diff --git a/src/Microsoft.PowerShell.Commands.Management/commands/management/ResolvePathCommand.cs b/src/Microsoft.PowerShell.Commands.Management/commands/management/ResolvePathCommand.cs
index 140c4c3e1..6f260a89f 100644
--- a/src/Microsoft.PowerShell.Commands.Management/commands/management/ResolvePathCommand.cs
+++ b/src/Microsoft.PowerShell.Commands.Management/commands/management/ResolvePathCommand.cs
@@ -105,13 +105,26 @@ namespace Microsoft.PowerShell.Commands
                     {
                         foreach (PathInfo currentPath in result)
                         {
+                            // When result path and base path is on different PSDrive
+                            // (../)*path should not go beyond the root of base path
+                            if (currentPath.Drive != SessionState.Path.CurrentLocation.Drive &&
+                                SessionState.Path.CurrentLocation.Drive != null &&
+                                !currentPath.ProviderPath.StartsWith(
+                                    SessionState.Path.CurrentLocation.Drive.Root, StringComparison.OrdinalIgnoreCase))
+                            {
+                                WriteObject(currentPath.Path, enumerateCollection: false);
+                                continue;
+                            }
                             string adjustedPath = SessionState.Path.NormalizeRelativePath(currentPath.Path,
                                 SessionState.Path.CurrentLocation.ProviderPath);
-                            if (!adjustedPath.StartsWith(".", StringComparison.OrdinalIgnoreCase))
+                            // Do not insert './' if result path is not relative
+                            if (!adjustedPath.StartsWith(
+                                    currentPath.Drive?.Root ?? currentPath.Path, StringComparison.OrdinalIgnoreCase) &&
+                                !adjustedPath.StartsWith(".", StringComparison.OrdinalIgnoreCase))
                             {
                                 adjustedPath = SessionState.Path.Combine(".", adjustedPath);
                             }
-                            WriteObject(adjustedPath, false);
+                            WriteObject(adjustedPath, enumerateCollection: false);
                         }
                     }
                 }
@@ -150,7 +163,7 @@ namespace Microsoft.PowerShell.Commands
 
                 if (!_relative)
                 {
-                    WriteObject(result, true);
+                    WriteObject(result, enumerateCollection: true);
                 }
             }
         } // ProcessRecord
diff --git a/test/powershell/Modules/Microsoft.PowerShell.Management/Resolve-Path.Tests.ps1 b/test/powershell/Modules/Microsoft.PowerShell.Management/Resolve-Path.Tests.ps1
index e5c5533a2..9494c1ed9 100644
--- a/test/powershell/Modules/Microsoft.PowerShell.Management/Resolve-Path.Tests.ps1
+++ b/test/powershell/Modules/Microsoft.PowerShell.Management/Resolve-Path.Tests.ps1
@@ -1,6 +1,25 @@
 # Copyright (c) Microsoft Corporation. All rights reserved.
 # Licensed under the MIT License.
 Describe "Resolve-Path returns proper path" -Tag "CI" {
+    BeforeAll {
+        $driveName = "RvpaTest"
+        $root = Join-Path $TestDrive "fakeroot"
+        $file = Join-Path $root "file.txt"
+        $null = New-Item -Path $root -ItemType Directory -Force
+        $null = New-Item -Path $file -ItemType File -Force
+        $null = New-PSDrive -Name $driveName -PSProvider FileSystem -Root $root
+
+        $testRoot = Join-Path $TestDrive ""
+        $fakeRoot = Join-Path "$driveName`:" ""
+
+        $relCases = @(
+            @{ wd = $fakeRoot; target = $testRoot; expected = $testRoot }
+            @{ wd = $testRoot; target = Join-Path $fakeRoot "file.txt"; expected = Join-Path "." "fakeroot" "file.txt" }
+        )
+    }
+    AfterAll {
+        Remove-PSDrive -Name $driveName -Force
+    }
     It "Resolve-Path returns resolved paths" {
         Resolve-Path $TESTDRIVE | Should -BeExactly "$TESTDRIVE"
     }
@@ -19,4 +38,14 @@ Describe "Resolve-Path returns proper path" -Tag "CI" {
         $result = Resolve-Path -LiteralPath "TestDrive:\\\\\"
         ($result.Path.TrimEnd('/\')) | Should -BeExactly "TestDrive:"
     }
+    It "Resolve-Path -Relative '<target>' should return correct path on '<wd>'" -TestCases $relCases {
+        param($wd, $target, $expected)
+        try {
+            Push-Location -Path $wd
+            Resolve-Path -Path $target -Relative | Should -BeExactly $expected
+        }
+        finally {
+            Pop-Location
+        }
+    }
 }