diff --git a/crates/goose/src/config/declarative_providers.rs b/crates/goose/src/config/declarative_providers.rs
index 6898eb5e4950..fb0f83d18596 100644
--- a/crates/goose/src/config/declarative_providers.rs
+++ b/crates/goose/src/config/declarative_providers.rs
@@ -207,7 +207,11 @@ pub fn update_custom_provider(params: UpdateCustomProviderParams) -> Result<()>
             api_key_env,
             base_url: params.api_url,
             models: model_infos,
-            headers: params.headers.or(existing_config.headers),
+            headers: match params.headers {
+                Some(h) if h.is_empty() => None,
+                Some(h) => Some(h),
+                None => existing_config.headers,
+            },
             timeout_seconds: existing_config.timeout_seconds,
             supports_streaming: params.supports_streaming,
             requires_auth: params.requires_auth,
diff --git a/ui/desktop/src/components/ChatInput.tsx b/ui/desktop/src/components/ChatInput.tsx
index 760a7862d6da..1e4cd8e6661e 100644
--- a/ui/desktop/src/components/ChatInput.tsx
+++ b/ui/desktop/src/components/ChatInput.tsx
@@ -126,6 +126,7 @@ export default function ChatInput({
   const [displayValue, setDisplayValue] = useState(initialValue); // For immediate visual feedback
   const [isFocused, setIsFocused] = useState(false);
   const [pastedImages, setPastedImages] = useState<PastedImage[]>([]);
+  const [isFilePickerOpen, setIsFilePickerOpen] = useState(false);
 
   // Derived state - chatState != Idle means we're in some form of loading state
   const isLoading = chatState !== ChatState.Idle;
@@ -148,7 +149,6 @@ export default function ChatInput({
   const [diagnosticsOpen, setDiagnosticsOpen] = useState(false);
   const [showCreateRecipeModal, setShowCreateRecipeModal] = useState(false);
   const [showEditRecipeModal, setShowEditRecipeModal] = useState(false);
-  const [isFilePickerOpen, setIsFilePickerOpen] = useState(false);
   const [sessionWorkingDir, setSessionWorkingDir] = useState<string | null>(null);
 
