_ENV_VAR: value}) is True
+
+
+class TestMakeDebugLogger:
+    """Console-backed debug logger output."""
+
+    def test_logs_visible_prefix(self) -> None:
+        stream = io.StringIO()
+        console = Console(file=stream, force_terminal=False)
+        logger = make_debug_logger(console, enabled=True)
+
+        assert logger is not None
+        logger("hello")
+
+        assert stream.getvalue() == "[rp debug] hello\n"
+
+
+class TestLogDebug:
+    """Nil-safe debug logger forwarding."""
+
+    def test_noop_when_logger_is_none(self) -> None:
+        log_debug(None, "hello")
+
+    def test_forwards_to_logger(self) -> None:
+        messages: list[str] = []
+
+        log_debug(messages.append, "hello")
+
+        assert messages == ["hello"]
diff --git a/tests/test_detect.py b/tests/test_detect.py
index b000712..021f9c4 100644
--- a/tests/test_detect.py
+++ b/tests/test_detect.py
@@ -198,6 +198,30 @@ class TestGuessContent:
         assert detect_type(content=sample_json, guess_content=True) == "json"
 
 
+class TestDebugLogging:
+    """Debug logging describes inference decisions."""
+
+    def test_logs_extension_source(self) -> None:
+        messages: list[str] = []
+
+        assert detect_type(path="script.py", debug=messages.append) == "python"
+        assert messages == ["type: inferred 'python' from extension '.py'"]
+
+    def test_logs_content_guess_and_score(self) -> None:
+        messages: list[str] = []
+        diff = "--- a/file\n+++ b/file\n@@ -1 +1 @@\n-old\n+new\n"
+
+        assert (
+            detect_type(content=diff, guess_content=True, debug=messages.append)
+            == "diff"
+        )
+        assert any(
+            "type: content guess -> lexer='diff', score=" in message
+            for message in messages
+        )
+        assert "type: inferred 'diff' from heuristic content guessing" in messages
+
+
 class TestFallback:
     """Priority 7: fallback to 'text'."""
 
diff --git a/tests/test_pager.py b/tests/test_pager.py
index 799e5a0..02ca196 100644
--- a/tests/test_pager.py
+++ b/tests/test_pager.py
@@ -25,6 +25,14 @@ class TestMouseCapableLess:
         with patch("rp.pager.shutil.which", return_value=None):
             assert _mouse_capable_less() is None
 
+    def test_logs_less_not_found(self) -> None:
+        messages: list[str] = []
+
+        with patch("rp.pager.shutil.which", return_value=None):
+            assert _mouse_capable_less(messages.append) is None
+
+        assert messages == ["pager: 'less' was not found"]
+
     def test_returns_none_when_less_too_old(self) -> None:
         with patch("rp.pager.shutil.which", return_value="/usr/bin/less"):
             mock_result = MagicMock()
@@ -99,6 +107,19 @@ class TestMousePager:
 
                 mock_instance.show.assert_called_once_with("content")
 
+    def test_logs_system_pager_fallback(self) -> None:
+        messages: list[str] = []
+        pager = MousePager(debug=messages.append)
+
+        with patch("rp.pager._mouse_capable_less", return_value=None):
+            with patch("rp.pager.SystemPager") as mock_system_pager:
+                mock_instance = MagicMock()
+                mock_system_pager.return_value = mock_instance
+
+                pager.show("content")
+
+        assert messages == ["pager: falling back to Rich's SystemPager"]
+
     def test_uses_less_when_available(self) -> None:
         pager = MousePager()
         mock_result = MagicMock()
diff --git a/tests/test_render.py b/tests/test_render.py
index d9c92fe..4781a14 100644
--- a/tests/test_render.py
+++ b/tests/test_render.py
@@ -35,6 +35,10 @@ class TestRenderOptions:
         assert opts.line_numbers is True
         assert opts.pager is False
 
+    def test_default_debug_is_none(self) -> None:
+        opts = RenderOptions()
+        assert opts.debug is None
+
 
 class TestRenderMarkdown:
     """Markdown rendering."""
@@ -238,6 +242,18 @@ class TestPagerBehavior:
         assert len(capture_console.file.getvalue()) > 0
         mock_pager.assert_not_called()
 
+    def test_logs_auto_pager_decision(
+        self, capture_console, sample_python: str
+    ) -> None:
+        messages: list[str] = []
+        opts = RenderOptions(pager=None, debug=messages.append)
+
+        with patch("sys.stdout.isatty", return_value=False):
+            render(sample_python, "python", capture_console, opts)
+
+        assert "pager: auto-detected disabled because stdout is not a TTY" in messages
+        assert "pager: writing directly to the console" in messages
+
 
 class TestPadding:
     """Rendered output is wrapped in padding."""