diff --git a/client/package.json b/client/package.json
index fd6fc6980..db4358fdd 100644
--- a/client/package.json
+++ b/client/package.json
@@ -33,6 +33,7 @@
     "@radix-ui/react-popover": "^1.1.3",
     "@radix-ui/react-select": "^2.1.2",
     "@radix-ui/react-slot": "^1.1.0",
+    "@radix-ui/react-switch": "^1.2.6",
     "@radix-ui/react-tabs": "^1.1.1",
     "@radix-ui/react-toast": "^1.2.6",
     "@radix-ui/react-tooltip": "^1.1.8",
@@ -69,6 +70,7 @@
     "globals": "^15.9.0",
     "jest": "^29.7.0",
     "jest-environment-jsdom": "^29.7.0",
+    "jest-fixed-jsdom": "^0.0.9",
     "postcss": "^8.5.6",
     "tailwindcss": "^3.4.13",
     "tailwindcss-animate": "^1.0.7",
diff --git a/client/src/App.tsx b/client/src/App.tsx
index 60ce90c51..4c35b0ec1 100644
--- a/client/src/App.tsx
+++ b/client/src/App.tsx
@@ -74,6 +74,10 @@ import ElicitationTab, {
   PendingElicitationRequest,
   ElicitationResponse,
 } from "./components/ElicitationTab";
+import {
+  CustomHeaders,
+  migrateFromLegacyAuth,
+} from "./lib/types/customHeaders";
 
 const CONFIG_LOCAL_STORAGE_KEY = "inspectorConfig_v1";
 
@@ -127,6 +131,39 @@ const App = () => {
     return localStorage.getItem("lastOauthScope") || "";
   });
 
+  // Custom headers state with migration from legacy auth
+  const [customHeaders, setCustomHeaders] = useState<CustomHeaders>(() => {
+    const savedHeaders = localStorage.getItem("lastCustomHeaders");
+    if (savedHeaders) {
+      try {
+        return JSON.parse(savedHeaders);
+      } catch (error) {
+        console.warn(
+          `Failed to parse custom headers: "${savedHeaders}", will try legacy migration`,
+          error,
+        );
+        // Fall back to migration if JSON parsing fails
+      }
+    }
+
+    // Migrate from legacy auth if available
+    const legacyToken = localStorage.getItem("lastBearerToken") || "";
+    const legacyHeaderName = localStorage.getItem("lastHeaderName") || "";
+
+    if (legacyToken) {
+      return migrateFromLegacyAuth(legacyToken, legacyHeaderName);
+    }
+
+    // Default to Authorization: Bearer as the most common case
+    return [
+      {
+        name: "Authorization",
+        value: "Bearer ",
+        enabled: true,
+      },
+    ];
+  });
+
   const [pendingSampleRequests, setPendingSampleRequests] = useState<
     Array<
       PendingRequest & {
@@ -213,8 +250,7 @@ const App = () => {
     args,
     sseUrl,
     env,
-    bearerToken,
-    headerName,
+    customHeaders,
     oauthClientId,
     oauthScope,
     config,
@@ -303,13 +339,38 @@ const App = () => {
   }, [transportType]);
 
   useEffect(() => {
-    localStorage.setItem("lastBearerToken", bearerToken);
+    if (bearerToken) {
+      localStorage.setItem("lastBearerToken", bearerToken);
+    } else {
+      localStorage.removeItem("lastBearerToken");
+    }
   }, [bearerToken]);
 
   useEffect(() => {
-    localStorage.setItem("lastHeaderName", headerName);
+    if (headerName) {
+      localStorage.setItem("lastHeaderName", headerName);
+    } else {
+      localStorage.removeItem("lastHeaderName");
+    }
   }, [headerName]);
 
