diff --git a/.github/workflows/build.yaml b/.github/workflows/build.yaml
index f592b21..17f9601 100644
--- a/.github/workflows/build.yaml
+++ b/.github/workflows/build.yaml
@@ -38,6 +38,7 @@ jobs:
       options: --cap-add=SYS_PTRACE --security-opt seccomp=unconfined
     steps:
     - uses: actions/checkout@v2
+
     - run: |
         eval $(/home/linuxbrew/.linuxbrew/bin/brew shellenv)
         go get -u github.com/go-delve/delve/cmd/dlv
@@ -79,17 +80,26 @@ jobs:
         name: 'package-linux'
         path: 'package/linux-${{ github.run_id }}.tar.gz'
 
+    # - name: Start SSH session if failed
+    #   uses: luchihoratiu/debug-via-ssh@main
+    #   if: failure()
+    #   with:
+    #     NGROK_AUTH_TOKEN: ${{ secrets.NGROK_AUTH_TOKEN }}
+    #     SSH_PASS: ${{ secrets.SSH_PASS }}
+
   MacOS:
     runs-on: 'macos-10.15'
     steps:
     - uses: actions/checkout@v2
+
     - run: |
         brew update-reset
         brew doctor || true
-        for p in macvim tcl-tk llvm lua luajit love; do
-          brew install $p
-          brew outdated $p || brew upgrade $p
+        for p in python@3.8 tcl-tk llvm lua luajit love; do
+          brew install $p || brew outdated $p || brew upgrade $p
         done
+        brew install --cask macvim
+        brew link --overwrite python@3.8
       name: 'Install vim and deps'
 
     - run: go get -u github.com/go-delve/delve/cmd/dlv
@@ -128,6 +138,13 @@ jobs:
         name: 'package-macos'
         path: 'package/macos-${{ github.run_id }}.tar.gz'
 
+    # - name: Start SSH session if failed
+    #   uses: luchihoratiu/debug-via-ssh@main
+    #   if: failure()
+    #   with:
+    #     NGROK_AUTH_TOKEN: ${{ secrets.NGROK_AUTH_TOKEN }}
+    #     SSH_PASS: ${{ secrets.SSH_PASS }}
+
   PublishRelease:
     runs-on: 'ubuntu-16.04'
     needs:
diff --git a/python3/vimspector/variables.py b/python3/vimspector/variables.py
index 1d62c04..4028722 100644
--- a/python3/vimspector/variables.py
+++ b/python3/vimspector/variables.py
@@ -84,6 +84,12 @@ class WatchResult( Expandable ):
     self.result = result
 
 
+class WatchFailure( WatchResult ):
+  def __init__( self, reason ):
+    super().__init__( { 'result': reason } )
+    self.changed = True
+
+
 class Variable( Expandable ):
   """Holds one level of an expanded value tree. Also itself expandable."""
   def __init__( self, variable: dict ):
@@ -296,11 +302,14 @@ class VariablesView( object ):
 
   def EvaluateWatches( self ):
     for watch in self._watches:
-      self._connection.DoRequest( partial( self._UpdateWatchExpression,
-                                           watch ), {
-        'command': 'evaluate',
-        'arguments': watch.expression,
-      } )
+      self._connection.DoRequest(
+        partial( self._UpdateWatchExpression, watch ),
+        {
+          'command': 'evaluate',
+          'arguments': watch.expression,
+        },
+        failure_handler = lambda reason, msg, watch=watch:
+            self._WatchExpressionFailed( reason, watch ) )
 
   def _UpdateWatchExpression( self, watch: Watch, message: dict ):
     if watch.result is not None:
@@ -321,6 +330,14 @@ class VariablesView( object ):
 
     self._DrawWatches()
 
+  def _WatchExpressionFailed( self, reason: str, watch: Watch ):
+    if watch.result is not None:
+      # We already have a result for this watch. Wut ?
+      return
+
+    watch.result = WatchFailure( reason )
+    self._DrawWatches()
+
   def ExpandVariable( self ):
     if vim.current.buffer == self._vars.buf:
       view = self._vars
diff --git a/tests/variables.test.vim b/tests/variables.test.vim
index 155e1d9..9152875 100644
--- a/tests/variables.test.vim
+++ b/tests/variables.test.vim
@@ -557,3 +557,37 @@ function Test_EvaluatePromptConsole()
   call vimspector#test#setup#Reset()
   %bwipe!
 endfunction
+
+function! Test_EvaluateFailure()
+  call s:StartDebugging()
+
+  " Add a wtch
+  call vimspector#AddWatch( 'test' )
+  call WaitForAssert( {->
+        \   AssertMatchist(
+        \     [
+        \       'Watches: ----',
+        \       'Expression: test',
+        \       " *- Result: NameError: name 'test' is not defined",
+        \     ],
+        \     getbufline( winbufnr( g:vimspector_session_windows.watches ),
+        \                 1,
+        \                 '$' )
+        \   )
+        \ } )
+
+  VimspectorEval test
+  call assert_equal( bufnr( 'vimspector.Console' ),
+                   \ winbufnr( g:vimspector_session_windows.output ) )
+  call WaitForAssert( {->
+        \   assert_equal(
+        \     [
+        \       "NameError: name 'test' is not defined"
+        \     ],
+        \     getbufline( bufnr( 'vimspector.Console' ), '$', '$' )
+        \   )
+        \ } )
+
+  call vimspector#test#setup#Reset()
+  %bwipe!
+endfunction