diff --git a/dotnet/src/Functions/Functions.OpenApi/Model/RestApiOperation.cs b/dotnet/src/Functions/Functions.OpenApi/Model/RestApiOperation.cs
index 5bfa5a8a1ff2..4f4cd2a48948 100644
--- a/dotnet/src/Functions/Functions.OpenApi/Model/RestApiOperation.cs
+++ b/dotnet/src/Functions/Functions.OpenApi/Model/RestApiOperation.cs
@@ -412,19 +412,39 @@ value is string { } strValue &&
     };
 
     /// <summary>
-    /// Validates that the path does not contain dot-segments (. or ..) that could enable path traversal.
+    /// Validates that the path does not contain dot-segments (. or ..) that could enable path traversal,
+    /// including percent-encoded forms (e.g. "%2e%2e") that <see cref="Uri"/> canonicalizes at request time.
     /// ".." navigates up one path segment, enabling traversal to unintended endpoints.
     /// "." refers to the current directory — harmless but unexpected, so rejected to prevent misuse.
     /// </summary>
     /// <param name="path">The path to validate.</param>
     private static void ValidatePathSegments(string path)
     {
-        var segments = path.Split('/');
-        for (int i = 0; i < segments.Length; i++)
+        // Split on the structural path separator first.
+        foreach (var rawSegment in path.Split('/'))
         {
-            if (segments[i] == "." || segments[i] == "..")
+            // Decode percent-encoding until stable to catch encoded ("%2e") and
+            // double-encoded ("%252e") dot-segments before URI canonicalization.
+            var decoded = rawSegment;
+            for (int i = 0; i < 5; i++)
             {
-                throw new KernelException($"Path '{path}' contains a dot-segment, which could lead to path traversal.");
+                var unescaped = Uri.UnescapeDataString(decoded);
+                if (string.Equals(unescaped, decoded, StringComparison.Ordinal))
+                {
+                    break;
+                }
+
+                decoded = unescaped;
+            }
+
+            // A decoded segment may itself contain encoded separators ("%2f"/"%5c"),
+            // so re-split on both '/' and '\' and reject any resulting dot-segment.
+            foreach (var segment in decoded.Split('/', '\\'))
+            {
+                if (segment == "." || segment == "..")
+                {
+                    throw new KernelException($"Path '{path}' contains a dot-segment, which could lead to path traversal.");
+                }
             }
         }
     }
diff --git a/dotnet/src/Functions/Functions.UnitTests/OpenApi/RestApiOperationTests.cs b/dotnet/src/Functions/Functions.UnitTests/OpenApi/RestApiOperationTests.cs
index 9b17ae442731..6273c80d494e 100644
--- a/dotnet/src/Functions/Functions.UnitTests/OpenApi/RestApiOperationTests.cs
+++ b/dotnet/src/Functions/Functions.UnitTests/OpenApi/RestApiOperationTests.cs
@@ -1467,6 +1467,92 @@ public void ItShouldAllowDotsInNonSegmentPathParameterValues()
         Assert.Equal("https://example.com/api/files/report.v2.txt", url.OriginalString);
     }
 
