diff --git a/docs/features/safemode.rst b/docs/features/safemode.rst
index a99cbf97..c90d30d6 100644
--- a/docs/features/safemode.rst
+++ b/docs/features/safemode.rst
@@ -16,6 +16,9 @@ Additionally, OctoPrint allows uninstalling plugins in this mode, allowing recov
 a third party plugin causes the server to not start up or the web interface to not render or function
 correctly anymore.
 
+Whenever reporting an issue with OctoPrint, please always attempt to reproduce it in safe mode as well to
+ensure it really is an issue in OctoPrint itself and now caused by one of your installed third party plugins.
+
 .. _sec-features-safemode-how:
 
 How to start OctoPrint in safe mode
@@ -23,15 +26,37 @@ How to start OctoPrint in safe mode
 
 There exist three ways to start OctoPrint in safe mode:
 
-  * since OctoPrint 1.3.2: by selecting "Restart OctoPrint in safe mode" from the "System" menu,
-    if the "Restart OctoPrint" server command has been correctly configured (see :numref:`fig-features-safemode-systemmenu`).
-  * by starting OctoPrint with the command line parameter ``--safe``, e.g. ``octoprint serve --safe``
-  * by setting the option ``server.startOnceInSafeMode`` in :ref:`config.yaml <sec-configuration-config_yaml>`
-    to ``true`` and restarting
+  * by selecting "Restart OctoPrint in safe mode" from the "System" menu,
+    if the "Restart OctoPrint" server command has been correctly configured (since OctoPrint 1.3.2,
+    see :numref:`fig-features-safemode-systemmenu`)
+  * by setting the flag ``server.startOnceInSafeMode`` in :ref:`config.yaml <sec-configuration-config_yaml>`
+    to ``true`` and restarting. To set this flag you have the following options:
+
+    * from command line run ``octoprint safemode`` (since OctoPrint 1.3.6)
+    * from command line run ``octoprint config set --bool server.startOnceInSafeMode true`` (fixed in OctoPrint 1.3.6)
+    * use the `Yamlpatcher Plugin <http://plugins.octoprint.org/plugins/yamlpatcher/>`_ and enter & apply the patch
+      ``[["set", "server.startOnceInSafeMode", true]]``
+    * edit ``config.yaml`` manually with a text editor, locate the ``server`` block if it already exists or create it
+      if it doesn't and add ``startOnceInSafeMode: true`` to it:
+
+      .. code-block:: yaml
+
+         # ...
+         server:
+           startOnceInSafeMode: true
+         # ...
+
+      Please also refer to the :ref:`YAML primer <sec-configuration-yaml>`.
+  * by starting OctoPrint with the command line parameter ``--safe``, e.g. ``octoprint serve --safe`` (don't forget to
+    shutdown OctoPrint first before doing this)
 
 The last two options will have OctoPrint enable safe mode only for the next server start - once you
 restart OctoPrint again, safe mode will be disabled again.
 
+.. note::
+
+   **OctoPi users**: For you that's ``~/oprint/bin/octoprint`` wherever it says just ``octoprint``.
+
 .. _fig-features-safemode-systemmenu:
 .. figure:: ../images/features-safemode-systemmenu.png
    :align: center
diff --git a/src/octoprint/cli/__init__.py b/src/octoprint/cli/__init__.py
index 1cc3d82e..9562b173 100644
--- a/src/octoprint/cli/__init__.py
+++ b/src/octoprint/cli/__init__.py
@@ -102,7 +102,7 @@ def standard_options(hidden=False):
 
 	options = [
 		factory("--basedir", "-b", type=click.Path(), callback=set_ctx_obj_option, is_eager=True, expose_value=False,
-		        help="Specify the basedir to use for uploads, timelapses etc."),
+		        help="Specify the basedir to use for configs, uploads, timelapses etc."),
 		factory("--config", "-c", "configfile", type=click.Path(), callback=set_ctx_obj_option, is_eager=True, expose_value=False,
 		        help="Specify the config file to use."),
 		factory("--verbose", "-v", "verbosity", count=True, callback=set_ctx_obj_option, is_eager=True, expose_value=False,
diff --git a/src/octoprint/cli/config.py b/src/octoprint/cli/config.py
index 319069a2..3554a14d 100644
--- a/src/octoprint/cli/config.py
+++ b/src/octoprint/cli/config.py
@@ -54,7 +54,7 @@ def config(ctx):
 		ctx.obj.settings = init_settings(get_ctx_obj_option(ctx, "basedir", None), get_ctx_obj_option(ctx, "configfile", None))
 	except FatalStartupError as e:
 		click.echo(e.message, err=True)
-		click.echo("There was a fatal error initializing the client.", err=True)
+		click.echo("There was a fatal error initializing the settings manager.", err=True)
 		ctx.exit(-1)
 
 
diff --git a/src/octoprint/cli/server.py b/src/octoprint/cli/server.py
index cfadc559..5789af64 100644
--- a/src/octoprint/cli/server.py
+++ b/src/octoprint/cli/server.py
@@ -125,6 +125,27 @@ def server_commands():
 	pass
 
 
+@server_commands.command(name="safemode")
+@standard_options(hidden=True)
+@click.pass_context
+def enable_safemode(ctx, **kwargs):
+	"""Sets the safe mode flag for the next start."""
+	from octoprint import init_settings, FatalStartupError
+
+	logging.basicConfig(level=logging.DEBUG if get_ctx_obj_option(ctx, "verbosity", 0) > 0 else logging.WARN)
+	try:
+		settings = init_settings(get_ctx_obj_option(ctx, "basedir", None), get_ctx_obj_option(ctx, "configfile", None))
+	except FatalStartupError as e:
+		click.echo(e.message, err=True)
+		click.echo("There was a fatal error initializing the settings manager.", err=True)
+		ctx.exit(-1)
+
+	settings.setBoolean(["server", "startOnceInSafeMode"], True)
+	settings.save()
+	
+	click.echo("Safe mode flag set, OctoPrint will start in safe mode on next restart.")
+
+
 @server_commands.command(name="serve")
 @server_options
 @standard_options(hidden=True)