diff --git a/azure-pipelines.yml b/azure-pipelines.yml
index f788ca8e8..ba06b02a9 100644
--- a/azure-pipelines.yml
+++ b/azure-pipelines.yml
@@ -33,10 +33,10 @@ stages:
         matrix:
           Linux:
             osName: 'Linux'
-            imageName: 'ubuntu-16.04'
+            imageName: 'ubuntu-18.04'
           Mac:
             osName: 'Mac'
-            imageName: 'macos-10.13'
+            imageName: 'macos-10.14'
           Windows:
             osName: 'Windows'
             imageName: 'windows-2019'
@@ -94,10 +94,10 @@ stages:
         matrix:
           Linux:
             osName: 'Linux'
-            imageName: 'ubuntu-16.04'
+            imageName: 'ubuntu-18.04'
           Mac:
             osName: 'Mac'
-            imageName: 'macos-10.13'
+            imageName: 'macos-10.14'
           Windows:
             osName: 'Windows'
             imageName: 'windows-2019'
@@ -162,7 +162,7 @@ stages:
     - job: Other_Packages
       displayName: Create Standard Packages
       pool:
-        vmImage: 'ubuntu-16.04'
+        vmImage: 'ubuntu-18.04'
       steps:
       - checkout: self
         fetchDepth: 1
@@ -278,7 +278,7 @@ stages:
           MacCore:
             osName: 'Mac'
             testName: 'MacCore'
-            imageName: 'macos-10.13'
+            imageName: 'macos-10.14'
           WindowsCore:
             osName: 'Windows'
             testName: 'WindowsCore'
@@ -286,7 +286,7 @@ stages:
           LinuxCore:
             osName: 'Linux'
             testName: 'LinuxCore'
-            imageName: 'ubuntu-16.04'
+            imageName: 'ubuntu-18.04'
             pattern: 'Lidarr.**.linux-core-x64.tar.gz'
 
       pool:
@@ -314,7 +314,7 @@ stages:
         displayName: Install fpcalc
         condition: and(succeeded(), eq(variables['osName'], 'Linux'))
       - bash: |
-          SYMLINK=5_18_1
+          SYMLINK=6_6_0
           MONOPREFIX=/Library/Frameworks/Mono.framework/Versions/$SYMLINK
           echo "##vso[task.setvariable variable=MONOPREFIX;]$MONOPREFIX"
           echo "##vso[task.setvariable variable=PKG_CONFIG_PATH;]$MONOPREFIX/lib/pkgconfig:$MONOPREFIX/share/pkgconfig:$PKG_CONFIG_PATH"
@@ -359,7 +359,7 @@ stages:
             containerImage: lidarr/testimages:mono-6.10
 
       pool:
-        vmImage: 'ubuntu-16.04'
+        vmImage: 'ubuntu-18.04'
       
       container: $[ variables['containerImage'] ]
 
@@ -405,7 +405,7 @@ stages:
           MacCore:
             osName: 'Mac'
             testName: 'MacCore'
-            imageName: 'macos-10.13'
+            imageName: 'macos-10.14'
             pattern: 'Lidarr.**.osx-core-x64.tar.gz'
           WindowsCore:
             osName: 'Windows'
@@ -415,7 +415,7 @@ stages:
           LinuxCore:
             osName: 'Linux'
             testName: 'LinuxCore'
-            imageName: 'ubuntu-16.04'
+            imageName: 'ubuntu-18.04'
             pattern: 'Lidarr.**.linux-core-x64.tar.gz'
 
       pool:
@@ -423,7 +423,7 @@ stages:
         
       steps:
       - bash: |
-          SYMLINK=5_18_1
+          SYMLINK=6_6_0
           MONOPREFIX=/Library/Frameworks/Mono.framework/Versions/$SYMLINK
           echo "##vso[task.setvariable variable=MONOPREFIX;]$MONOPREFIX"
           echo "##vso[task.setvariable variable=PKG_CONFIG_PATH;]$MONOPREFIX/lib/pkgconfig:$MONOPREFIX/share/pkgconfig:$PKG_CONFIG_PATH"
@@ -492,7 +492,7 @@ stages:
         pattern: 'Lidarr.**.linux.tar.gz'
 
       pool:
-        vmImage: 'ubuntu-16.04'
+        vmImage: 'ubuntu-18.04'
 
       container: $[ variables['containerImage'] ]
 
@@ -552,12 +552,12 @@ stages:
         matrix:
           Linux:
             osName: 'Linux'
-            imageName: 'ubuntu-16.04'
+            imageName: 'ubuntu-18.04'
             pattern: 'Lidarr.**.linux-core-x64.tar.gz'
             failBuild: true
           Mac:
             osName: 'Mac'
-            imageName: 'macos-10.13' # Fails due to firefox not being installed on image
+            imageName: 'macos-10.14' # Fails due to firefox not being installed on image
             pattern: 'Lidarr.**.osx-core-x64.tar.gz'
             failBuild: false
           Windows:
@@ -637,7 +637,7 @@ stages:
         matrix:
           Linux:
             osName: 'Linux'
-            imageName: 'ubuntu-16.04'
+            imageName: 'ubuntu-18.04'
           Windows:
             osName: 'Windows'
             imageName: 'windows-2019'