+  useEffect(() => {
+    localStorage.setItem("lastCustomHeaders", JSON.stringify(customHeaders));
+  }, [customHeaders]);
+
+  // Auto-migrate from legacy auth when custom headers are empty but legacy auth exists
+  useEffect(() => {
+    if (customHeaders.length === 0 && (bearerToken || headerName)) {
+      const migratedHeaders = migrateFromLegacyAuth(bearerToken, headerName);
+      if (migratedHeaders.length > 0) {
+        setCustomHeaders(migratedHeaders);
+        // Clear legacy auth after migration
+        setBearerToken("");
+        setHeaderName("");
+      }
+    }
+  }, [bearerToken, headerName, customHeaders, setCustomHeaders]);
+
   useEffect(() => {
     localStorage.setItem("lastOauthClientId", oauthClientId);
   }, [oauthClientId]);
@@ -810,10 +871,8 @@ const App = () => {
           setEnv={setEnv}
           config={config}
           setConfig={setConfig}
-          bearerToken={bearerToken}
-          setBearerToken={setBearerToken}
-          headerName={headerName}
-          setHeaderName={setHeaderName}
+          customHeaders={customHeaders}
+          setCustomHeaders={setCustomHeaders}
           oauthClientId={oauthClientId}
           setOauthClientId={setOauthClientId}
           oauthScope={oauthScope}
diff --git a/client/src/components/CustomHeaders.tsx b/client/src/components/CustomHeaders.tsx
new file mode 100644
index 000000000..463f7333b
--- /dev/null
+++ b/client/src/components/CustomHeaders.tsx
@@ -0,0 +1,241 @@
+import { useState } from "react";
+import { Button } from "@/components/ui/button";
+import { Input } from "@/components/ui/input";
+import { Textarea } from "@/components/ui/textarea";
+import { Switch } from "@/components/ui/switch";
+import { Plus, Trash2, Eye, EyeOff } from "lucide-react";
+import {
+  CustomHeaders as CustomHeadersType,
+  CustomHeader,
+  createEmptyHeader,
+} from "@/lib/types/customHeaders";
+
+interface CustomHeadersProps {
+  headers: CustomHeadersType;
+  onChange: (headers: CustomHeadersType) => void;
+  className?: string;
+}
+
+const CustomHeaders = ({
+  headers,
+  onChange,
+  className,
+}: CustomHeadersProps) => {
+  const [isJsonMode, setIsJsonMode] = useState(false);
+  const [jsonValue, setJsonValue] = useState("");
+  const [jsonError, setJsonError] = useState<string | null>(null);
+  const [visibleValues, setVisibleValues] = useState<Set<number>>(new Set());
+
+  const updateHeader = (
+    index: number,
+    field: keyof CustomHeader,
+    value: string | boolean,
+  ) => {
+    const newHeaders = [...headers];
+    newHeaders[index] = { ...newHeaders[index], [field]: value };
+    onChange(newHeaders);
+  };
+
+  const addHeader = () => {
+    onChange([...headers, createEmptyHeader()]);
+  };
+
+  const removeHeader = (index: number) => {
+    const newHeaders = headers.filter((_, i) => i !== index);
+    onChange(newHeaders);
+  };
+
+  const toggleValueVisibility = (index: number) => {
+    const newVisible = new Set(visibleValues);
+    if (newVisible.has(index)) {
+      newVisible.delete(index);
+    } else {
+      newVisible.add(index);
+    }
+    setVisibleValues(newVisible);
+  };
+
+  const switchToJsonMode = () => {
+    const jsonObject: Record<string, string> = {};
+    headers.forEach((header) => {
+      if (header.enabled && header.name.trim() && header.value.trim()) {
+        jsonObject[header.name.trim()] = header.value.trim();
+      }
+    });
+    setJsonValue(JSON.stringify(jsonObject, null, 2));
+    setJsonError(null);
+    setIsJsonMode(true);
+  };
+
+  const switchToFormMode = () => {
+    try {
+      const parsed = JSON.parse(jsonValue);
+      if (
+        typeof parsed !== "object" ||
+        parsed === null ||
+        Array.isArray(parsed)
+      ) {
+        setJsonError("JSON must be an object with string key-value pairs");
+        return;
+      }
+
+      const newHeaders: CustomHeadersType = Object.entries(parsed).map(
+        ([name, value]) => ({
+          name,
+          value: String(value),
+          enabled: true,
+        }),
+      );
+
+      onChange(newHeaders);
+      setJsonError(null);
+      setIsJsonMode(false);
+    } catch {
+      setJsonError("Invalid JSON format");
+    }
+  };
+
+  const handleJsonChange = (value: string) => {
+    setJsonValue(value);
+    setJsonError(null);
+  };
+
+  if (isJsonMode) {
+    return (
+      <div className={`space-y-3 ${className}`}>
+        <div className="flex justify-between items-center gap-2">
+          <h4 className="text-sm font-semibold flex-shrink-0">
+            Custom Headers (JSON)
+          </h4>
+          <Button
+            type="button"
+            variant="outline"
+            size="sm"
+            onClick={switchToFormMode}
+            className="flex-shrink-0"
+          >
+            Switch to Form
+          </Button>
+        </div>
+        <div className="space-y-2">
+          <Textarea
+            value={jsonValue}
+            onChange={(e) => handleJsonChange(e.target.value)}
+            placeholder='{\n  "Authorization": "Bearer token123",\n  "X-Tenant-ID": "acme-inc",\n  "X-Environment": "staging"\n}'
+            className="font-mono text-sm min-h-[100px] resize-none"
+          />
+          {jsonError && <p className="text-sm text-red-600">{jsonError}</p>}
+          <p className="text-xs text-muted-foreground">
+            Enter headers as a JSON object with string key-value pairs.
+          </p>
+        </div>
+      </div>
+    );
+  }
+
+  return (
+    <div className={`space-y-3 ${className}`}>
+      <div className="flex justify-between items-center gap-2">
+        <h4 className="text-sm font-semibold flex-shrink-0">Custom Headers</h4>
+        <div className="flex gap-1 flex-shrink-0">
+          <Button
+            type="button"
+            variant="outline"
+            size="sm"
+            onClick={switchToJsonMode}
+            className="text-xs px-2"
+          >
+            JSON
+          </Button>
+          <Button
+            type="button"
+            variant="outline"
+            size="sm"
+            onClick={addHeader}
+            className="text-xs px-2"
+            data-testid="add-header-button"
+          >
+            <Plus className="w-3 h-3 mr-1" />
+            Add
+          </Button>
+        </div>
+      </div>
+
+      {headers.length === 0 ? (
+        <div className="text-center py-4 text-muted-foreground">
+          <p className="text-sm">No custom headers configured</p>
+          <p className="text-xs mt-1">Click "Add" to get started</p>
+        </div>
+      ) : (
+        <div className="space-y-2 max-h-[300px] overflow-y-auto">
+          {headers.map((header, index) => (
+            <div
+              key={index}
+              className="flex items-start gap-2 p-2 border rounded-md"
+            >
+              <Switch
+                checked={header.enabled}
+                onCheckedChange={(enabled) =>
+                  updateHeader(index, "enabled", enabled)
+                }
+                className="shrink-0 mt-2"
+              />
+              <div className="flex-1 min-w-0 space-y-2">
+                <Input
+                  placeholder="Header Name"
+                  value={header.name}
+                  onChange={(e) => updateHeader(index, "name", e.target.value)}
+                  className="font-mono text-xs"
+                  data-testid={`header-name-input-${index}`}
+                />
+                <div className="relative">
+                  <Input
+                    placeholder="Header Value"
+                    value={header.value}
+                    onChange={(e) =>
+                      updateHeader(index, "value", e.target.value)
+                    }
+                    type={visibleValues.has(index) ? "text" : "password"}
+                    className="font-mono text-xs pr-8"
+                    data-testid={`header-value-input-${index}`}
+                  />
+                  <Button
+                    type="button"
+                    variant="ghost"
+                    size="sm"
+                    onClick={() => toggleValueVisibility(index)}
+                    className="absolute right-1 top-1/2 -translate-y-1/2 h-6 w-6 p-0"
+                  >
+                    {visibleValues.has(index) ? (
+                      <EyeOff className="w-3 h-3" />
+                    ) : (
+                      <Eye className="w-3 h-3" />
+                    )}
+                  </Button>
+                </div>
+              </div>
+              <Button
+                type="button"
+                variant="ghost"
+                size="sm"
+                onClick={() => removeHeader(index)}
+                className="shrink-0 text-red-600 hover:text-red-700 hover:bg-red-50 h-6 w-6 p-0 mt-2"
+              >
+                <Trash2 className="w-3 h-3" />
+              </Button>
+            </div>
+          ))}
+        </div>
+      )}
+
+      {headers.length > 0 && (
+        <p className="text-xs text-muted-foreground">
+          Use the toggle to enable/disable headers. Only enabled headers with
+          both name and value will be sent.
+        </p>
+      )}
+    </div>
+  );
+};
+
+export default CustomHeaders;
diff --git a/client/src/components/Sidebar.tsx b/client/src/components/Sidebar.tsx
index 2f53b3aa5..c0c61fbee 100644
--- a/client/src/components/Sidebar.tsx
+++ b/client/src/components/Sidebar.tsx
@@ -37,6 +37,8 @@ import {
   TooltipTrigger,
   TooltipContent,
 } from "@/components/ui/tooltip";
+import CustomHeaders from "./CustomHeaders";
+import { CustomHeaders as CustomHeadersType } from "@/lib/types/customHeaders";
 import { useToast } from "../lib/hooks/useToast";
 
