diff --git a/src/Microsoft.DotNet.Configurer/NoOpFileSentinel.cs b/src/Microsoft.DotNet.Configurer/NoOpFileSentinel.cs
index e77097011..80e3d0831 100644
--- a/src/Microsoft.DotNet.Configurer/NoOpFileSentinel.cs
+++ b/src/Microsoft.DotNet.Configurer/NoOpFileSentinel.cs
@@ -7,9 +7,16 @@ namespace Microsoft.DotNet.Configurer
 {
     public class NoOpFileSentinel : IFileSentinel
     {
+        private bool _exists;
+
+        public NoOpFileSentinel(bool exists)
+        {
+            _exists = exists;
+        }
+
         public bool Exists()
         {
-            return true;
+            return _exists;
         }
 
         public void Create()
diff --git a/src/dotnet/Program.cs b/src/dotnet/Program.cs
index 6ae1409ce..ce08bcb56 100644
--- a/src/dotnet/Program.cs
+++ b/src/dotnet/Program.cs
@@ -147,7 +147,7 @@ namespace Microsoft.DotNet.Cli
                         {
                             aspNetCertificateSentinel = new NoOpAspNetCertificateSentinel();
                             firstTimeUseNoticeSentinel = new NoOpFirstTimeUseNoticeSentinel();
-                            toolPathSentinel = new NoOpFileSentinel();
+                            toolPathSentinel = new NoOpFileSentinel(exists: false);
                             hasSuperUserAccess = true;
                         }
 
diff --git a/test/dotnet.Tests/GivenThatTheUserIsRunningDotNetForTheFirstTime.cs b/test/dotnet.Tests/GivenThatTheUserIsRunningDotNetForTheFirstTime.cs
index bccc3c053..b554d528e 100644
--- a/test/dotnet.Tests/GivenThatTheUserIsRunningDotNetForTheFirstTime.cs
+++ b/test/dotnet.Tests/GivenThatTheUserIsRunningDotNetForTheFirstTime.cs
@@ -6,6 +6,7 @@ using System.IO;
 using System.Collections.Generic;
 using Microsoft.DotNet.Cli.Utils;
 using Microsoft.DotNet.Cli;
+using Microsoft.DotNet.Configurer;
 using Microsoft.DotNet.TestFramework;
 using Microsoft.DotNet.Tools.Test.Utilities;
 using Xunit;
@@ -193,6 +194,49 @@ namespace Microsoft.DotNet.Tests
                 .ContainVisuallySameFragment(Configurer.LocalizableStrings.AspNetCertificateInstalled);
         }
 
+        [LinuxOnlyFact]
+        public void ItCreatesTheProfileFileOnLinuxWhenInvokedFromNativeInstaller()
+        {
+            var emptyHome = Path.Combine(_testDirectory, "empty_home");
+            var profiled = Path.Combine(_testDirectory, "profile.d");
+
+            var command = new DotnetCommand().WithWorkingDirectory(_testDirectory);
+            command.Environment["HOME"] = emptyHome;
+            command.Environment["USERPROFILE"] = emptyHome;
+            command.Environment["APPDATA"] = emptyHome;
+            command.Environment["DOTNET_CLI_TEST_FALLBACKFOLDER"] = _nugetFallbackFolder.FullName;
+            command.Environment["DOTNET_SKIP_FIRST_TIME_EXPERIENCE"] = "";
+            command.Environment["DOTNET_CLI_TEST_LINUX_PROFILED_PATH"] = profiled;
+            command.Environment["DOTNET_DISABLE_MULTICOREJIT"] = "true";
+            command.Environment["SkipInvalidConfigurations"] = "true";
+            command.ExecuteWithCapturedOutput("internal-reportinstallsuccess test").Should().Pass();
+
+            File.Exists(profiled).Should().BeTrue();
+            File.ReadAllText(profiled).Should().Be(
+                $"export PATH=\"$PATH:{new CliFolderPathCalculator().ToolsShimPathInUnix.PathWithDollar}\"");
+        }
+
+        [MacOsOnlyFact]
+        public void ItCreatesThePathDFileOnMacOSWhenInvokedFromNativeInstaller()
+        {
+            var emptyHome = Path.Combine(_testDirectory, "empty_home");
+            var pathsd = Path.Combine(_testDirectory, "paths.d");
+
+            var command = new DotnetCommand().WithWorkingDirectory(_testDirectory);
+            command.Environment["HOME"] = emptyHome;
+            command.Environment["USERPROFILE"] = emptyHome;
+            command.Environment["APPDATA"] = emptyHome;
+            command.Environment["DOTNET_CLI_TEST_FALLBACKFOLDER"] = _nugetFallbackFolder.FullName;
+            command.Environment["DOTNET_SKIP_FIRST_TIME_EXPERIENCE"] = "";
+            command.Environment["DOTNET_CLI_TEST_OSX_PATHSD_PATH"] = pathsd;
+            command.Environment["DOTNET_DISABLE_MULTICOREJIT"] = "true";
+            command.Environment["SkipInvalidConfigurations"] = "true";
+            command.ExecuteWithCapturedOutput("internal-reportinstallsuccess test").Should().Pass();
+
+            File.Exists(pathsd).Should().BeTrue();
+            File.ReadAllText(pathsd).Should().Be(new CliFolderPathCalculator().ToolsShimPathInUnix.PathWithTilde);
+        }
+
         [Fact]
         public void ItRestoresTheNuGetPackagesToTheNuGetCacheFolder()
         {