diff --git a/docs/config.png b/docs/config.png
index 7e2bf4fa..d32bc8a5 100644
Binary files a/docs/config.png and b/docs/config.png differ
diff --git a/docs/config.puml b/docs/config.puml
index 8f0a4400..0a1d0b21 100644
--- a/docs/config.puml
+++ b/docs/config.puml
@@ -73,12 +73,14 @@ class "JwtConfiguration" as src.models.config.JwtConfiguration {
   username_claim : str
 }
 class "JwtRoleRule" as src.models.config.JwtRoleRule {
+  compiled_regex
   jsonpath : str
   negate : bool
   operator
   roles : list[str]
   value : Any
   check_jsonpath() -> Self
+  check_regex_pattern() -> Self
   check_roles() -> Self
 }
 class "LlamaStackConfiguration" as src.models.config.LlamaStackConfiguration {
diff --git a/docs/config.svg b/docs/config.svg
index 8ec02c99..97b3e8fe 100644
--- a/docs/config.svg
+++ b/docs/config.svg
@@ -1,5 +1,5 @@
 <?xml version="1.0"?>
-<svg xmlns="http://www.w3.org/2000/svg" xmlns:xlink="http://www.w3.org/1999/xlink" contentStyleType="text/css" height="920px" preserveAspectRatio="none" style="width:3020px;height:920px;background:#FFFFFF;" version="1.1" viewBox="0 0 3020 920" width="3020px" zoomAndPan="magnify">
+<svg xmlns="http://www.w3.org/2000/svg" xmlns:xlink="http://www.w3.org/1999/xlink" contentStyleType="text/css" height="920px" preserveAspectRatio="none" style="width:3058px;height:920px;background:#FFFFFF;" version="1.1" viewBox="0 0 3058 920" width="3058px" zoomAndPan="magnify">
   <defs/>
   <g>
     <!--class src.models.config.AccessRule-->
@@ -15,13 +15,13 @@
     </g>
     <!--class src.models.config.Action-->
     <g id="elem_src.models.config.Action">
-      <rect codeLine="6" fill="#F1F1F1" height="67.0679" id="src.models.config.Action" rx="2.5" ry="2.5" style="stroke:#181818;stroke-width:0.5;" width="73.4538" x="2836.15" y="45.14"/>
-      <ellipse cx="2851.15" cy="61.14" fill="#ADD1B2" rx="11" ry="11" style="stroke:#181818;stroke-width:1.0;"/>
-      <path d="M2851.2594,56.6712 Q2850.3375,56.6712 2849.6031,56.9837 Q2848.8844,57.2962 2848.3844,57.89 Q2847.8844,58.4681 2847.6031,59.3431 Q2847.3375,60.2181 2847.3375,61.3119 Q2847.3375,62.7494 2847.775,63.7962 Q2848.2281,64.8431 2849.0719,65.39 Q2849.9313,65.9369 2851.2438,65.9369 Q2852.025,65.9369 2852.7125,65.8119 Q2853.4156,65.6712 2854.4156,65.3587 L2854.4156,67.2337 Q2853.5563,67.5619 2852.7906,67.6869 Q2852.0406,67.8119 2851.025,67.8119 Q2849.1031,67.8119 2847.7906,67.015 Q2846.4938,66.2025 2845.8375,64.7337 Q2845.1813,63.2494 2845.1813,61.2806 Q2845.1813,59.8587 2845.5719,58.6869 Q2845.9781,57.4994 2846.7594,56.6244 Q2847.5406,55.7494 2848.6813,55.2806 Q2849.8219,54.7962 2851.2906,54.7962 Q2852.2438,54.7962 2853.1344,54.9994 Q2854.0406,55.1869 2854.9781,55.6556 L2854.15,57.4369 Q2853.3688,57.0619 2852.7125,56.8744 Q2852.0563,56.6712 2851.2594,56.6712 Z " fill="#000000"/>
-      <text fill="#000000" font-family="sans-serif" font-size="14" lengthAdjust="spacing" textLength="41.4538" x="2865.15" y="66.572">Action</text>
-      <line style="stroke:#181818;stroke-width:0.5;" x1="2837.15" x2="2908.6038" y1="77.14" y2="77.14"/>
-      <text fill="#000000" font-family="sans-serif" font-size="14" lengthAdjust="spacing" textLength="37.4919" x="2842.15" y="96.1059">name</text>