 interface SidebarProps {
@@ -51,10 +53,9 @@ interface SidebarProps {
   setSseUrl: (url: string) => void;
   env: Record<string, string>;
   setEnv: (env: Record<string, string>) => void;
-  bearerToken: string;
-  setBearerToken: (token: string) => void;
-  headerName?: string;
-  setHeaderName?: (name: string) => void;
+  // Custom headers support
+  customHeaders: CustomHeadersType;
+  setCustomHeaders: (headers: CustomHeadersType) => void;
   oauthClientId: string;
   setOauthClientId: (id: string) => void;
   oauthScope: string;
@@ -80,10 +81,8 @@ const Sidebar = ({
   setSseUrl,
   env,
   setEnv,
-  bearerToken,
-  setBearerToken,
-  headerName,
-  setHeaderName,
+  customHeaders,
+  setCustomHeaders,
   oauthClientId,
   setOauthClientId,
   oauthScope,
@@ -499,38 +498,12 @@ const Sidebar = ({
             </Button>
             {showAuthConfig && (
               <>
-                {/* Bearer Token Section */}
-                <div className="space-y-2 p-3 rounded border">
-                  <h4 className="text-sm font-semibold flex items-center">
-                    API Token Authentication
-                  </h4>
-                  <div className="space-y-2">
-                    <label className="text-sm font-medium">Header Name</label>
-                    <Input
-                      placeholder="Authorization"
-                      onChange={(e) =>
-                        setHeaderName && setHeaderName(e.target.value)
-                      }
-                      data-testid="header-input"
-                      className="font-mono"
-                      value={headerName}
-                    />
-                    <label
-                      className="text-sm font-medium"
-                      htmlFor="bearer-token-input"
-                    >
-                      Bearer Token
-                    </label>
-                    <Input
-                      id="bearer-token-input"
-                      placeholder="Bearer Token"
-                      value={bearerToken}
-                      onChange={(e) => setBearerToken(e.target.value)}
-                      data-testid="bearer-token-input"
-                      className="font-mono"
-                      type="password"
-                    />
-                  </div>
+                {/* Custom Headers Section */}
+                <div className="p-3 rounded border overflow-hidden">
+                  <CustomHeaders
+                    headers={customHeaders}
+                    onChange={setCustomHeaders}
+                  />
                 </div>
                 {transportType !== "stdio" && (
                   // OAuth Configuration
diff --git a/client/src/components/__tests__/Sidebar.test.tsx b/client/src/components/__tests__/Sidebar.test.tsx
index 786584d29..3a23daafb 100644
--- a/client/src/components/__tests__/Sidebar.test.tsx
+++ b/client/src/components/__tests__/Sidebar.test.tsx
@@ -48,8 +48,8 @@ describe("Sidebar", () => {
     setOauthScope: jest.fn(),
     env: {},
     setEnv: jest.fn(),
-    bearerToken: "",
-    setBearerToken: jest.fn(),
+    customHeaders: [],
+    setCustomHeaders: jest.fn(),
     onConnect: jest.fn(),
     onDisconnect: jest.fn(),
     stdErrNotifications: [],
@@ -634,117 +634,179 @@ describe("Sidebar", () => {
       fireEvent.click(button);
     };
 