   useEffect(() => {
@@ -1190,13 +1190,11 @@ export default function ChatInput({
 
   return (
     <div
-      className={`flex flex-col relative h-auto p-4 transition-colors ${
-        disableAnimation ? '' : 'page-transition'
-      } ${
-        isFocused
+      className={`flex flex-col relative h-auto p-4 transition-colors ${disableAnimation ? '' : 'page-transition'
+        } ${isFocused
           ? 'border-border-strong hover:border-border-strong'
           : 'border-border-default hover:border-border-default'
-      } bg-background-default z-10 rounded-t-2xl`}
+        } bg-background-default z-10 rounded-t-2xl`}
       data-drop-zone="true"
       onDrop={handleLocalDrop}
       onDragOver={handleLocalDragOver}
@@ -1265,7 +1263,7 @@ export default function ChatInput({
                           size="sm"
                           shape="round"
                           variant="outline"
-                          onClick={() => {}}
+                          onClick={() => { }}
                           disabled={true}
                           className="bg-slate-600 text-white cursor-not-allowed opacity-50 border-slate-600 rounded-full px-6 py-2"
                         >
@@ -1312,13 +1310,12 @@ export default function ChatInput({
                           }
                         }}
                         disabled={isTranscribing}
-                        className={`rounded-full px-6 py-2 ${
-                          isRecording
-                            ? 'bg-red-500 text-white hover:bg-red-600 border-red-500'
-                            : isTranscribing
-                              ? 'bg-slate-600 text-white cursor-not-allowed animate-pulse border-slate-600'
-                              : 'bg-slate-600 text-white hover:bg-slate-700 border-slate-600'
-                        }`}
+                        className={`rounded-full px-6 py-2 ${isRecording
+                          ? 'bg-red-500 text-white hover:bg-red-600 border-red-500'
+                          : isTranscribing
+                            ? 'bg-slate-600 text-white cursor-not-allowed animate-pulse border-slate-600'
+                            : 'bg-slate-600 text-white hover:bg-slate-700 border-slate-600'
+                          }`}
                       >
                         <Microphone />
                       </Button>
@@ -1356,11 +1353,10 @@ export default function ChatInput({
                       shape="round"
                       variant="outline"
                       disabled={isSubmitButtonDisabled}
-                      className={`rounded-full px-10 py-2 flex items-center gap-2 ${
-                        isSubmitButtonDisabled
-                          ? 'bg-slate-600 text-white cursor-not-allowed opacity-50 border-slate-600'
-                          : 'bg-slate-600 text-white hover:bg-slate-700 border-slate-600 hover:cursor-pointer'
-                      }`}
+                      className={`rounded-full px-10 py-2 flex items-center gap-2 ${isSubmitButtonDisabled
+                        ? 'bg-slate-600 text-white cursor-not-allowed opacity-50 border-slate-600'
+                        : 'bg-slate-600 text-white hover:bg-slate-700 border-slate-600 hover:cursor-pointer'
+                        }`}
                     >
                       <Send className="w-4 h-4" />
                       <span className="text-sm">Send</span>
diff --git a/ui/desktop/src/components/settings/extensions/modal/ExtensionModal.tsx b/ui/desktop/src/components/settings/extensions/modal/ExtensionModal.tsx
index 35fe6c2a4141..4968e8d566fd 100644
--- a/ui/desktop/src/components/settings/extensions/modal/ExtensionModal.tsx
+++ b/ui/desktop/src/components/settings/extensions/modal/ExtensionModal.tsx
@@ -156,6 +156,19 @@ export default function ExtensionModal({
   };
 
   const handleHeaderChange = (index: number, field: 'key' | 'value', value: string) => {
+    if (field === 'key') {
+      if (value.includes(' ')) {
+        return;
+      }
+      const trimmedNewKey = value.trim();
+      const normalizedNewKey = trimmedNewKey.toLowerCase();
+      const isDuplicate = formData.headers.some(
+        (h, i) => i !== index && h.key.trim().toLowerCase() === normalizedNewKey,
+      );
+      if (isDuplicate && trimmedNewKey !== '') {
+        return;
+      }
+    }
     const newHeaders = [...formData.headers];
     newHeaders[index][field] = value;
 
diff --git a/ui/desktop/src/components/settings/extensions/modal/HeadersSection.tsx b/ui/desktop/src/components/settings/extensions/modal/HeadersSection.tsx
index 3868f0d4fed3..5b265529f424 100644
--- a/ui/desktop/src/components/settings/extensions/modal/HeadersSection.tsx
+++ b/ui/desktop/src/components/settings/extensions/modal/HeadersSection.tsx
@@ -44,6 +44,10 @@ export default function HeadersSection({
     const keyEmpty = !newKey.trim();
     const valueEmpty = !newValue.trim();
     const keyHasSpaces = newKey.includes(' ');
+    const normalizedNewKey = newKey.trim().toLowerCase();
+    const isDuplicate = headers.some(
+      h => h.key.trim().toLowerCase() === normalizedNewKey
+    );
 
     if (keyEmpty || valueEmpty) {
       setInvalidFields({
@@ -63,6 +67,15 @@ export default function HeadersSection({
       return;
     }
 
