diff --git a/src/Shared/CertificateGeneration/CertificateManager.cs b/src/Shared/CertificateGeneration/CertificateManager.cs
index 96e5630c43f1..491eb5adb974 100644
--- a/src/Shared/CertificateGeneration/CertificateManager.cs
+++ b/src/Shared/CertificateGeneration/CertificateManager.cs
@@ -328,6 +328,7 @@ public EnsureCertificateResult EnsureAspNetCoreHttpsDevelopmentCertificate(
                 var exportDir = Path.GetDirectoryName(path);
                 if (!string.IsNullOrEmpty(exportDir) && !Directory.Exists(exportDir))
                 {
+                    result = EnsureCertificateResult.ErrorExportingTheCertificateToNonExistentDirectory;
                     throw new InvalidOperationException($"The directory '{exportDir}' does not exist.  Choose permissions carefully when creating it.");
                 }
 
diff --git a/src/Shared/CertificateGeneration/EnsureCertificateResult.cs b/src/Shared/CertificateGeneration/EnsureCertificateResult.cs
index cb6b7e145428..5c28eaca3063 100644
--- a/src/Shared/CertificateGeneration/EnsureCertificateResult.cs
+++ b/src/Shared/CertificateGeneration/EnsureCertificateResult.cs
@@ -10,6 +10,7 @@ internal enum EnsureCertificateResult
     ErrorCreatingTheCertificate,
     ErrorSavingTheCertificateIntoTheCurrentUserPersonalStore,
     ErrorExportingTheCertificate,
+    ErrorExportingTheCertificateToNonExistentDirectory,
     FailedToTrustTheCertificate,
     PartiallyFailedToTrustTheCertificate,
     UserCancelledTrustStep,
diff --git a/src/Tools/FirstRunCertGenerator/test/CertificateManagerTests.cs b/src/Tools/FirstRunCertGenerator/test/CertificateManagerTests.cs
index 09a32825e50e..bcc2d6ef05b5 100644
--- a/src/Tools/FirstRunCertGenerator/test/CertificateManagerTests.cs
+++ b/src/Tools/FirstRunCertGenerator/test/CertificateManagerTests.cs
@@ -373,7 +373,7 @@ public void EnsureCreateHttpsCertificate_CannotExportToNonExistentDirectory()
             .EnsureAspNetCoreHttpsDevelopmentCertificate(now, now.AddYears(1), Path.Combine("NoSuchDirectory", CertificateName));
 
         // Assert
-        Assert.Equal(EnsureCertificateResult.ErrorExportingTheCertificate, result);
+        Assert.Equal(EnsureCertificateResult.ErrorExportingTheCertificateToNonExistentDirectory, result);
     }
 
     [Fact]
diff --git a/src/Tools/dotnet-dev-certs/src/Program.cs b/src/Tools/dotnet-dev-certs/src/Program.cs
index 9f5407d9d3e4..9b195dbcd9fa 100644
--- a/src/Tools/dotnet-dev-certs/src/Program.cs
+++ b/src/Tools/dotnet-dev-certs/src/Program.cs
@@ -425,6 +425,10 @@ private static int EnsureHttpsCertificate(CommandOption exportPath, CommandOptio
             case EnsureCertificateResult.ErrorExportingTheCertificate:
                 reporter.Warn("There was an error exporting the HTTPS developer certificate to a file.");
                 return ErrorExportingTheCertificate;
+            case EnsureCertificateResult.ErrorExportingTheCertificateToNonExistentDirectory:
+                // A distinct warning is useful, but a distinct error code is probably not.
+                reporter.Warn("There was an error exporting the HTTPS developer certificate to a file. Please create the target directory before exporting. Choose permissions carefully when creating it.");
+                return ErrorExportingTheCertificate;
             case EnsureCertificateResult.PartiallyFailedToTrustTheCertificate:
                 // A distinct warning is useful, but a distinct error code is probably not.
                 reporter.Warn("There was an error trusting the HTTPS developer certificate. It will be trusted by some clients but not by others.");