-      <line style="stroke:#181818;stroke-width:0.5;" x1="2837.15" x2="2908.6038" y1="104.2079" y2="104.2079"/>
+      <rect codeLine="6" fill="#F1F1F1" height="67.0679" id="src.models.config.Action" rx="2.5" ry="2.5" style="stroke:#181818;stroke-width:0.5;" width="73.4538" x="2862.15" y="45.14"/>
+      <ellipse cx="2877.15" cy="61.14" fill="#ADD1B2" rx="11" ry="11" style="stroke:#181818;stroke-width:1.0;"/>
+      <path d="M2877.2594,56.6712 Q2876.3375,56.6712 2875.6031,56.9837 Q2874.8844,57.2962 2874.3844,57.89 Q2873.8844,58.4681 2873.6031,59.3431 Q2873.3375,60.2181 2873.3375,61.3119 Q2873.3375,62.7494 2873.775,63.7962 Q2874.2281,64.8431 2875.0719,65.39 Q2875.9313,65.9369 2877.2438,65.9369 Q2878.025,65.9369 2878.7125,65.8119 Q2879.4156,65.6712 2880.4156,65.3587 L2880.4156,67.2337 Q2879.5563,67.5619 2878.7906,67.6869 Q2878.0406,67.8119 2877.025,67.8119 Q2875.1031,67.8119 2873.7906,67.015 Q2872.4938,66.2025 2871.8375,64.7337 Q2871.1813,63.2494 2871.1813,61.2806 Q2871.1813,59.8587 2871.5719,58.6869 Q2871.9781,57.4994 2872.7594,56.6244 Q2873.5406,55.7494 2874.6813,55.2806 Q2875.8219,54.7962 2877.2906,54.7962 Q2878.2438,54.7962 2879.1344,54.9994 Q2880.0406,55.1869 2880.9781,55.6556 L2880.15,57.4369 Q2879.3688,57.0619 2878.7125,56.8744 Q2878.0563,56.6712 2877.2594,56.6712 Z " fill="#000000"/>
+      <text fill="#000000" font-family="sans-serif" font-size="14" lengthAdjust="spacing" textLength="41.4538" x="2891.15" y="66.572">Action</text>
+      <line style="stroke:#181818;stroke-width:0.5;" x1="2863.15" x2="2934.6038" y1="77.14" y2="77.14"/>
+      <text fill="#000000" font-family="sans-serif" font-size="14" lengthAdjust="spacing" textLength="37.4919" x="2868.15" y="96.1059">name</text>
+      <line style="stroke:#181818;stroke-width:0.5;" x1="2863.15" x2="2934.6038" y1="104.2079" y2="104.2079"/>
     </g>
     <!--class src.models.config.AuthenticationConfiguration-->
     <g id="elem_src.models.config.AuthenticationConfiguration">
@@ -134,13 +134,13 @@
     </g>
     <!--class src.models.config.JsonPathOperator-->
     <g id="elem_src.models.config.JsonPathOperator">
-      <rect codeLine="62" fill="#F1F1F1" height="67.0679" id="src.models.config.JsonPathOperator" rx="2.5" ry="2.5" style="stroke:#181818;stroke-width:0.5;" width="150.0616" x="2678.84" y="305.62"/>
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-      <text fill="#000000" font-family="sans-serif" font-size="14" lengthAdjust="spacing" textLength="118.0616" x="2707.84" y="327.052">JsonPathOperator</text>
-      <line style="stroke:#181818;stroke-width:0.5;" x1="2679.84" x2="2827.9016" y1="337.62" y2="337.62"/>
-      <text fill="#000000" font-family="sans-serif" font-size="14" lengthAdjust="spacing" textLength="37.4919" x="2684.84" y="356.5859">name</text>
-      <line style="stroke:#181818;stroke-width:0.5;" x1="2679.84" x2="2827.9016" y1="364.6879" y2="364.6879"/>
+      <rect codeLine="62" fill="#F1F1F1" height="67.0679" id="src.models.config.JsonPathOperator" rx="2.5" ry="2.5" style="stroke:#181818;stroke-width:0.5;" width="150.0616" x="2695.84" y="305.62"/>
+      <ellipse cx="2710.84" cy="321.62" fill="#ADD1B2" rx="11" ry="11" style="stroke:#181818;stroke-width:1.0;"/>
