diff --git a/.travis.yml b/.travis.yml
index 0126c52d6e..1f8c14d26e 100644
--- a/.travis.yml
+++ b/.travis.yml
@@ -25,6 +25,10 @@ install:
       rvm install ruby-2.3.3;
       rvm --default use 2.3.3;
     fi
+  # Ensure that libcurl+openssl is used on macOS for greater feature support.
+  - if [[ "$TRAVIS_OS_NAME" == "osx" ]]; then
+      export DYLD_LIBRARY_PATH=/usr/local/opt/curl/lib:/usr/local/opt/openssl/lib:${DYLD_LIBRARY_PATH};
+    fi
   - pushd tools
   - ./install-powershell.sh
   - popd
diff --git a/CHANGELOG.md b/CHANGELOG.md
index 862bd30b3a..3e03903f90 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -5,6 +5,7 @@
 - Update the contribution guideline to note that updating the changelog is required. (#5586)
 - Remove Pester as a module include with the PowerShell Packages.
   In the future, you should be able to add it by running `Install-Module Pester`. (#5623, #5631)
+- Make Travis CI use `libcurl+openssl+gssapi` (#5629, @markekraus)
 
 ## v6.0.0-rc - 2017-11-16
 
diff --git a/build.psm1 b/build.psm1
index 7af1d0ee34..a5f4a1c540 100644
--- a/build.psm1
+++ b/build.psm1
@@ -1533,7 +1533,7 @@ function Start-PSBootstrap {
                 Start-NativeExecution { brew install $Deps } -IgnoreExitcode
 
                 # Install patched version of curl
-                Start-NativeExecution { brew install curl --with-openssl } -IgnoreExitcode
+                Start-NativeExecution { brew install curl --with-openssl --with-gssapi } -IgnoreExitcode
             }
 