-    it("should update bearer token", () => {
-      const setBearerToken = jest.fn();
+    it("should update bearer token via custom headers", async () => {
+      const setCustomHeaders = jest.fn();
       renderSidebar({
-        bearerToken: "",
-        setBearerToken,
+        customHeaders: [],
+        setCustomHeaders,
         transportType: "sse", // Set transport type to SSE
       });
 
       openAuthSection();
 
-      const tokenInput = screen.getByTestId("bearer-token-input");
-      fireEvent.change(tokenInput, { target: { value: "new_token" } });
+      // Add a new header
+      const addButton = screen.getByTestId("add-header-button");
+      fireEvent.click(addButton);
 
-      expect(setBearerToken).toHaveBeenCalledWith("new_token");
+      // Verify that setCustomHeaders was called to add an empty header
+      expect(setCustomHeaders).toHaveBeenCalledWith([
+        {
+          name: "",
+          value: "",
+          enabled: true,
+        },
+      ]);
     });
 
-    it("should update header name", () => {
-      const setHeaderName = jest.fn();
+    it("should update header name via custom headers", () => {
+      const setCustomHeaders = jest.fn();
       renderSidebar({
-        headerName: "Authorization",
-        setHeaderName,
+        customHeaders: [
+          {
+            name: "Authorization",
+            value: "Bearer token123",
+            enabled: true,
+          },
+        ],
+        setCustomHeaders,
         transportType: "sse",
       });
 
       openAuthSection();
 
-      const headerInput = screen.getByTestId("header-input");
-      fireEvent.change(headerInput, { target: { value: "X-Custom-Auth" } });
+      const headerNameInput = screen.getByTestId("header-name-input-0");
+      fireEvent.change(headerNameInput, { target: { value: "X-Custom-Auth" } });
 
-      expect(setHeaderName).toHaveBeenCalledWith("X-Custom-Auth");
+      expect(setCustomHeaders).toHaveBeenCalledWith([
+        {
+          name: "X-Custom-Auth",
+          value: "Bearer token123",
+          enabled: true,
+        },
+      ]);
     });
 
-    it("should clear bearer token", () => {
-      const setBearerToken = jest.fn();
+    it("should clear bearer token via custom headers", () => {
+      const setCustomHeaders = jest.fn();
       renderSidebar({
-        bearerToken: "existing_token",
-        setBearerToken,
+        customHeaders: [
+          {
+            name: "Authorization",
+            value: "Bearer existing_token",
+            enabled: true,
+          },
+        ],
+        setCustomHeaders,
         transportType: "sse", // Set transport type to SSE
       });
 
       openAuthSection();
 
-      const tokenInput = screen.getByTestId("bearer-token-input");
-      fireEvent.change(tokenInput, { target: { value: "" } });
+      const headerValueInput = screen.getByTestId("header-value-input-0");
+      fireEvent.change(headerValueInput, { target: { value: "" } });
 
-      expect(setBearerToken).toHaveBeenCalledWith("");
+      expect(setCustomHeaders).toHaveBeenCalledWith([
+        {
+          name: "Authorization",
+          value: "",
+          enabled: true,
+        },
+      ]);
     });
 
-    it("should properly render bearer token input", () => {
+    it("should properly render header value input as password field", () => {
       const { rerender } = renderSidebar({
-        bearerToken: "existing_token",
+        customHeaders: [
+          {
+            name: "Authorization",
+            value: "Bearer existing_token",
+            enabled: true,
+          },
+        ],
         transportType: "sse", // Set transport type to SSE
       });
 
       openAuthSection();
 
       // Token input should be a password field
-      const tokenInput = screen.getByTestId("bearer-token-input");
+      const tokenInput = screen.getByTestId("header-value-input-0");
       expect(tokenInput).toHaveProperty("type", "password");
 
       // Update the token
-      fireEvent.change(tokenInput, { target: { value: "new_token" } });
+      fireEvent.change(tokenInput, { target: { value: "Bearer new_token" } });
 
       // Rerender with updated token
       rerender(
         <TooltipProvider>
           <Sidebar
             {...defaultProps}
-            bearerToken="new_token"
+            customHeaders={[
+              {
+                name: "Authorization",
+                value: "Bearer new_token",
+                enabled: true,
+              },
+            ]}
             transportType="sse"
           />
         </TooltipProvider>,
       );
 
       // Token input should still exist after update
-      expect(screen.getByTestId("bearer-token-input")).toBeInTheDocument();
+      expect(screen.getByTestId("header-value-input-0")).toBeInTheDocument();
     });
 
     it("should maintain token visibility state after update", () => {
       const { rerender } = renderSidebar({
-        bearerToken: "existing_token",
+        customHeaders: [
+          {
+            name: "Authorization",
+            value: "Bearer existing_token",
+            enabled: true,
+          },
+        ],
         transportType: "sse", // Set transport type to SSE
       });
 
       openAuthSection();
 
       // Token input should be a password field
-      const tokenInput = screen.getByTestId("bearer-token-input");
+      const tokenInput = screen.getByTestId("header-value-input-0");
       expect(tokenInput).toHaveProperty("type", "password");
 
       // Update the token
-      fireEvent.change(tokenInput, { target: { value: "new_token" } });
+      fireEvent.change(tokenInput, { target: { value: "Bearer new_token" } });
 
       // Rerender with updated token
       rerender(
         <TooltipProvider>
           <Sidebar
             {...defaultProps}
-            bearerToken="new_token"
+            customHeaders={[
+              {
+                name: "Authorization",
+                value: "Bearer new_token",
+                enabled: true,
+              },
+            ]}
             transportType="sse"
           />
         </TooltipProvider>,
       );
 
