diff --git a/HISTORY.rst b/HISTORY.rst
index e7a2169b23..23977f1943 100644
--- a/HISTORY.rst
+++ b/HISTORY.rst
@@ -153,7 +153,8 @@
   django_gpg app.
 - Updated the django_gpg app to work with the latest
   version of the python-gnupg package (0.4.3).
-
+- Set sensible default path for binaries by detecting
+  the operating system.
 
 3.1.9 (2018-11-01)
 ==================
diff --git a/mayan/apps/converter/literals.py b/mayan/apps/converter/literals.py
index f631e9bb58..3f36cf6500 100644
--- a/mayan/apps/converter/literals.py
+++ b/mayan/apps/converter/literals.py
@@ -1,14 +1,21 @@
 from __future__ import unicode_literals
 
+import platform
+
 CHUNK_SIZE = 1024
 
-DEFAULT_ZOOM_LEVEL = 100
-DEFAULT_ROTATION = 0
-DEFAULT_PAGE_NUMBER = 1
-DEFAULT_PILLOW_FORMAT = 'JPEG'
-DEFAULT_LIBREOFFICE_PATH = '/usr/bin/libreoffice'
+if platform.system() == 'OpenBSD':
+    DEFAULT_LIBREOFFICE_PATH = '/usr/local/bin/libreoffice'
+    DEFAULT_PDFINFO_PATH = '/usr/local/bin/pdfinfo'
+    DEFAULT_PDFTOPPM_PATH = '/usr/local/bin/pdftoppm'
+else:
+    DEFAULT_LIBREOFFICE_PATH = '/usr/bin/libreoffice'
+    DEFAULT_PDFINFO_PATH = '/usr/bin/pdfinfo'
+    DEFAULT_PDFTOPPM_PATH = '/usr/bin/pdftoppm'
 
+DEFAULT_PAGE_NUMBER = 1
 DEFAULT_PDFTOPPM_DPI = 300
 DEFAULT_PDFTOPPM_FORMAT = 'jpeg'  # Possible values jpeg, png, tiff
-DEFAULT_PDFTOPPM_PATH = '/usr/bin/pdftoppm'
-DEFAULT_PDFINFO_PATH = '/usr/bin/pdfinfo'
+DEFAULT_PILLOW_FORMAT = 'JPEG'
+DEFAULT_ROTATION = 0
+DEFAULT_ZOOM_LEVEL = 100
diff --git a/mayan/apps/django_gpg/literals.py b/mayan/apps/django_gpg/literals.py
index 108a94bb6b..9567ea6987 100644
--- a/mayan/apps/django_gpg/literals.py
+++ b/mayan/apps/django_gpg/literals.py
@@ -1,8 +1,14 @@
 from __future__ import unicode_literals
 
+import platform
+
 from django.utils.translation import ugettext_lazy as _
 
-DEFAULT_GPG_PATH = '/usr/bin/gpg1'
+if platform.system() == 'OpenBSD':
+    DEFAULT_GPG_PATH = '/usr/local/bin/gpg'
+else:
+    DEFAULT_GPG_PATH = '/usr/bin/gpg1'
+
 DEFAULT_SETTING_GPG_BACKEND = 'mayan.apps.django_gpg.classes.PythonGNUPGBackend'
 
 ERROR_MSG_BAD_PASSPHRASE = 'BAD_PASSPHRASE'
diff --git a/mayan/apps/document_parsing/literals.py b/mayan/apps/document_parsing/literals.py
new file mode 100644
index 0000000000..4de1072ce4
--- /dev/null
+++ b/mayan/apps/document_parsing/literals.py
@@ -0,0 +1,8 @@
+from __future__ import unicode_literals
+
+import platform
+
+if platform.system() == 'OpenBSD':
+    DEFAULT_PDFTOTEXT_PATH = '/usr/local/bin/pdftotext'
+else:
+    DEFAULT_PDFTOTEXT_PATH = '/usr/bin/pdftotext'
diff --git a/mayan/apps/document_parsing/settings.py b/mayan/apps/document_parsing/settings.py
index 1e9dd9f368..fd920cafcc 100644
--- a/mayan/apps/document_parsing/settings.py
+++ b/mayan/apps/document_parsing/settings.py
@@ -4,6 +4,8 @@ from django.utils.translation import ugettext_lazy as _
 
 from mayan.apps.smart_settings import Namespace
 
+from .literals import DEFAULT_PDFTOTEXT_PATH
+
 namespace = Namespace(name='document_parsing', label=_('Document parsing'))
 
 setting_auto_parsing = namespace.add_setting(
@@ -14,7 +16,7 @@ setting_auto_parsing = namespace.add_setting(
 )
 setting_pdftotext_path = namespace.add_setting(
     global_name='DOCUMENT_PARSING_PDFTOTEXT_PATH',
-    default='/usr/bin/pdftotext',
+    default=DEFAULT_PDFTOTEXT_PATH,
     help_text=_(
         'File path to poppler\'s pdftotext program used to extract text '
         'from PDF files.'
diff --git a/mayan/apps/sources/literals.py b/mayan/apps/sources/literals.py
index ee01737193..40097ba537 100644
--- a/mayan/apps/sources/literals.py
+++ b/mayan/apps/sources/literals.py
@@ -1,7 +1,14 @@
 from __future__ import unicode_literals
 
+import platform
+
 from django.utils.translation import ugettext_lazy as _
 
+if platform.system() == 'OpenBSD':
+    DEFAULT_SCANIMAGE_PATH = '/usr/local/bin/scanimage'
+else:
+    DEFAULT_SCANIMAGE_PATH = '/usr/bin/scanimage'
+
 DEFAULT_IMAP_MAILBOX = 'INBOX'
 DEFAULT_INTERVAL = 600
 DEFAULT_METADATA_ATTACHMENT_NAME = 'metadata.yaml'
diff --git a/mayan/apps/sources/settings.py b/mayan/apps/sources/settings.py
index f35e989e67..4bf8778ac7 100644
--- a/mayan/apps/sources/settings.py
+++ b/mayan/apps/sources/settings.py
@@ -7,10 +7,12 @@ from django.utils.translation import ugettext_lazy as _
 
 from mayan.apps.smart_settings import Namespace
 
+from .literals import DEFAULT_SCANIMAGE_PATH
+
 namespace = Namespace(name='sources', label=_('Sources'))
 
 setting_scanimage_path = namespace.add_setting(
-    global_name='SOURCES_SCANIMAGE_PATH', default='/usr/bin/scanimage',
+    global_name='SOURCES_SCANIMAGE_PATH', default=DEFAULT_SCANIMAGE_PATH,
     help_text=_(
         'File path to the scanimage program used to control image scanners.'
     ),