+      <path d="M2710.9494,317.1513 Q2710.0275,317.1513 2709.2931,317.4638 Q2708.5744,317.7763 2708.0744,318.37 Q2707.5744,318.9481 2707.2931,319.8231 Q2707.0275,320.6981 2707.0275,321.7919 Q2707.0275,323.2294 2707.465,324.2763 Q2707.9181,325.3231 2708.7619,325.87 Q2709.6213,326.4169 2710.9338,326.4169 Q2711.715,326.4169 2712.4025,326.2919 Q2713.1056,326.1513 2714.1056,325.8388 L2714.1056,327.7138 Q2713.2463,328.0419 2712.4806,328.1669 Q2711.7306,328.2919 2710.715,328.2919 Q2708.7931,328.2919 2707.4806,327.495 Q2706.1838,326.6825 2705.5275,325.2138 Q2704.8713,323.7294 2704.8713,321.7606 Q2704.8713,320.3388 2705.2619,319.1669 Q2705.6681,317.9794 2706.4494,317.1044 Q2707.2306,316.2294 2708.3713,315.7606 Q2709.5119,315.2763 2710.9806,315.2763 Q2711.9338,315.2763 2712.8244,315.4794 Q2713.7306,315.6669 2714.6681,316.1356 L2713.84,317.9169 Q2713.0588,317.5419 2712.4025,317.3544 Q2711.7463,317.1513 2710.9494,317.1513 Z " fill="#000000"/>
+      <text fill="#000000" font-family="sans-serif" font-size="14" lengthAdjust="spacing" textLength="118.0616" x="2724.84" y="327.052">JsonPathOperator</text>
+      <line style="stroke:#181818;stroke-width:0.5;" x1="2696.84" x2="2844.9016" y1="337.62" y2="337.62"/>
+      <text fill="#000000" font-family="sans-serif" font-size="14" lengthAdjust="spacing" textLength="37.4919" x="2701.84" y="356.5859">name</text>
+      <line style="stroke:#181818;stroke-width:0.5;" x1="2696.84" x2="2844.9016" y1="364.6879" y2="364.6879"/>
     </g>
     <!--class src.models.config.JwkConfiguration-->
     <g id="elem_src.models.config.JwkConfiguration">
@@ -155,35 +155,37 @@
     </g>
     <!--class src.models.config.JwtConfiguration-->
     <g id="elem_src.models.config.JwtConfiguration">
-      <rect codeLine="69" fill="#F1F1F1" height="105.2038" id="src.models.config.JwtConfiguration" rx="2.5" ry="2.5" style="stroke:#181818;stroke-width:0.5;" width="259.2951" x="2371.23" y="286.55"/>
-      <ellipse cx="2441.1457" cy="302.55" fill="#ADD1B2" rx="11" ry="11" style="stroke:#181818;stroke-width:1.0;"/>
-      <path d="M2441.2551,298.0812 Q2440.3332,298.0812 2439.5989,298.3937 Q2438.8801,298.7062 2438.3801,299.3 Q2437.8801,299.8781 2437.5989,300.7531 Q2437.3332,301.6281 2437.3332,302.7219 Q2437.3332,304.1594 2437.7707,305.2062 Q2438.2239,306.2531 2439.0676,306.8 Q2439.927,307.3469 2441.2395,307.3469 Q2442.0207,307.3469 2442.7082,307.2219 Q2443.4114,307.0812 2444.4114,306.7687 L2444.4114,308.6437 Q2443.552,308.9719 2442.7864,309.0969 Q2442.0364,309.2219 2441.0207,309.2219 Q2439.0989,309.2219 2437.7864,308.425 Q2436.4895,307.6125 2435.8332,306.1437 Q2435.177,304.6594 2435.177,302.6906 Q2435.177,301.2687 2435.5676,300.0969 Q2435.9739,298.9094 2436.7551,298.0344 Q2437.5364,297.1594 2438.677,296.6906 Q2439.8176,296.2062 2441.2864,296.2062 Q2442.2395,296.2062 2443.1301,296.4094 Q2444.0364,296.5969 2444.9739,297.0656 L2444.1457,298.8469 Q2443.3645,298.4719 2442.7082,298.2844 Q2442.052,298.0812 2441.2551,298.0812 Z " fill="#000000"/>
-      <text fill="#000000" font-family="sans-serif" font-size="14" lengthAdjust="spacing" textLength="110.9636" x="2461.6457" y="307.982">JwtConfiguration</text>
-      <line style="stroke:#181818;stroke-width:0.5;" x1="2372.23" x2="2629.5251" y1="318.55" y2="318.55"/>
