diff --git a/plugins/hosts/windows/cap/smb.rb b/plugins/hosts/windows/cap/smb.rb
index d224e06a3..457807f9c 100644
--- a/plugins/hosts/windows/cap/smb.rb
+++ b/plugins/hosts/windows/cap/smb.rb
@@ -63,7 +63,9 @@ module VagrantPlugins
 
             # Check if this name is already in use
             if share_info = current_shares[data[:smb_id]]
-              if !hostpath.empty? && share_info["Path"].downcase != hostpath.downcase
+              exist_path = File.expand_path(share_info["Path"]).downcase
+              request_path = File.expand_path(hostpath).downcase
+              if !hostpath.empty? && exist_path != request_path
                 raise SyncedFolderSMB::Errors::SMBNameError,
                   path: hostpath,
                   existing_path: share_info["Path"],
diff --git a/test/unit/plugins/hosts/windows/cap/smb_test.rb b/test/unit/plugins/hosts/windows/cap/smb_test.rb
index 216be6397..c904bc205 100644
--- a/test/unit/plugins/hosts/windows/cap/smb_test.rb
+++ b/test/unit/plugins/hosts/windows/cap/smb_test.rb
@@ -110,6 +110,29 @@ Description : Not Vagrant Owned
       subject.smb_prepare(env, machine, folders, options)
     end
 
+    context "when share already exists" do
+      let(:shares){ {"ID1" => {"Path" => "/host/2"}} }
+      before do
+        allow(File).to receive(:expand_path).and_call_original
+        expect(subject).to receive(:existing_shares).and_return(shares)
+      end
+
+      it "should expand paths when comparing existing to requested" do
+        expect(File).to receive(:expand_path).at_least(2).with("/host/2").and_return("expanded_path")
+        subject.smb_prepare(env, machine, folders, options)
+      end
+
+      context "with different path" do
+        let(:shares){ {"ID1" => {"Path" => "/host/3"}} }
+
+        it "should raise an error" do
+          expect{
+            subject.smb_prepare(env, machine, folders, options)
+          }.to raise_error(VagrantPlugins::SyncedFolderSMB::Errors::SMBNameError)
+        end
+      end
+    end
+
     context "when no shared are defined" do
       after{ subject.smb_prepare(env, machine, {}, options) }