       // Token input should still exist after update
-      expect(screen.getByTestId("bearer-token-input")).toBeInTheDocument();
+      expect(screen.getByTestId("header-value-input-0")).toBeInTheDocument();
     });
 
     it("should maintain header name when toggling auth section", () => {
       renderSidebar({
-        headerName: "X-API-Key",
+        customHeaders: [
+          {
+            name: "X-API-Key",
+            value: "api-key-123",
+            enabled: true,
+          },
+        ],
         transportType: "sse",
       });
 
@@ -752,7 +814,7 @@ describe("Sidebar", () => {
       openAuthSection();
 
       // Verify header name is displayed
-      const headerInput = screen.getByTestId("header-input");
+      const headerInput = screen.getByTestId("header-name-input-0");
       expect(headerInput).toHaveValue("X-API-Key");
 
       // Close auth section
@@ -763,19 +825,66 @@ describe("Sidebar", () => {
       fireEvent.click(authButton);
 
       // Verify header name is still preserved
-      expect(screen.getByTestId("header-input")).toHaveValue("X-API-Key");
+      expect(screen.getByTestId("header-name-input-0")).toHaveValue(
+        "X-API-Key",
+      );
     });
 
-    it("should display default header name when not specified", () => {
+    it("should display placeholder for header name when no headers exist", () => {
       renderSidebar({
-        headerName: undefined,
+        customHeaders: [],
         transportType: "sse",
       });
 
       openAuthSection();
 
-      const headerInput = screen.getByTestId("header-input");
-      expect(headerInput).toHaveAttribute("placeholder", "Authorization");
+      // Verify that the "No custom headers configured" message is shown
+      expect(
+        screen.getByText("No custom headers configured"),
+      ).toBeInTheDocument();
+      expect(
+        screen.getByText('Click "Add" to get started'),
+      ).toBeInTheDocument();
+
+      // Verify the Add button is present
+      const addButton = screen.getByTestId("add-header-button");
+      expect(addButton).toBeInTheDocument();
+    });
+
+    it("should allow editing existing headers", () => {
+      const setCustomHeaders = jest.fn();
+      renderSidebar({
+        customHeaders: [
+          {
+            name: "Authorization",
+            value: "Bearer token123",
+            enabled: true,
+          },
+        ],
+        setCustomHeaders,
+        transportType: "sse",
+      });
+
+      openAuthSection();
+
+      // Verify header inputs are rendered
+      const headerNameInput = screen.getByTestId("header-name-input-0");
+      const headerValueInput = screen.getByTestId("header-value-input-0");
+
+      expect(headerNameInput).toHaveValue("Authorization");
+      expect(headerValueInput).toHaveValue("Bearer token123");
+      expect(headerNameInput).toHaveAttribute("placeholder", "Header Name");
+      expect(headerValueInput).toHaveAttribute("placeholder", "Header Value");
+
+      // Update header name
+      fireEvent.change(headerNameInput, { target: { value: "X-API-Key" } });
+      expect(setCustomHeaders).toHaveBeenCalledWith([
+        {
+          name: "X-API-Key",
+          value: "Bearer token123",
+          enabled: true,
+        },
+      ]);
     });
   });
 
diff --git a/client/src/components/ui/switch.tsx b/client/src/components/ui/switch.tsx
new file mode 100644
index 000000000..6338184e1
--- /dev/null
+++ b/client/src/components/ui/switch.tsx
@@ -0,0 +1,27 @@
+import * as React from "react";
+import * as SwitchPrimitives from "@radix-ui/react-switch";
+
+import { cn } from "@/lib/utils";
+
+const Switch = React.forwardRef<
+  React.ElementRef<typeof SwitchPrimitives.Root>,
+  React.ComponentPropsWithoutRef<typeof SwitchPrimitives.Root>
+>(({ className, ...props }, ref) => (
+  <SwitchPrimitives.Root
+    className={cn(
+      "peer inline-flex h-5 w-9 shrink-0 cursor-pointer items-center rounded-full border-2 border-transparent shadow-sm transition-colors focus-visible:outline-none focus-visible:ring-2 focus-visible:ring-ring focus-visible:ring-offset-2 focus-visible:ring-offset-background disabled:cursor-not-allowed disabled:opacity-50 data-[state=checked]:bg-primary data-[state=unchecked]:bg-input",
+      className,
+    )}
+    {...props}
+    ref={ref}
+  >
+    <SwitchPrimitives.Thumb
+      className={cn(
+        "pointer-events-none block h-4 w-4 rounded-full bg-background shadow-lg ring-0 transition-transform data-[state=checked]:translate-x-4 data-[state=unchecked]:translate-x-0",
+      )}
+    />
+  </SwitchPrimitives.Root>
+));
+Switch.displayName = SwitchPrimitives.Root.displayName;
+
+export { Switch };
diff --git a/client/src/lib/hooks/__tests__/useConnection.test.tsx b/client/src/lib/hooks/__tests__/useConnection.test.tsx
index 624583dc7..a94f2386a 100644
--- a/client/src/lib/hooks/__tests__/useConnection.test.tsx
+++ b/client/src/lib/hooks/__tests__/useConnection.test.tsx
@@ -13,6 +13,7 @@ import {
 } from "@modelcontextprotocol/sdk/types.js";
 import { auth } from "@modelcontextprotocol/sdk/client/auth.js";
 import { discoverScopes } from "../../auth";
+import { CustomHeaders } from "../../types/customHeaders";
 