-      <text fill="#000000" font-family="sans-serif" font-size="14" lengthAdjust="spacing" textLength="247.2951" x="2377.23" y="337.5159">role_rules : Optional[list[JwtRoleRule]]</text>
-      <text fill="#000000" font-family="sans-serif" font-size="14" lengthAdjust="spacing" textLength="117.1516" x="2377.23" y="356.5839">user_id_claim : str</text>
-      <text fill="#000000" font-family="sans-serif" font-size="14" lengthAdjust="spacing" textLength="136.2055" x="2377.23" y="375.6518">username_claim : str</text>
-      <line style="stroke:#181818;stroke-width:0.5;" x1="2372.23" x2="2629.5251" y1="383.7538" y2="383.7538"/>
+      <rect codeLine="69" fill="#F1F1F1" height="105.2038" id="src.models.config.JwtConfiguration" rx="2.5" ry="2.5" style="stroke:#181818;stroke-width:0.5;" width="259.2951" x="2380.23" y="286.55"/>
+      <ellipse cx="2450.1457" cy="302.55" fill="#ADD1B2" rx="11" ry="11" style="stroke:#181818;stroke-width:1.0;"/>
+      <path d="M2450.2551,298.0812 Q2449.3332,298.0812 2448.5989,298.3937 Q2447.8801,298.7062 2447.3801,299.3 Q2446.8801,299.8781 2446.5989,300.7531 Q2446.3332,301.6281 2446.3332,302.7219 Q2446.3332,304.1594 2446.7707,305.2062 Q2447.2239,306.2531 2448.0676,306.8 Q2448.927,307.3469 2450.2395,307.3469 Q2451.0207,307.3469 2451.7082,307.2219 Q2452.4114,307.0812 2453.4114,306.7687 L2453.4114,308.6437 Q2452.552,308.9719 2451.7864,309.0969 Q2451.0364,309.2219 2450.0207,309.2219 Q2448.0989,309.2219 2446.7864,308.425 Q2445.4895,307.6125 2444.8332,306.1437 Q2444.177,304.6594 2444.177,302.6906 Q2444.177,301.2687 2444.5676,300.0969 Q2444.9739,298.9094 2445.7551,298.0344 Q2446.5364,297.1594 2447.677,296.6906 Q2448.8176,296.2062 2450.2864,296.2062 Q2451.2395,296.2062 2452.1301,296.4094 Q2453.0364,296.5969 2453.9739,297.0656 L2453.1457,298.8469 Q2452.3645,298.4719 2451.7082,298.2844 Q2451.052,298.0812 2450.2551,298.0812 Z " fill="#000000"/>
+      <text fill="#000000" font-family="sans-serif" font-size="14" lengthAdjust="spacing" textLength="110.9636" x="2470.6457" y="307.982">JwtConfiguration</text>
+      <line style="stroke:#181818;stroke-width:0.5;" x1="2381.23" x2="2638.5251" y1="318.55" y2="318.55"/>
+      <text fill="#000000" font-family="sans-serif" font-size="14" lengthAdjust="spacing" textLength="247.2951" x="2386.23" y="337.5159">role_rules : Optional[list[JwtRoleRule]]</text>
+      <text fill="#000000" font-family="sans-serif" font-size="14" lengthAdjust="spacing" textLength="117.1516" x="2386.23" y="356.5839">user_id_claim : str</text>
+      <text fill="#000000" font-family="sans-serif" font-size="14" lengthAdjust="spacing" textLength="136.2055" x="2386.23" y="375.6518">username_claim : str</text>
+      <line style="stroke:#181818;stroke-width:0.5;" x1="2381.23" x2="2638.5251" y1="383.7538" y2="383.7538"/>
     </g>
     <!--class src.models.config.JwtRoleRule-->
     <g id="elem_src.models.config.JwtRoleRule">
