diff --git a/apps/sim/app/o/[organizationId]/components/organization-sidebar/components/organization-header/organization-header.test.tsx b/apps/sim/app/o/[organizationId]/components/organization-sidebar/components/organization-header/organization-header.test.tsx
index d4b263d4f01..665eea639dc 100644
--- a/apps/sim/app/o/[organizationId]/components/organization-sidebar/components/organization-header/organization-header.test.tsx
+++ b/apps/sim/app/o/[organizationId]/components/organization-sidebar/components/organization-header/organization-header.test.tsx
@@ -49,7 +49,7 @@ afterEach(async () => {
   vi.unstubAllGlobals()
 })
 
-async function render(canEditLogo = true) {
+async function render(canEditLogo = true, isCollapsed = false, onExpandSidebar = vi.fn()) {
   await act(async () => {
     root.render(
       <QueryClientProvider client={queryClient}>
@@ -57,8 +57,8 @@ async function render(canEditLogo = true) {
           <OrganizationHeader
             organization={organization}
             canEditLogo={canEditLogo}
-            isCollapsed={false}
-            onExpandSidebar={vi.fn()}
+            isCollapsed={isCollapsed}
+            onExpandSidebar={onExpandSidebar}
           />
         </ToastProvider>
       </QueryClientProvider>
@@ -74,9 +74,9 @@ async function openMenu() {
   })
 }
 
-function menuItem(name: string) {
-  return Array.from(document.querySelectorAll<HTMLElement>('[role="menuitem"]')).find(
-    (item) => item.textContent === name
+function logoControl() {
+  return document.querySelector<HTMLElement>(
+    '[role="menuitem"][aria-label="Change organization logo"]'
   )
 }
 
@@ -87,21 +87,70 @@ async function pickFile(file: File) {
 }
 
 describe('OrganizationHeader logo upload', () => {
-  it('opens the same native file picker from the admin menu', async () => {
+  it('opens the native file picker by clicking the logo and keeps the menu open', async () => {
     await render()
     await openMenu()
     const input = container.querySelector<HTMLInputElement>('input[type="file"]')!
     const click = vi.spyOn(input, 'click').mockImplementation(() => {})
     expect(input.accept).toContain('image/png')
-    await act(async () => menuItem('Upload logo')!.click())
+    await act(async () => logoControl()!.click())
+    expect(click).toHaveBeenCalledOnce()
+    expect(logoControl()).not.toBeNull()
+    expect(document.body.textContent).not.toContain('Upload logo')
+    expect(document.querySelector('[role="menu"]')?.textContent).toContain('Settings')
+  })
+
+  it.each(['Enter', ' '])('opens the file picker using the %j key', async (key) => {
+    await render()
+    await openMenu()
+    const input = container.querySelector<HTMLInputElement>('input[type="file"]')!
+    const click = vi.spyOn(input, 'click').mockImplementation(() => {})
+    await act(async () => {
+      logoControl()!.focus()
+      logoControl()!.dispatchEvent(new KeyboardEvent('keydown', { key, bubbles: true }))
+    })
     expect(click).toHaveBeenCalledOnce()
   })
 
   it('does not offer logo changes to members', async () => {
     await render(false)
     await openMenu()
-    expect(menuItem('Upload logo')).toBeUndefined()
+    expect(logoControl()).toBeNull()
+    expect(container.querySelector('input[type="file"]')).toBeNull()
+    expect(document.querySelector('[role="menu"]')?.textContent).toContain('Design')
+  })
+
+  it('preserves the collapsed logo as the sidebar expand control', async () => {
+    const expand = vi.fn()
+    await render(true, true, expand)
+    await act(async () => {
+      container.querySelector<HTMLButtonElement>('[aria-label="Expand sidebar"]')!.click()
+    })
+    expect(expand).toHaveBeenCalledOnce()
     expect(container.querySelector('input[type="file"]')).toBeNull()
+    expect(mocks.upload).not.toHaveBeenCalled()
+  })
+
+  it('disables logo changes while the upload is pending', async () => {
+    let completeUpload!: () => void
+    mocks.upload.mockImplementation(
+      () =>
+        new Promise<void>((resolve) => {
+          completeUpload = resolve
+        })
+    )
+    await render()
+    await openMenu()
+    await pickFile(new File(['image'], 'logo.png', { type: 'image/png' }))
+    await act(async () => {
+      await vi.waitFor(() => expect(logoControl()?.getAttribute('aria-disabled')).toBe('true'))
+    })
+    expect(logoControl()?.getAttribute('aria-busy')).toBe('true')
+    expect(container.querySelector<HTMLInputElement>('input[type="file"]')!.disabled).toBe(true)
+    await act(async () => logoControl()!.click())
+    expect(mocks.upload).toHaveBeenCalledOnce()
+    await act(async () => completeUpload())
+    expect(mocks.refresh).toHaveBeenCalledOnce()
   })
 