+    [Theory]
+    [InlineData("/resources/%2e%2e/admin")]
+    [InlineData("/resources/%2E%2E/admin")]
+    [InlineData("/resources/%2e./admin")]
+    [InlineData("/resources/.%2e/admin")]
+    [InlineData("/resources/%2e%2e%2fadmin")]
+    [InlineData("/resources/%252e%252e/admin")]
+    [InlineData("/resources/%2e/admin")]
+    public void ItShouldRejectEncodedDotSegmentInPathTemplate(string path)
+    {
+        // Arrange — operation path template contains an encoded dot-segment that
+        // System.Uri would canonicalize into a path-traversal at request time.
+        var sut = new RestApiOperation(
+            id: "fake_id",
+            servers: [new RestApiServer("https://example.com/api")],
+            path: path,
+            method: HttpMethod.Get,
+            description: "fake_description",
+            parameters: [],
+            responses: new Dictionary<string, RestApiExpectedResponse>(),
+            securityRequirements: []
+        );
+
+        var arguments = new Dictionary<string, object?>();
+
+        // Act & Assert — encoded dot-segments must be rejected before URL is built
+        var ex = Assert.Throws<KernelException>(() => sut.BuildOperationUrl(arguments));
+        Assert.Contains("dot-segment", ex.Message);
+    }
+
+    [Fact]
+    public void ItShouldRejectEncodedDotSegmentInPathParameter()
+    {
+        // Arrange — path parameter value is an encoded ".." (%2e%2e)
+        var parameters = new List<RestApiParameter> {
+            new(
+                name: "id",
+                type: "string",
+                isRequired: true,
+                expand: false,
+                location: RestApiParameterLocation.Path,
+                style: RestApiParameterStyle.Simple)
+        };
+
+        var sut = new RestApiOperation(
+            id: "fake_id",
+            servers: [new RestApiServer("https://example.com/api")],
+            path: "/resources/{id}/details",
+            method: HttpMethod.Get,
+            description: "fake_description",
+            parameters: parameters,
+            responses: new Dictionary<string, RestApiExpectedResponse>(),
+            securityRequirements: []
+        );
+
+        var arguments = new Dictionary<string, object?> { { "id", "%2e%2e" } };
+
+        // Act & Assert — encoded dot-segments in parameter values must be rejected
+        var ex = Assert.Throws<KernelException>(() => sut.BuildOperationUrl(arguments));
+        Assert.Contains("dot-segment", ex.Message);
+    }
+
+    [Fact]
+    public void ItShouldAllowEncodedNonDotSegmentCharactersInPathTemplate()
+    {
+        // Arrange — path contains encoded characters that are NOT dot-segments
+        var sut = new RestApiOperation(
+            id: "fake_id",
+            servers: [new RestApiServer("https://example.com/api")],
+            path: "/resources/a%20b/details",
+            method: HttpMethod.Get,
+            description: "fake_description",
+            parameters: [],
+            responses: new Dictionary<string, RestApiExpectedResponse>(),
+            securityRequirements: []
+        );
+
+        var arguments = new Dictionary<string, object?>();
+
+        // Act
+        var url = sut.BuildOperationUrl(arguments);
+
+        // Assert — legitimate encoded characters must not be rejected
+        Assert.Equal("https://example.com/api/resources/a%20b/details", url.OriginalString);
+    }
+
     [Fact]
     public void ItShouldEncodeServerVariableValuesLookedUpByArgumentName()
     {
diff --git a/python/semantic_kernel/connectors/openapi_plugin/models/rest_api_operation.py b/python/semantic_kernel/connectors/openapi_plugin/models/rest_api_operation.py
index 570a4352892c..52e1c8aac59f 100644
--- a/python/semantic_kernel/connectors/openapi_plugin/models/rest_api_operation.py
+++ b/python/semantic_kernel/connectors/openapi_plugin/models/rest_api_operation.py
@@ -2,7 +2,7 @@
 
 import re
 from typing import Any, Final
-from urllib.parse import ParseResult, ParseResultBytes, quote, urlencode, urljoin, urlparse, urlunparse
+from urllib.parse import ParseResult, ParseResultBytes, quote, unquote, urlencode, urljoin, urlparse, urlunparse
 
 from semantic_kernel.connectors.openapi_plugin.models.rest_api_expected_response import (
     RestApiExpectedResponse,
@@ -289,8 +289,31 @@ def build_path(self, path_template: str, arguments: dict[str, Any]) -> str:
                     )
                 continue
             path_template = path_template.replace(f"{{{parameter.name}}}", quote(str(argument), safe=""))
+        self._validate_path_segments(path_template)
         return path_template
 