             # Install [fpm](https://github.com/jordansissel/fpm) and [ronn](https://github.com/rtomayko/ronn)
diff --git a/test/powershell/Modules/Microsoft.PowerShell.Utility/WebCmdlets.Tests.ps1 b/test/powershell/Modules/Microsoft.PowerShell.Utility/WebCmdlets.Tests.ps1
index e9282b5245..bf77837d4f 100644
--- a/test/powershell/Modules/Microsoft.PowerShell.Utility/WebCmdlets.Tests.ps1
+++ b/test/powershell/Modules/Microsoft.PowerShell.Utility/WebCmdlets.Tests.ps1
@@ -1412,9 +1412,8 @@ Describe "Invoke-WebRequest tests" -Tags "Feature" {
             $testCases1 = @(
                 @{ Test = @{SslProtocol = 'Default'; ActualProtocol = 'Default'}; Pending = $false }
                 @{ Test = @{SslProtocol = 'Tls'; ActualProtocol = 'Tls'}; Pending = $false }
-                # these two currently fail on Travis CI macOS build
-                @{ Test = @{SslProtocol = 'Tls11'; ActualProtocol = 'Tls11'}; Pending = $IsMacOS }
-                @{ Test = @{SslProtocol = 'Tls12'; ActualProtocol = 'Tls12'}; Pending = $IsMacOS }
+                @{ Test = @{SslProtocol = 'Tls11'; ActualProtocol = 'Tls11'}; Pending = $false }
+                @{ Test = @{SslProtocol = 'Tls12'; ActualProtocol = 'Tls12'}; Pending = $false }
                 # macOS does not support multiple SslProtocols
                 @{ Test = @{SslProtocol = 'Tls, Tls11, Tls12'; ActualProtocol = 'Tls12'}; Pending = $IsMacOS }
                 @{ Test = @{SslProtocol = 'Tls11, Tls12'; ActualProtocol = 'Tls12'}; Pending = $IsMacOS }
@@ -1433,9 +1432,8 @@ Describe "Invoke-WebRequest tests" -Tags "Feature" {
                 @{ Test = @{IntendedProtocol = 'Tls';   ActualProtocol = 'Tls11'}; Pending = $false }
                 @{ Test = @{IntendedProtocol = 'Tls11'; ActualProtocol = 'Tls12'}; Pending = $false }
                 @{ Test = @{IntendedProtocol = 'Tls12'; ActualProtocol = 'Tls11'}; Pending = $false }
-                # these two currently fail on Travis CI macOS build
-                @{ Test = @{IntendedProtocol = 'Tls11'; ActualProtocol = 'Tls'}; Pending = $IsMacOS }
-                @{ Test = @{IntendedProtocol = 'Tls12'; ActualProtocol = 'Tls'}; Pending = $IsMacOS }
+                @{ Test = @{IntendedProtocol = 'Tls11'; ActualProtocol = 'Tls'}; Pending = $false }
+                @{ Test = @{IntendedProtocol = 'Tls12'; ActualProtocol = 'Tls'}; Pending = $false }
                 # macOS does not support multiple SslProtocols
                 @{ Test = @{IntendedProtocol = 'Tls11, Tls12';   ActualProtocol = 'Tls'}; Pending = $IsMacOS }
                 @{ Test = @{IntendedProtocol = 'Tls, Tls12';   ActualProtocol = 'Tls11'}; Pending = $IsMacOS }
@@ -2382,9 +2380,8 @@ Describe "Invoke-RestMethod tests" -Tags "Feature" {
             $testCases1 = @(
                 @{ Test = @{SslProtocol = 'Default'; ActualProtocol = 'Default'}; Pending = $false }
                 @{ Test = @{SslProtocol = 'Tls'; ActualProtocol = 'Tls'}; Pending = $false }
-                # these two currently fail on Travis CI macOS build
-                @{ Test = @{SslProtocol = 'Tls11'; ActualProtocol = 'Tls11'}; Pending = $IsMacOS }
-                @{ Test = @{SslProtocol = 'Tls12'; ActualProtocol = 'Tls12'}; Pending = $IsMacOS }
+                @{ Test = @{SslProtocol = 'Tls11'; ActualProtocol = 'Tls11'}; Pending = $false }
+                @{ Test = @{SslProtocol = 'Tls12'; ActualProtocol = 'Tls12'}; Pending = $false }
                 # macOS does not support multiple SslProtocols
                 @{ Test = @{SslProtocol = 'Tls, Tls11, Tls12'; ActualProtocol = 'Tls12'}; Pending = $IsMacOS }
                 @{ Test = @{SslProtocol = 'Tls11, Tls12'; ActualProtocol = 'Tls12'}; Pending = $IsMacOS }
@@ -2403,9 +2400,8 @@ Describe "Invoke-RestMethod tests" -Tags "Feature" {
                 @{ Test = @{IntendedProtocol = 'Tls';   ActualProtocol = 'Tls11'}; Pending = $false }
                 @{ Test = @{IntendedProtocol = 'Tls11'; ActualProtocol = 'Tls12'}; Pending = $false }
                 @{ Test = @{IntendedProtocol = 'Tls12'; ActualProtocol = 'Tls11'}; Pending = $false }
-                # these two currently fail on Travis CI macOS build
-                @{ Test = @{IntendedProtocol = 'Tls11'; ActualProtocol = 'Tls'}; Pending = $IsMacOS }
-                @{ Test = @{IntendedProtocol = 'Tls12'; ActualProtocol = 'Tls'}; Pending = $IsMacOS }
+                @{ Test = @{IntendedProtocol = 'Tls11'; ActualProtocol = 'Tls'}; Pending = $false }
+                @{ Test = @{IntendedProtocol = 'Tls12'; ActualProtocol = 'Tls'}; Pending = $false }
                 # macOS does not support multiple SslProtocols
                 @{ Test = @{IntendedProtocol = 'Tls11, Tls12';   ActualProtocol = 'Tls'}; Pending = $IsMacOS }
                 @{ Test = @{IntendedProtocol = 'Tls, Tls12';   ActualProtocol = 'Tls11'}; Pending = $IsMacOS }