 // Mock fetch
 global.fetch = jest.fn().mockResolvedValue({
@@ -648,9 +649,17 @@ describe("useConnection", () => {
     });
 
     test("preserves server Authorization header when proxy auth is configured", async () => {
+      const customHeaders: CustomHeaders = [
+        {
+          name: "Authorization",
+          value: "Bearer server-auth-token",
+          enabled: true,
+        },
+      ];
+
       const propsWithBothAuth = {
         ...defaultProps,
-        bearerToken: "server-auth-token",
+        customHeaders,
         config: {
           ...DEFAULT_INSPECTOR_CONFIG,
           MCP_PROXY_AUTH_TOKEN: {
@@ -740,6 +749,139 @@ describe("useConnection", () => {
     });
   });
 
+  describe("Custom Headers", () => {
+    beforeEach(() => {
+      jest.clearAllMocks();
+      // Reset the mock transport objects
+      mockSSETransport.url = undefined;
+      mockSSETransport.options = undefined;
+      mockStreamableHTTPTransport.url = undefined;
+      mockStreamableHTTPTransport.options = undefined;
+    });
+
+    test("sends multiple custom headers correctly", async () => {
+      const customHeaders: CustomHeaders = [
+        { name: "Authorization", value: "Bearer token123", enabled: true },
+        { name: "X-Tenant-ID", value: "acme-inc", enabled: true },
+        { name: "X-Environment", value: "staging", enabled: true },
+      ];
+
+      const propsWithCustomHeaders = {
+        ...defaultProps,
+        customHeaders,
+      };
+
+      const { result } = renderHook(() =>
+        useConnection(propsWithCustomHeaders),
+      );
+
+      await act(async () => {
+        await result.current.connect();
+      });
+
+      // Check that the transport was created with the correct headers
+      expect(mockSSETransport.options).toBeDefined();
+      expect(mockSSETransport.options?.requestInit?.headers).toBeDefined();
+
+      const headers = mockSSETransport.options?.requestInit?.headers;
+      expect(headers).toHaveProperty("Authorization", "Bearer token123");
+      expect(headers).toHaveProperty("X-Tenant-ID", "acme-inc");
+      expect(headers).toHaveProperty("X-Environment", "staging");
+      expect(headers).toHaveProperty(
+        "x-custom-auth-headers",
+        JSON.stringify(["X-Tenant-ID", "X-Environment"]),
+      );
+    });
+
+    test("ignores disabled custom headers", async () => {
+      const customHeaders: CustomHeaders = [
+        { name: "Authorization", value: "Bearer token123", enabled: true },
+        { name: "X-Disabled", value: "should-not-appear", enabled: false },
+        { name: "X-Enabled", value: "should-appear", enabled: true },
+      ];
+
+      const propsWithCustomHeaders = {
+        ...defaultProps,
+        customHeaders,
+      };
+
+      const { result } = renderHook(() =>
+        useConnection(propsWithCustomHeaders),
+      );
+
+      await act(async () => {
+        await result.current.connect();
+      });
+
+      const headers = mockSSETransport.options?.requestInit?.headers;
+      expect(headers).toHaveProperty("Authorization", "Bearer token123");
+      expect(headers).toHaveProperty("X-Enabled", "should-appear");
+      expect(headers).not.toHaveProperty("X-Disabled");
+    });
+
+    test("handles migrated legacy auth via custom headers", async () => {
+      // Simulate what App.tsx would do - migrate legacy auth to custom headers
+      const customHeaders: CustomHeaders = [
+        { name: "X-Custom-Auth", value: "legacy-token", enabled: true },
+      ];
+
+      const propsWithMigratedAuth = {
+        ...defaultProps,
+        customHeaders,
+      };
+
+      const { result } = renderHook(() => useConnection(propsWithMigratedAuth));
+
+      await act(async () => {
+        await result.current.connect();
+      });
+
+      const headers = mockSSETransport.options?.requestInit?.headers;
+      expect(headers).toHaveProperty("X-Custom-Auth", "legacy-token");
+      expect(headers).toHaveProperty(
+        "x-custom-auth-headers",
+        JSON.stringify(["X-Custom-Auth"]),
+      );
+    });
+
+    test("uses OAuth token when no custom headers or legacy auth provided", async () => {
+      const propsWithoutAuth = {
+        ...defaultProps,
+      };
+
+      const { result } = renderHook(() => useConnection(propsWithoutAuth));
+
+      await act(async () => {
+        await result.current.connect();
+      });
+
+      const headers = mockSSETransport.options?.requestInit?.headers;
+      expect(headers).toHaveProperty("Authorization", "Bearer mock-token");
+    });
+
+    test("prioritizes custom headers over legacy auth", async () => {
+      const customHeaders: CustomHeaders = [
+        { name: "Authorization", value: "Bearer custom-token", enabled: true },
+      ];
+
+      const propsWithBothAuth = {
+        ...defaultProps,
+        customHeaders,
+        bearerToken: "legacy-token",
+        headerName: "Authorization",
+      };
+
+      const { result } = renderHook(() => useConnection(propsWithBothAuth));
+
+      await act(async () => {
+        await result.current.connect();
+      });
+
+      const headers = mockSSETransport.options?.requestInit?.headers;
+      expect(headers).toHaveProperty("Authorization", "Bearer custom-token");
+    });
+  });
+
   describe("OAuth Error Handling with Scope Discovery", () => {
     beforeEach(() => {
       jest.clearAllMocks();
diff --git a/client/src/lib/hooks/useConnection.ts b/client/src/lib/hooks/useConnection.ts
index bfb72941c..f47f0d15d 100644
--- a/client/src/lib/hooks/useConnection.ts
+++ b/client/src/lib/hooks/useConnection.ts
@@ -57,6 +57,7 @@ import {
 import { getMCPServerRequestTimeout } from "@/utils/configUtils";
 import { InspectorConfig } from "../configurationTypes";
 import { Transport } from "@modelcontextprotocol/sdk/shared/transport.js";
+import { CustomHeaders } from "../types/customHeaders";
 
