diff --git a/Gemfile b/Gemfile
index dd921cce2b46aa237e9feb152c12671cd51278bd..fe8f4736e20a9e2b6776cd6bfb1e7644874450c6 100644
--- a/Gemfile
+++ b/Gemfile
@@ -2,7 +2,7 @@
 source 'https://rubygems.org'
 
 # List of required gems
-gem 'jekyll', '~> 4.1.1'
+gem 'jekyll', '~> 4.2.0'
 gem 'jekyll-paginate', '~> 1.1.0'
 gem 'rouge', '~> 3.26.0'
 gem 'jekyll-redirect-from', '~> 0.16.0'
diff --git a/Gemfile.lock b/Gemfile.lock
index 88f829a051d6b2f4ce52205e8d22950d58912bde..0858f93b2a93062d0414ec80e007fd189609e587 100644
--- a/Gemfile.lock
+++ b/Gemfile.lock
@@ -24,21 +24,21 @@ GEM
     http_parser.rb (0.6.0)
     i18n (1.8.5)
       concurrent-ruby (~> 1.0)
-    jekyll (4.1.1)
+    jekyll (4.2.0)
       addressable (~> 2.4)
       colorator (~> 1.0)
       em-websocket (~> 0.5)
       i18n (~> 1.0)
       jekyll-sass-converter (~> 2.0)
       jekyll-watch (~> 2.0)
-      kramdown (~> 2.1)
+      kramdown (~> 2.3)
       kramdown-parser-gfm (~> 1.0)
       liquid (~> 4.0)
       mercenary (~> 0.4.0)
       pathutil (~> 0.9)
       rouge (~> 3.0)
       safe_yaml (~> 1.0)
-      terminal-table (~> 1.8)
+      terminal-table (~> 2.0)
     jekyll-feed (0.15.1)
       jekyll (>= 3.7, < 5.0)
     jekyll-paginate (1.1.0)
@@ -55,7 +55,7 @@ GEM
     kramdown-parser-gfm (1.1.0)
       kramdown (~> 2.0)
     liquid (4.0.3)
-    listen (3.2.1)
+    listen (3.3.3)
       rb-fsevent (~> 0.10, >= 0.10.3)
       rb-inotify (~> 0.9, >= 0.9.10)
     mercenary (0.4.0)
@@ -77,7 +77,7 @@ GEM
     safe_yaml (1.0.5)
     sassc (2.4.0)
       ffi (~> 1.9)
-    terminal-table (1.8.0)
+    terminal-table (2.0.0)
       unicode-display_width (~> 1.1, >= 1.1.1)
     typhoeus (1.4.0)
       ethon (>= 0.9.0)
@@ -90,7 +90,7 @@ PLATFORMS
 
 DEPENDENCIES
   html-proofer (~> 3.17.4)
-  jekyll (~> 4.1.1)
+  jekyll (~> 4.2.0)
   jekyll-feed (~> 0.15.1)
   jekyll-paginate (~> 1.1.0)
   jekyll-redirect-from (~> 0.16.0)
diff --git a/_roadmap/backbone/2020-08-01.md b/_roadmap/backbone/2020-08-01-aai.md
similarity index 100%
rename from _roadmap/backbone/2020-08-01.md
rename to _roadmap/backbone/2020-08-01-aai.md
diff --git a/_roadmap/backbone/2020-09-01.md b/_roadmap/backbone/2020-09-01-agreement.md
similarity index 100%
rename from _roadmap/backbone/2020-09-01.md
rename to _roadmap/backbone/2020-09-01-agreement.md
diff --git a/_roadmap/backbone/2021-01-01.md b/_roadmap/backbone/2021-01-01-backbone.md
similarity index 100%
rename from _roadmap/backbone/2021-01-01.md
rename to _roadmap/backbone/2021-01-01-backbone.md
diff --git a/_roadmap/cloud/2020-05-01.md b/_roadmap/cloud/2020-05-01-service-selection.md
similarity index 100%
rename from _roadmap/cloud/2020-05-01.md
rename to _roadmap/cloud/2020-05-01-service-selection.md
diff --git a/_roadmap/cloud/2020-10-01.md b/_roadmap/cloud/2020-10-01-announce-portfolio.md
similarity index 100%
rename from _roadmap/cloud/2020-10-01.md
rename to _roadmap/cloud/2020-10-01-announce-portfolio.md
diff --git a/_roadmap/cloud/2020-10-15.md b/_roadmap/cloud/2020-10-15-integration-kickoff.md
similarity index 100%
rename from _roadmap/cloud/2020-10-15.md
rename to _roadmap/cloud/2020-10-15-integration-kickoff.md
diff --git a/_roadmap/cloud/2021-04-01.md b/_roadmap/cloud/2021-04-01-service-evaluation.md
similarity index 100%
rename from _roadmap/cloud/2021-04-01.md
rename to _roadmap/cloud/2021-04-01-service-evaluation.md
diff --git a/_roadmap/cloud/2021-12-01.md b/_roadmap/cloud/2021-12-01-process-manual.md
similarity index 100%
rename from _roadmap/cloud/2021-12-01.md
rename to _roadmap/cloud/2021-12-01-process-manual.md
diff --git a/_roadmap/cloud/2022-01-01.md b/_roadmap/cloud/2022-01-01-review-cloud-portfolio.md
similarity index 100%
rename from _roadmap/cloud/2022-01-01.md
rename to _roadmap/cloud/2022-01-01-review-cloud-portfolio.md
diff --git a/_roadmap/overall/2020-09-01.md b/_roadmap/overall/2020-09-01-helpdesk.md
similarity index 100%
rename from _roadmap/overall/2020-09-01.md
rename to _roadmap/overall/2020-09-01-helpdesk.md