+    if (isDuplicate) {
+      setInvalidFields({
+        key: true,
+        value: false,
+      });
+      setValidationError('A header with this name already exists');
+      return;
+    }
+
     setValidationError(null);
     setInvalidFields({ key: false, value: false });
     onAdd(newKey, newValue);
diff --git a/ui/desktop/src/components/settings/extensions/utils.ts b/ui/desktop/src/components/settings/extensions/utils.ts
index b4221ef03275..3ea8bb04cff0 100644
--- a/ui/desktop/src/components/settings/extensions/utils.ts
+++ b/ui/desktop/src/components/settings/extensions/utils.ts
@@ -100,8 +100,8 @@ export function extensionToFormData(extension: FixedExtensionEntry): ExtensionFo
     description: extension.description || '',
     type:
       extension.type === 'frontend' ||
-      extension.type === 'inline_python' ||
-      extension.type === 'platform'
+        extension.type === 'inline_python' ||
+        extension.type === 'platform'
         ? 'stdio'
         : extension.type,
     cmd: extension.type === 'stdio' ? quoteShell([extension.cmd, ...extension.args]) : undefined,
@@ -155,7 +155,7 @@ export function createExtensionConfig(formData: ExtensionFormData): ExtensionCon
       timeout: formData.timeout,
       uri: formData.endpoint || '',
       ...(env_keys.length > 0 ? { env_keys } : {}),
-      ...(Object.keys(headers).length > 0 ? { headers } : {}),
+      headers,
     };
   } else {
     // For other types
diff --git a/ui/desktop/src/components/settings/providers/ProviderGrid.tsx b/ui/desktop/src/components/settings/providers/ProviderGrid.tsx
index ee1e9e4aaac2..a67f69872e88 100644
--- a/ui/desktop/src/components/settings/providers/ProviderGrid.tsx
+++ b/ui/desktop/src/components/settings/providers/ProviderGrid.tsx
@@ -238,6 +238,7 @@ function ProviderCards({
     models: editingProvider.config.models.map((m) => m.name),
     supports_streaming: editingProvider.config.supports_streaming ?? true,
     requires_auth: editingProvider.config.requires_auth ?? true,
+    headers: editingProvider.config.headers ?? undefined,
   };
 
   const editable = editingProvider ? editingProvider.isEditable : true;
@@ -246,7 +247,7 @@ function ProviderCards({
     <>
       {providerCards}
       <Dialog open={showCustomProviderModal} onOpenChange={handleCloseModal}>
-        <DialogContent className="sm:max-w-[600px]">
+        <DialogContent className="sm:max-w-[600px] max-h-[90vh] overflow-y-auto">
           <DialogHeader>
             <DialogTitle>{title}</DialogTitle>
           </DialogHeader>
diff --git a/ui/desktop/src/components/settings/providers/modal/subcomponents/forms/CustomProviderForm.tsx b/ui/desktop/src/components/settings/providers/modal/subcomponents/forms/CustomProviderForm.tsx
index be252a1735d8..78a3ddb433e9 100644
--- a/ui/desktop/src/components/settings/providers/modal/subcomponents/forms/CustomProviderForm.tsx
+++ b/ui/desktop/src/components/settings/providers/modal/subcomponents/forms/CustomProviderForm.tsx
@@ -4,7 +4,8 @@ import { Select } from '../../../../../ui/Select';
 import { Button } from '../../../../../ui/button';
 import { SecureStorageNotice } from '../SecureStorageNotice';
 import { UpdateCustomProviderRequest } from '../../../../../../api';
-import { Trash2, AlertTriangle } from 'lucide-react';
+import { Plus, X, Trash2, AlertTriangle } from 'lucide-react';
+import { cn } from '../../../../../../utils';
 
 interface CustomProviderFormProps {
   onSubmit: (data: UpdateCustomProviderRequest) => void;
@@ -30,6 +31,14 @@ export default function CustomProviderForm({
   const [models, setModels] = useState('');
   const [requiresApiKey, setRequiresApiKey] = useState(false);
   const [supportsStreaming, setSupportsStreaming] = useState(true);
+  const [headers, setHeaders] = useState<{ key: string; value: string }[]>([]);
+  const [newHeaderKey, setNewHeaderKey] = useState('');
+  const [newHeaderValue, setNewHeaderValue] = useState('');
+  const [headerValidationError, setHeaderValidationError] = useState<string | null>(null);
+  const [invalidHeaderFields, setInvalidHeaderFields] = useState<{ key: boolean; value: boolean }>({
+    key: false,
+    value: false,
+  });
   const [validationErrors, setValidationErrors] = useState<Record<string, string>>({});
   const [showDeleteConfirmation, setShowDeleteConfirmation] = useState(false);
 