 interface UseConnectionOptions {
   transportType: "stdio" | "sse" | "streamable-http";
@@ -64,8 +65,8 @@ interface UseConnectionOptions {
   args: string;
   sseUrl: string;
   env: Record<string, string>;
-  bearerToken?: string;
-  headerName?: string;
+  // Custom headers support
+  customHeaders?: CustomHeaders;
   oauthClientId?: string;
   oauthScope?: string;
   config: InspectorConfig;
@@ -86,8 +87,7 @@ export function useConnection({
   args,
   sseUrl,
   env,
-  bearerToken,
-  headerName,
+  customHeaders,
   oauthClientId,
   oauthScope,
   config,
@@ -379,21 +379,44 @@ export function useConnection({
       // Create an auth provider with the current server URL
       const serverAuthProvider = new InspectorOAuthClientProvider(sseUrl);
 
-      // Use manually provided bearer token if available, otherwise use OAuth tokens
-      const token =
-        bearerToken || (await serverAuthProvider.tokens())?.access_token;
-      if (token) {
-        const authHeaderName = headerName || "Authorization";
-
-        // Add custom header name as a special request header to let the server know which header to pass through
-        if (authHeaderName.toLowerCase() !== "authorization") {
-          headers[authHeaderName] = token;
-          headers["x-custom-auth-header"] = authHeaderName;
-        } else {
-          headers[authHeaderName] = `Bearer ${token}`;
+      // Use custom headers (migration is handled in App.tsx)
+      let finalHeaders: CustomHeaders = customHeaders || [];
+
+      // Add OAuth token if available and no custom headers are set
+      if (finalHeaders.length === 0) {
+        const oauthToken = (await serverAuthProvider.tokens())?.access_token;
+        if (oauthToken) {
+          finalHeaders = [
+            {
+              name: "Authorization",
+              value: `Bearer ${oauthToken}`,
+              enabled: true,
+            },
+          ];
         }
       }
 