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-      <path d="M2711.4671,577.6212 Q2710.5453,577.6212 2709.8109,577.9337 Q2709.0921,578.2462 2708.5921,578.84 Q2708.0921,579.4181 2707.8109,580.2931 Q2707.5453,581.1681 2707.5453,582.2619 Q2707.5453,583.6994 2707.9828,584.7462 Q2708.4359,585.7931 2709.2796,586.34 Q2710.139,586.8869 2711.4515,586.8869 Q2712.2328,586.8869 2712.9203,586.7619 Q2713.6234,586.6212 2714.6234,586.3087 L2714.6234,588.1837 Q2713.764,588.5119 2712.9984,588.6369 Q2712.2484,588.7619 2711.2328,588.7619 Q2709.3109,588.7619 2707.9984,587.965 Q2706.7015,587.1525 2706.0453,585.6837 Q2705.389,584.1994 2705.389,582.2306 Q2705.389,580.8087 2705.7796,579.6369 Q2706.1859,578.4494 2706.9671,577.5744 Q2707.7484,576.6994 2708.889,576.2306 Q2710.0296,575.7462 2711.4984,575.7462 Q2712.4515,575.7462 2713.3421,575.9494 Q2714.2484,576.1369 2715.1859,576.6056 L2714.3578,578.3869 Q2713.5765,578.0119 2712.9203,577.8244 Q2712.264,577.6212 2711.4671,577.6212 Z " fill="#000000"/>
-      <text fill="#000000" font-family="sans-serif" font-size="14" lengthAdjust="spacing" textLength="77.4337" x="2730.9639" y="587.522">JwtRoleRule</text>
-      <line style="stroke:#181818;stroke-width:0.5;" x1="2672.13" x2="2835.6254" y1="598.09" y2="598.09"/>
-      <text fill="#000000" font-family="sans-serif" font-size="14" lengthAdjust="spacing" textLength="86.1837" x="2677.13" y="617.0559">jsonpath : str</text>
-      <text fill="#000000" font-family="sans-serif" font-size="14" lengthAdjust="spacing" textLength="86.1557" x="2677.13" y="636.1239">negate : bool</text>
-      <text fill="#000000" font-family="sans-serif" font-size="14" lengthAdjust="spacing" textLength="57.9178" x="2677.13" y="655.1918">operator</text>
-      <text fill="#000000" font-family="sans-serif" font-size="14" lengthAdjust="spacing" textLength="89.2357" x="2677.13" y="674.2597">roles : list[str]</text>
-      <text fill="#000000" font-family="sans-serif" font-size="14" lengthAdjust="spacing" textLength="70.8957" x="2677.13" y="693.3276">value : Any</text>
-      <line style="stroke:#181818;stroke-width:0.5;" x1="2672.13" x2="2835.6254" y1="701.4296" y2="701.4296"/>
-      <text fill="#000000" font-family="sans-serif" font-size="14" lengthAdjust="spacing" textLength="153.4954" x="2677.13" y="720.3955">check_jsonpath() -&gt; Self</text>
-      <text fill="#000000" font-family="sans-serif" font-size="14" lengthAdjust="spacing" textLength="128.3515" x="2677.13" y="739.4634">check_roles() -&gt; Self</text>
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+      <text fill="#000000" font-family="sans-serif" font-size="14" lengthAdjust="spacing" textLength="86.1837" x="2676.58" y="617.0539">jsonpath : str</text>
+      <text fill="#000000" font-family="sans-serif" font-size="14" lengthAdjust="spacing" textLength="86.1557" x="2676.58" y="636.1218">negate : bool</text>
+      <text fill="#000000" font-family="sans-serif" font-size="14" lengthAdjust="spacing" textLength="57.9178" x="2676.58" y="655.1897">operator</text>
+      <text fill="#000000" font-family="sans-serif" font-size="14" lengthAdjust="spacing" textLength="89.2357" x="2676.58" y="674.2576">roles : list[str]</text>
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-      <line style="stroke:#181818;stroke-width:0.5;" x1="2574.05" x2="2799.6993" y1="104.2079" y2="104.2079"/>
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@@ -269,7 +271,7 @@
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@@ -283,160 +285,160 @@
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