diff --git a/src/Microsoft.DotNet.Cli.Utils/PathUtility.cs b/src/Microsoft.DotNet.Cli.Utils/PathUtility.cs
index c2e9c36bb..e9fdcb99c 100644
--- a/src/Microsoft.DotNet.Cli.Utils/PathUtility.cs
+++ b/src/Microsoft.DotNet.Cli.Utils/PathUtility.cs
@@ -56,6 +56,20 @@ namespace Microsoft.DotNet.Tools.Common
             return path + trailingCharacter;
         }
 
+        public static string EnsureNoTrailingSlash(string path)
+        {
+            if (!string.IsNullOrEmpty(path))
+            {
+                char lastChar = path[path.Length - 1];
+                if (lastChar == Path.DirectorySeparatorChar || lastChar == '/')
+                {
+                    path = path.Substring(0, path.Length - 1);
+                }
+            }
+
+            return path;
+        }
+
         public static void EnsureParentDirectory(string filePath)
         {
             string directory = Path.GetDirectoryName(filePath);
diff --git a/src/Microsoft.DotNet.Compiler.Common/Executable.cs b/src/Microsoft.DotNet.Compiler.Common/Executable.cs
index 008e14c1a..b15e8d147 100644
--- a/src/Microsoft.DotNet.Compiler.Common/Executable.cs
+++ b/src/Microsoft.DotNet.Compiler.Common/Executable.cs
@@ -281,7 +281,8 @@ namespace Microsoft.DotNet.Cli.Compiler.Common
                 var additionalProbingPaths = new JArray();
                 foreach (var packageFolder in _context.LockFile.PackageFolders)
                 {
-                    additionalProbingPaths.Add(packageFolder.Path);
+                    // DotNetHost doesn't handle additional probing paths with a trailing slash
+                    additionalProbingPaths.Add(PathUtility.EnsureNoTrailingSlash(packageFolder.Path));
                 }
 
                 runtimeOptions.Add("additionalProbingPaths", additionalProbingPaths);
diff --git a/src/Microsoft.DotNet.Core.Build.Tasks/GenerateRuntimeConfigurationFiles.cs b/src/Microsoft.DotNet.Core.Build.Tasks/GenerateRuntimeConfigurationFiles.cs
index c53a51363..41dc7e220 100644
--- a/src/Microsoft.DotNet.Core.Build.Tasks/GenerateRuntimeConfigurationFiles.cs
+++ b/src/Microsoft.DotNet.Core.Build.Tasks/GenerateRuntimeConfigurationFiles.cs
@@ -8,6 +8,7 @@ using System.Linq;
 using Microsoft.Build.Framework;
 using Microsoft.Build.Utilities;
 using Microsoft.DotNet.ProjectModel;
+using Microsoft.DotNet.Tools.Common;
 using Newtonsoft.Json;
 using Newtonsoft.Json.Linq;
 using Newtonsoft.Json.Serialization;
@@ -119,7 +120,8 @@ namespace Microsoft.DotNet.Cli.Tasks
                     runtimeOptions.AdditionalProbingPaths = new List<string>();
                 }
 
-                runtimeOptions.AdditionalProbingPaths.Add(packageFolder.Path);
+                // DotNetHost doesn't handle additional probing paths with a trailing slash
+                runtimeOptions.AdditionalProbingPaths.Add(PathUtility.EnsureNoTrailingSlash(packageFolder.Path));
             }
         }
 
diff --git a/src/dotnet/commands/dotnet-run/RunCommand.cs b/src/dotnet/commands/dotnet-run/RunCommand.cs
index 449192e3a..618f8074f 100644
--- a/src/dotnet/commands/dotnet-run/RunCommand.cs
+++ b/src/dotnet/commands/dotnet-run/RunCommand.cs
@@ -9,6 +9,7 @@ using System.Runtime.InteropServices;
 using Microsoft.DotNet.Cli.Utils;
 using Microsoft.DotNet.InternalAbstractions;
 using Microsoft.DotNet.ProjectModel;
+using Microsoft.DotNet.Tools.Common;
 using NuGet.Frameworks;
 
 namespace Microsoft.DotNet.Tools.Run
@@ -152,7 +153,8 @@ namespace Microsoft.DotNet.Tools.Run
 
                 foreach (var packageFolder in _context.LockFile.PackageFolders)
                 {
-                    hostArgs.Insert(0, packageFolder.Path);
+                    // DotNetHost doesn't handle additional probing paths with a trailing slash
+                    hostArgs.Insert(0, PathUtility.EnsureNoTrailingSlash(packageFolder.Path));
                     hostArgs.Insert(0, probingPathArg);
                 }
             }