@@ -46,6 +55,14 @@ export default function CustomProviderForm({
       setModels(initialData.models.join(', '));
       setSupportsStreaming(initialData.supports_streaming ?? true);
       setRequiresApiKey(initialData.requires_auth ?? true);
+
+      if (initialData.headers) {
+        const headerList = Object.entries(initialData.headers).map(([key, value]) => ({
+          key,
+          value,
+        }));
+        setHeaders(headerList);
+      }
     }
   }, [initialData]);
 
@@ -56,6 +73,85 @@ export default function CustomProviderForm({
     }
   };
 
+  const handleAddHeader = () => {
+    const keyEmpty = !newHeaderKey.trim();
+    const valueEmpty = !newHeaderValue.trim();
+    const keyHasSpaces = newHeaderKey.includes(' ');
+    const normalizedNewKey = newHeaderKey.trim().toLowerCase();
+    const isDuplicate = headers.some(h => h.key.trim().toLowerCase() === normalizedNewKey);
+
+    if (keyEmpty || valueEmpty) {
+      setInvalidHeaderFields({
+        key: keyEmpty,
+        value: valueEmpty,
+      });
+      setHeaderValidationError('Both header name and value must be entered');
+      return;
+    }
+
+    if (keyHasSpaces) {
+      setInvalidHeaderFields({
+        key: true,
+        value: false,
+      });
+      setHeaderValidationError('Header name cannot contain spaces');
+      return;
+    }
+
+    if (isDuplicate) {
+      setInvalidHeaderFields({
+        key: true,
+        value: false,
+      });
+      setHeaderValidationError('A header with this name already exists');
+      return;
+    }
+
+    setHeaderValidationError(null);
+    setInvalidHeaderFields({ key: false, value: false });
+    setHeaders([...headers, { key: newHeaderKey, value: newHeaderValue }]);
+    setNewHeaderKey('');
+    setNewHeaderValue('');
+  };
+
+  const handleRemoveHeader = (index: number) => {
+    setHeaders(headers.filter((_, i) => i !== index));
+  };
+
+  const handleHeaderChange = (index: number, field: 'key' | 'value', value: string) => {
+    if (field === 'key') {
+      if (value.includes(' ')) {
+        return;
+      }
+      const normalizedValue = value.trim().toLowerCase();
+      const isDuplicate = headers.some(
+        (h, i) => i !== index && h.key.trim().toLowerCase() === normalizedValue,
+      );
+      if (isDuplicate && normalizedValue !== '') {
+        return;
+      }
+      const updatedHeaders = [...headers];
+      updatedHeaders[index].key = value;
+      setHeaders(updatedHeaders);
+      return;
+    }
+    const updatedHeaders = [...headers];
+    updatedHeaders[index][field] = value;
+    setHeaders(updatedHeaders);
+  };
+
+  const clearHeaderValidation = () => {
+    setHeaderValidationError(null);
+    setInvalidHeaderFields({ key: false, value: false });
+  };
+
+  const handleHeaderKeyDown = (e: React.KeyboardEvent) => {
+    if (e.key === 'Enter') {
+      e.preventDefault();
+      handleAddHeader();
+    }
+  };
+
   const handleSubmit = (e: React.FormEvent) => {
     e.preventDefault();
 
@@ -76,6 +172,30 @@ export default function CustomProviderForm({
       .map((m) => m.trim())
       .filter((m) => m);
 