+    @staticmethod
+    def _validate_path_segments(path: str) -> None:
+        """Reject dot-segments (. or ..), including percent-encoded forms, that enable path traversal.
+
+        The operation is selected using the raw path but the request URL is built from a canonicalized
+        path, so encoded dot-segments such as "%2e%2e" must be rejected before the URL is constructed.
+        """
+        for segment in path.split("/"):
+            decoded = segment
+            for _ in range(5):
+                unescaped = unquote(decoded)
+                if unescaped == decoded:
+                    break
+                decoded = unescaped
+            # A decoded segment may contain encoded separators ("%2f"/"%5c"), so re-split on
+            # both "/" and "\" and reject any resulting dot-segment.
+            for part in decoded.replace("\\", "/").split("/"):
+                if part in (".", ".."):
+                    raise FunctionExecutionException(
+                        f"Path '{path}' contains a dot-segment, which could lead to path traversal."
+                    )
+
     def build_query_string(self, arguments: dict[str, Any]) -> str:
         """Build the query string for the operation."""
         segments = []
diff --git a/python/tests/unit/connectors/openapi_plugin/test_sk_openapi.py b/python/tests/unit/connectors/openapi_plugin/test_sk_openapi.py
index 2dd2488fc506..c59be28e9c55 100644
--- a/python/tests/unit/connectors/openapi_plugin/test_sk_openapi.py
+++ b/python/tests/unit/connectors/openapi_plugin/test_sk_openapi.py
@@ -435,9 +435,9 @@ def test_build_path_prevents_path_traversal():
         id="test", method="GET", servers=["https://example.com/"], path="/resource/{id}", params=parameters
     )
     arguments = {"id": "../../admin"}
-    result = operation.build_path(operation.path, arguments)
-    # The slashes must be encoded so ../../admin becomes a single path segment, not a traversal
-    assert result == "/resource/..%2F..%2Fadmin"
+    # Encoded separators that decode into dot-segments must be rejected, not silently encoded
+    with pytest.raises(FunctionExecutionException, match="dot-segment"):
+        operation.build_path(operation.path, arguments)
 
 
 def test_build_path_double_encodes_pre_encoded_values():
@@ -462,6 +462,40 @@ def test_build_path_encodes_unicode_characters():
     assert result == "/resource/caf%C3%A9%20r%C3%A9sum%C3%A9"
 
 
+@pytest.mark.parametrize(
+    "path",
+    [
+        "/resources/../admin",
+        "/resources/./admin",
+        "/resources/%2e%2e/admin",
+        "/resources/%2E%2E/admin",
+        "/resources/%2e/admin",
+        "/resources/%2e%2e%2fadmin",
+        "/resources/%252e%252e/admin",
+    ],
+)
+def test_build_path_rejects_dot_segment_in_template(path):
+    operation = RestApiOperation(id="test", method="GET", servers=["https://example.com/"], path=path, params=[])
+    with pytest.raises(FunctionExecutionException, match="dot-segment"):
+        operation.build_path(operation.path, {})
+
+
+def test_build_path_rejects_dot_segment_via_parameter():
+    parameters = [RestApiParameter(name="id", type="string", location=RestApiParameterLocation.PATH, is_required=True)]
+    operation = RestApiOperation(
+        id="test", method="GET", servers=["https://example.com/"], path="/resource/{id}/details", params=parameters
+    )
+    with pytest.raises(FunctionExecutionException, match="dot-segment"):
+        operation.build_path(operation.path, {"id": ".."})
+
+
+def test_build_path_allows_encoded_non_dot_segment_characters():
+    operation = RestApiOperation(
+        id="test", method="GET", servers=["https://example.com/"], path="/resources/a%20b/details", params=[]
+    )
+    assert operation.build_path(operation.path, {}) == "/resources/a%20b/details"
+
+
 def test_build_query_string_with_required_parameter():
     parameters = [
         RestApiParameter(name="query", type="string", location=RestApiParameterLocation.QUERY, is_required=True)