+      // Process all enabled custom headers
+      const customHeaderNames: string[] = [];
+      finalHeaders.forEach((header) => {
+        if (header.enabled && header.name.trim() && header.value.trim()) {
+          const headerName = header.name.trim();
+          const headerValue = header.value.trim();
+
+          headers[headerName] = headerValue;
+
+          // Track custom header names for server processing
+          if (headerName.toLowerCase() !== "authorization") {
+            customHeaderNames.push(headerName);
+          }
+        }
+      });
+
+      // Add custom header names as a special request header for server processing
+      if (customHeaderNames.length > 0) {
+        headers["x-custom-auth-headers"] = JSON.stringify(customHeaderNames);
+      }
+
       // Add proxy authentication
       const { token: proxyAuthToken, header: proxyAuthTokenHeader } =
         getMCPProxyAuthToken(config);
diff --git a/client/src/lib/types/customHeaders.ts b/client/src/lib/types/customHeaders.ts
new file mode 100644
index 000000000..46e7237d0
--- /dev/null
+++ b/client/src/lib/types/customHeaders.ts
@@ -0,0 +1,64 @@
+export interface CustomHeader {
+  name: string;
+  value: string;
+  enabled: boolean;
+}
+
+export type CustomHeaders = CustomHeader[];
+
+export const createEmptyHeader = (): CustomHeader => ({
+  name: "",
+  value: "",
+  enabled: true,
+});
+
+export const createHeaderFromBearerToken = (
+  bearerToken: string,
+  headerName?: string,
+): CustomHeader => ({
+  name: headerName || "Authorization",
+  value:
+    headerName?.toLowerCase() === "authorization" || !headerName
+      ? `Bearer ${bearerToken}`
+      : bearerToken,
+  enabled: true,
+});
+
+export const getEnabledHeaders = (headers: CustomHeaders): CustomHeaders => {
+  return headers.filter(
+    (header) => header.enabled && header.name.trim() && header.value.trim(),
+  );
+};
+
+export const headersToRecord = (
+  headers: CustomHeaders,
+): Record<string, string> => {
+  const enabledHeaders = getEnabledHeaders(headers);
+  const record: Record<string, string> = {};
+
+  enabledHeaders.forEach((header) => {
+    record[header.name.trim()] = header.value.trim();
+  });
+
+  return record;
+};
+
+export const recordToHeaders = (
+  record: Record<string, string>,
+): CustomHeaders => {
+  return Object.entries(record).map(([name, value]) => ({
+    name,
+    value,
+    enabled: true,
+  }));
+};
+
+// Migration helper for backward compatibility
+export const migrateFromLegacyAuth = (
+  bearerToken?: string,
+  headerName?: string,
+): CustomHeaders => {
+  return bearerToken
+    ? [createHeaderFromBearerToken(bearerToken, headerName)]
+    : [];
+};
diff --git a/package-lock.json b/package-lock.json
index e2070a9b4..d422148bb 100644
--- a/package-lock.json
+++ b/package-lock.json
@@ -80,6 +80,7 @@
         "@radix-ui/react-popover": "^1.1.3",
         "@radix-ui/react-select": "^2.1.2",
         "@radix-ui/react-slot": "^1.1.0",
+        "@radix-ui/react-switch": "^1.2.6",
         "@radix-ui/react-tabs": "^1.1.1",
         "@radix-ui/react-toast": "^1.2.6",
         "@radix-ui/react-tooltip": "^1.1.8",
@@ -119,6 +120,7 @@
         "globals": "^15.9.0",
         "jest": "^29.7.0",
         "jest-environment-jsdom": "^29.7.0",
+        "jest-fixed-jsdom": "^0.0.9",
         "postcss": "^8.5.6",
         "tailwindcss": "^3.4.13",
         "tailwindcss-animate": "^1.0.7",
@@ -2619,6 +2621,41 @@
         }
       }
     },
+    "node_modules/@radix-ui/react-switch": {
+      "version": "1.2.6",
+      "resolved": "https://registry.npmjs.org/@radix-ui/react-switch/-/react-switch-1.2.6.tgz",
+      "integrity": "sha512-bByzr1+ep1zk4VubeEVViV592vu2lHE2BZY5OnzehZqOOgogN80+mNtCqPkhn2gklJqOpxWgPoYTSnhBCqpOXQ==",
+      "license": "MIT",
+      "dependencies": {
+        "@radix-ui/primitive": "1.1.3",
+        "@radix-ui/react-compose-refs": "1.1.2",
+        "@radix-ui/react-context": "1.1.2",
+        "@radix-ui/react-primitive": "2.1.3",
+        "@radix-ui/react-use-controllable-state": "1.2.2",
+        "@radix-ui/react-use-previous": "1.1.1",
+        "@radix-ui/react-use-size": "1.1.1"
+      },
+      "peerDependencies": {
+        "@types/react": "*",
+        "@types/react-dom": "*",
+        "react": "^16.8 || ^17.0 || ^18.0 || ^19.0 || ^19.0.0-rc",
+        "react-dom": "^16.8 || ^17.0 || ^18.0 || ^19.0 || ^19.0.0-rc"
+      },
+      "peerDependenciesMeta": {
+        "@types/react": {
+          "optional": true
+        },
+        "@types/react-dom": {
+          "optional": true
+        }
+      }
+    },
+    "node_modules/@radix-ui/react-switch/node_modules/@radix-ui/primitive": {
+      "version": "1.1.3",
+      "resolved": "https://registry.npmjs.org/@radix-ui/primitive/-/primitive-1.1.3.tgz",
+      "integrity": "sha512-JTF99U/6XIjCBo0wqkU5sK10glYe27MRRsfwoiq5zzOEZLHU3A3KCMa5X/azekYRCJ0HlwI0crAXS/5dEHTzDg==",
+      "license": "MIT"
+    },
     "node_modules/@radix-ui/react-tabs": {
       "version": "1.1.12",
       "resolved": "https://registry.npmjs.org/@radix-ui/react-tabs/-/react-tabs-1.1.12.tgz",
@@ -11752,6 +11789,8 @@
         "@modelcontextprotocol/sdk": "^1.18.0",
         "cors": "^2.8.5",
         "express": "^5.1.0",
+        "shell-quote": "^1.8.3",
+        "spawn-rx": "^5.1.2",
         "ws": "^8.18.0",
         "zod": "^3.25.76"
       },
@@ -11761,6 +11800,7 @@
       "devDependencies": {
         "@types/cors": "^2.8.19",
         "@types/express": "^4.17.23",
+        "@types/shell-quote": "^1.7.5",
         "@types/ws": "^8.5.12",
         "tsx": "^4.19.0",
         "typescript": "^5.6.2"
diff --git a/server/package.json b/server/package.json
index b46f94fb1..528bee70e 100644
--- a/server/package.json
+++ b/server/package.json
@@ -22,6 +22,7 @@
   "devDependencies": {
     "@types/cors": "^2.8.19",
     "@types/express": "^4.17.23",
+    "@types/shell-quote": "^1.7.5",
     "@types/ws": "^8.5.12",
     "tsx": "^4.19.0",
     "typescript": "^5.6.2"
@@ -30,6 +31,8 @@
     "@modelcontextprotocol/sdk": "^1.18.0",
     "cors": "^2.8.5",
     "express": "^5.1.0",
+    "shell-quote": "^1.8.3",
+    "spawn-rx": "^5.1.2",
     "ws": "^8.18.0",
     "zod": "^3.25.76"
   }
diff --git a/server/src/index.ts b/server/src/index.ts
index 3f739f39e..af3ea9284 100644
--- a/server/src/index.ts
+++ b/server/src/index.ts
@@ -90,6 +90,27 @@ const getHttpHeaders = (req: express.Request): Record<string, string> => {
     }
   }
 
+  // Handle multiple custom headers (new approach)
+  if (req.headers["x-custom-auth-headers"] !== undefined) {
+    try {
+      const customHeaderNames = JSON.parse(
+        req.headers["x-custom-auth-headers"] as string,
+      ) as string[];
+      if (Array.isArray(customHeaderNames)) {
+        customHeaderNames.forEach((headerName) => {
+          const lowerCaseHeaderName = headerName.toLowerCase();
+          if (req.headers[lowerCaseHeaderName] !== undefined) {
+            const value = req.headers[lowerCaseHeaderName];
+            headers[headerName] = Array.isArray(value)
+              ? value[value.length - 1]
+              : value;
+          }
+        });
+      }
+    } catch (error) {
+      console.warn("Failed to parse x-custom-auth-headers:", error);
+    }
+  }
   return headers;
 };