   it('uploads under the organization scope and refreshes its identity after success', async () => {
diff --git a/apps/sim/app/o/[organizationId]/components/organization-sidebar/components/organization-header/organization-header.tsx b/apps/sim/app/o/[organizationId]/components/organization-sidebar/components/organization-header/organization-header.tsx
index de00a944798..19a580ae22b 100644
--- a/apps/sim/app/o/[organizationId]/components/organization-sidebar/components/organization-header/organization-header.tsx
+++ b/apps/sim/app/o/[organizationId]/components/organization-sidebar/components/organization-header/organization-header.tsx
@@ -9,9 +9,10 @@ import {
   DropdownMenuItem,
   DropdownMenuTrigger,
   OverflowText,
+  Tooltip,
   toast,
 } from '@sim/emcn'
-import { PanelLeft, Settings, Upload } from '@sim/emcn/icons'
+import { PanelLeft, Settings } from '@sim/emcn/icons'
 import { useRouter } from 'next/navigation'
 import { IdentityTile } from '@/components/identity-tile/identity-tile'
 import { getOrganizationSettingsHref } from '@/components/settings/navigation'
@@ -80,6 +81,9 @@ export function OrganizationHeader({
   }
 
   const { memberCount } = organization
+  const logo = (
+    <IdentityTile size='lg' initial={initial} logoUrl={organization.logo} alt={organization.name} />
+  )
 
   return (
     <div className='min-w-0 flex-1'>
@@ -120,12 +124,30 @@ export function OrganizationHeader({
           className='w-64 max-w-[calc(100vw-24px)]'
         >
           <div className='flex items-center gap-2 px-2 py-1.5'>
-            <IdentityTile
-              size='lg'
-              initial={initial}
-              logoUrl={organization.logo}
-              alt={organization.name}
-            />
+            {canEditLogo ? (
+              <Tooltip.Root>
+                <Tooltip.Trigger asChild>
+                  <DropdownMenuItem
+                    aria-label='Change organization logo'
+                    aria-busy={isUploadingLogo}
+                    textValue='Change organization logo'
+                    className='h-auto shrink-0 p-1'
+                    disabled={isUploadingLogo}
+                    onSelect={(event) => {
+                      event.preventDefault()
+                      fileInputRef.current?.click()
+                    }}
+                  >
+                    {logo}
+                  </DropdownMenuItem>
+                </Tooltip.Trigger>
+                <Tooltip.Content>
+                  {isUploadingLogo ? 'Uploading...' : 'Change logo'}
+                </Tooltip.Content>
+              </Tooltip.Root>
+            ) : (
+              logo
+            )}
             <div className='flex min-w-0 flex-col'>
               <OverflowText label={organization.name} />
               <span className='text-[var(--text-muted)] text-caption'>
@@ -133,15 +155,6 @@ export function OrganizationHeader({
               </span>
             </div>
           </div>
-          {canEditLogo && (
-            <DropdownMenuItem
-              disabled={isUploadingLogo}
-              onSelect={() => fileInputRef.current?.click()}
-            >
-              <Upload className='size-[14px]' />
-              {isUploadingLogo ? 'Uploading...' : 'Upload logo'}
-            </DropdownMenuItem>
-          )}
           <DropdownMenuItem asChild>
             <SettingsGuardedLink href={getOrganizationSettingsHref(organization.id, 'members')}>
               <Settings className='size-[14px]' />