diff --git a/pytest.ini b/pytest.ini
index 6c2404056..31a294ca6 100644
--- a/pytest.ini
+++ b/pytest.ini
@@ -4,15 +4,10 @@
 [pytest]
 # In general, all warnings are treated as errors. Here are the exceptions:
 #   1- decodestring: https://github.com/rthalley/dnspython/issues/338
-#   2- ignore our own TLS-SNI-01 warning
-#   3- ignore warn for importing abstract classes from collections instead of collections.abc,
+#   2- ignore warn for importing abstract classes from collections instead of collections.abc,
 #      too much third party dependencies are still relying on this behavior,
 #      but it should be corrected to allow Certbot compatiblity with Python >= 3.8
-#   4- ipdb uses deprecated functionality of IPython. See
-#      https://github.com/gotcha/ipdb/issues/144.
 filterwarnings =
     error
     ignore:decodestring:DeprecationWarning
     ignore:.*collections\.abc:DeprecationWarning
-    ignore:The `color_scheme` argument is deprecated:DeprecationWarning:IPython.*
-    ignore:.*get_systemd_os_info:DeprecationWarning
diff --git a/tools/dev_constraints.txt b/tools/dev_constraints.txt
index d5d78c96a..a16a9d680 100644
--- a/tools/dev_constraints.txt
+++ b/tools/dev_constraints.txt
@@ -21,7 +21,7 @@ codecov==2.0.15
 configparser==3.7.4
 contextlib2==0.6.0.post1
 coverage==4.5.4
-decorator==4.1.2
+decorator==4.4.1
 dns-lexicon==3.2.1
 dnspython==1.15.0
 docker==3.7.2
@@ -39,8 +39,8 @@ google-api-python-client==1.5.5
 httplib2==0.10.3
 imagesize==0.7.1
 importlib-metadata==0.23
-ipdb==0.10.2
-ipython==5.5.0
+ipdb==0.12.3
+ipython==5.8.0
 ipython-genutils==0.2.0
 isort==4.3.21
 Jinja2==2.9.6
@@ -59,12 +59,12 @@ ndg-httpsclient==0.3.2
 oauth2client==4.0.0
 packaging==19.2
 paramiko==2.4.2
-pathlib2==2.3.0
+pathlib2==2.3.5
 pexpect==4.7.0
-pickleshare==0.7.4
+pickleshare==0.7.5
 pkginfo==1.4.2
 pluggy==0.13.0
-prompt-toolkit==1.0.15
+prompt-toolkit==1.0.18
 ptyprocess==0.6.0
 py==1.8.0
 pyasn1==0.1.9
@@ -90,7 +90,7 @@ requests-file==1.4.2
 requests-toolbelt==0.8.0
 rsa==3.4.2
 s3transfer==0.1.11
-scandir==1.6
+scandir==1.10.0
 simplegeneric==0.8.1
 singledispatch==3.4.0.3
 snowballstemmer==1.2.1
@@ -102,13 +102,13 @@ tldextract==2.2.0
 toml==0.10.0
 tox==3.14.0
 tqdm==4.19.4
-traitlets==4.3.2
+traitlets==4.3.3
 twine==1.11.0
 typed-ast==1.4.0
 typing==3.6.4
 uritemplate==3.0.0
 virtualenv==16.6.2
-wcwidth==0.1.7
+wcwidth==0.1.8
 websocket-client==0.56.0
 wrapt==1.11.2
 zipp==0.6.0