diff --git a/build.psm1 b/build.psm1
index 81bf045cda..e4cf5d0d32 100644
--- a/build.psm1
+++ b/build.psm1
@@ -222,6 +222,7 @@ function Start-PSBuild {
             # This is allowed to fail since the user may have already restored
             Write-Warning ".NET Core links the incorrect OpenSSL, correcting NuGet package libraries..."
             find $env:HOME/.nuget -name System.Security.Cryptography.Native.dylib | xargs sudo install_name_tool -add_rpath /usr/local/opt/openssl/lib
+            find $env:HOME/.nuget -name System.Net.Http.Native.dylib | xargs sudo install_name_tool -change /usr/lib/libcurl.4.dylib /usr/local/opt/curl/lib/libcurl.4.dylib
         }
     }
 
@@ -820,13 +821,16 @@ function Start-PSBootstrap {
             precheck 'brew' "Bootstrap dependency 'brew' not found, must install Homebrew! See http://brew.sh/"
 
             # Build tools
-            $Deps += "curl", "cmake"
+            $Deps += "cmake"
 
             # .NET Core required runtime libraries
             $Deps += "openssl"
 
             # Install dependencies
             Start-NativeExecution { brew install $Deps }
+
+            # Install patched version of curl
+            Start-NativeExecution { brew install curl --with-openssl }
         }
 
         # Install [fpm](https://github.com/jordansissel/fpm) and [ronn](https://github.com/rtomayko/ronn)
diff --git a/docs/installation/linux.md b/docs/installation/linux.md
index 0a48a72495..4c6933e349 100644
--- a/docs/installation/linux.md
+++ b/docs/installation/linux.md
@@ -142,6 +142,7 @@ Also install [Homebrew's OpenSSL][openssl]:
 
 ```
 brew install openssl
+brew install curl --with-openssl
 ```
 
 [Homebrew][brew] is the missing package manager for macOS.
@@ -167,6 +168,7 @@ To patch .NET Core's cryptography libraries, we use `install_name_tool`:
 
 ```
 find ~/.nuget -name System.Security.Cryptography.Native.dylib | xargs sudo install_name_tool -add_rpath /usr/local/opt/openssl/lib
+find ~/.nuget -name System.Net.Http.Native.dylib | xargs sudo install_name_tool -change /usr/lib/libcurl.4.dylib /usr/local/opt/curl/lib/libcurl.4.dylib
 ```
 
 This updates .NET Core's library to look in Homebrew's OpenSSL installation location instead of the system library location.
diff --git a/tools/download.sh b/tools/download.sh
index 26f0c4bfd4..d0ba82e560 100755
--- a/tools/download.sh
+++ b/tools/download.sh
@@ -87,14 +87,22 @@ case "$OSTYPE" in
         esac
         ;;
     darwin*)
+        patched=0
         if hash brew 2>/dev/null; then
             if [[ ! -d $(brew --prefix openssl) ]]; then
                echo "Installing OpenSSL with brew..."
                if ! brew install openssl; then
                    echo "ERROR: OpenSSL failed to install! Crypto functions will not work..." >&2
                    # Don't abort because it is not fatal
+               elif ! brew install curl --with-openssl; then
+                   echo "ERROR: curl failed to build against OpenSSL; SSL functions will not work..." >&2
+                   # Still not fatal
+               else
+                   # OpenSSL installation succeeded; remember to patch System.Net.Http after PowerShell installation
+                   patched=1
                fi
             fi
+
         else
             echo "ERROR: brew not found! OpenSSL may not be available..." >&2
             # Don't abort because it is not fatal
@@ -102,6 +110,10 @@ case "$OSTYPE" in
 
         echo "Installing $package with sudo ..."
         sudo installer -pkg "./$package" -target /
+        if [[ $patched -eq 1 ]]; then
+            echo "Patching System.Net.Http for libcurl and OpenSSL..."
+            find /usr/local/microsoft/powershell -name System.Net.Http.Native.dylib | xargs sudo install_name_tool -change /usr/lib/libcurl.4.dylib /usr/local/opt/curl/lib/libcurl.4.dylib
+        fi
         ;;
 esac