+    let allHeaders = [...headers];
+
+    if (newHeaderKey.trim() && newHeaderValue.trim()) {
+      const keyHasSpaces = newHeaderKey.includes(' ');
+      const normalizedPendingKey = newHeaderKey.trim().toLowerCase();
+      const isDuplicate = headers.some(
+        (h) => h.key.trim().toLowerCase() === normalizedPendingKey,
+      );
+
+      if (!keyHasSpaces && !isDuplicate) {
+        allHeaders.push({ key: newHeaderKey, value: newHeaderValue });
+      }
+    }
+
+    const headersObject = allHeaders.reduce(
+      (acc, header) => {
+        if (header.key.trim() && header.value.trim()) {
+          acc[header.key.trim()] = header.value.trim();
+        }
+        return acc;
+      },
+      {} as Record<string, string>
+    );
+
     onSubmit({
       engine,
       display_name: displayName,
@@ -84,6 +204,7 @@ export default function CustomProviderForm({
       models: modelList,
       supports_streaming: supportsStreaming,
       requires_auth: requiresApiKey,
+      headers: headersObject,
     });
   };
 
@@ -260,6 +381,79 @@ export default function CustomProviderForm({
               Provider supports streaming responses
             </label>
           </div>
+
+          <div>
+            <label className="text-sm font-medium text-textStandard mb-2 block">
+              Custom Headers
+            </label>
+            <p className="text-xs text-textSubtle mb-4">
+              Add custom HTTP headers to include in requests to the provider. Click the "+" button to add after filling both fields.
+            </p>
+            <div className="grid grid-cols-[1fr_1fr_auto] gap-2 items-center">
+              {headers.map((header, index) => (
+                <React.Fragment key={index}>
+                  <Input
+                    value={header.key}
+                    onChange={(e) => handleHeaderChange(index, 'key', e.target.value)}
+                    placeholder="Header name"
+                    className="w-full text-textStandard border-borderSubtle hover:border-borderStandard"
+                  />
+                  <Input
+                    value={header.value}
+                    onChange={(e) => handleHeaderChange(index, 'value', e.target.value)}
+                    placeholder="Value"
+                    className="w-full text-textStandard border-borderSubtle hover:border-borderStandard"
+                  />
+                  <Button
+                    onClick={() => handleRemoveHeader(index)}
+                    variant="ghost"
+                    type="button"
+                    className="group p-2 h-auto text-iconSubtle hover:bg-transparent"
+                  >
+                    <X className="h-3 w-3 text-gray-400 group-hover:text-white group-hover:drop-shadow-sm transition-all" />
+                  </Button>
+                </React.Fragment>
+              ))}
+
+              <Input
+                value={newHeaderKey}
+                onChange={(e) => {
+                  setNewHeaderKey(e.target.value);
+                  clearHeaderValidation();
+                }}
+                onKeyDown={handleHeaderKeyDown}
+                placeholder="Header name"
+                className={cn(
+                  'w-full text-textStandard border-borderSubtle hover:border-borderStandard',
+                  invalidHeaderFields.key && 'border-red-500 focus:border-red-500'
+                )}
+              />
+              <Input
+                value={newHeaderValue}
+                onChange={(e) => {
+                  setNewHeaderValue(e.target.value);
+                  clearHeaderValidation();
+                }}
+                onKeyDown={handleHeaderKeyDown}
+                placeholder="Value"
+                className={cn(
+                  'w-full text-textStandard border-borderSubtle hover:border-borderStandard',
+                  invalidHeaderFields.value && 'border-red-500 focus:border-red-500'
+                )}
+              />
+              <Button
+                onClick={handleAddHeader}
+                variant="ghost"
+                type="button"
+                className="flex items-center justify-start gap-1 px-2 pr-4 text-sm rounded-full text-textStandard bg-background-default border border-borderSubtle hover:border-borderStandard transition-colors min-w-[60px] h-9 [&>svg]:!size-4"
+              >
+                <Plus /> Add
+              </Button>
+            </div>
+            {headerValidationError && (
+              <div className="mt-2 text-red-500 text-sm">{headerValidationError}</div>
+            )}
+          </div>
         </>
       )}
       <SecureStorageNotice />