diff --git a/src/main/skills/managed-skill-fallback-message.ts b/src/main/skills/managed-skill-fallback-message.ts
index 215caa9faed..269239957cc 100644
--- a/src/main/skills/managed-skill-fallback-message.ts
+++ b/src/main/skills/managed-skill-fallback-message.ts
@@ -3,46 +3,46 @@ import type { ManagedAgentSkillFallbackReason } from '../../shared/skills'
 export function getManagedSkillFallbackMessage(reason: ManagedAgentSkillFallbackReason): string {
   switch (reason) {
     case 'target-required':
-      return 'Orca could not resolve the runtime that should read this skill.'
+      return "Orca couldn't tell which runtime should use this skill."
     case 'unsupported-skill':
-      return 'This is not an Orca-managed agent skill.'
+      return "This isn't an Orca-managed skill."
     case 'repair-required-runtime':
-      return 'The selected runtime needs repair before Orca can inspect its skills.'
+      return 'This runtime needs repair before Orca can inspect its skills.'
     case 'remote-runtime':
-      return 'Remote runtimes are not updated in the background.'
+      return 'This skill is on a remote runtime, so Orca needs you to update it there.'
     case 'wsl-runtime':
-      return 'WSL skill updates are manual in this version.'
+      return 'This skill is in WSL, so Orca needs you to update it there.'
     case 'missing-install':
-      return 'The managed skill is not installed in the selected runtime.'
+      return "This skill isn't installed for this runtime yet."
     case 'project-install':
-      return 'Project-scoped skills are not updated in the background.'
+      return "This skill is installed in the project, so Orca won't update it automatically."
     case 'ambiguous-install':
-      return 'Orca found both global and project-scoped copies of this skill.'
+      return 'Orca found more than one copy of this skill and needs you to choose the right one.'
     case 'bundled-or-plugin-install':
-      return 'Bundled and plugin-cache skills are not mutated by Orca.'
+      return "This skill comes from Orca or a plugin, so Orca won't modify it here."
     case 'symlinked-global-install':
-      return 'Symlinked global skills are not safe for background updates yet.'
+      return "This global skill is symlinked, so Orca won't change it automatically."
     case 'unsupported-cli-contract':
-      return 'This build does not include the verified skills CLI update contract.'
+      return "This Orca build can't verify skill updates yet."
     case 'expected-hash-missing':
-      return 'This build does not include an expected hash for this managed skill.'
+      return "This Orca build can't verify the expected version of this skill."
     case 'lockfile-missing':
-      return 'Orca could not find the global skills lockfile.'
+      return "Orca couldn't find the global skills lockfile needed to verify this update."
     case 'lockfile-malformed':
-      return 'The global skills lockfile could not be parsed.'
+      return "Orca couldn't read the global skills lockfile needed to verify this update."
     case 'lockfile-unsupported-schema':
-      return 'The global skills lockfile uses an unsupported schema version.'
+      return "The global skills lockfile uses a format Orca doesn't support yet."
     case 'lock-entry-missing':
-      return 'The global skills lockfile does not track this skill.'
+      return "The global skills lockfile doesn't track this skill, so Orca can't verify the update."
     case 'lock-entry-unmanaged-source':
-      return 'The installed skill is not tracked as Orca-managed source.'
+      return "This installed skill isn't tracked as Orca-managed, so Orca won't update it automatically."
     case 'background-update-disabled':
-      return 'Automatic skill updates are turned off, so this update needs manual review.'
+      return 'Automatic skill updates are off, so Orca needs you to run this update.'
     case 'cooldown':
       return 'Orca recently tried this managed-skill check and is cooling down.'
     case 'update-failed':
-      return 'The managed-skill update command failed.'
+      return 'Orca tried to update this skill automatically, but the command failed.'
     case 'update-timeout':
-      return 'The managed-skill update command timed out.'
+      return 'Orca tried to update this skill automatically, but the command timed out.'
   }
 }
diff --git a/src/renderer/src/components/settings/AgentSkillSetupPanel.test.tsx b/src/renderer/src/components/settings/AgentSkillSetupPanel.test.tsx
index b21e7a9b9ec..bbf320f38cb 100644
--- a/src/renderer/src/components/settings/AgentSkillSetupPanel.test.tsx
+++ b/src/renderer/src/components/settings/AgentSkillSetupPanel.test.tsx
@@ -218,6 +218,13 @@ describe('AgentSkillSetupPanel', () => {
     expect(buttonMarkupByLabel(html, 'Install')).toContain('disabled=""')
   })
 
+  it('omits description copy when the enclosing surface already provides context', () => {
+    const html = renderPanel({ description: undefined, hideHeader: true })
+
+    expect(html).not.toContain('Enables agents to use Orca workflows.')
+    expect(buttonLabels(html)).toEqual(['Install', 'Re-check'])
+  })
+
   it('opens not-installed setup with the install command for preview, copy, and terminal', async () => {
     await renderInteractivePanel({ installedCommand: UPDATE_COMMAND })
 
diff --git a/src/renderer/src/components/settings/AgentSkillSetupPanel.tsx b/src/renderer/src/components/settings/AgentSkillSetupPanel.tsx
index 1453eaf02e4..ddb153ec449 100644
--- a/src/renderer/src/components/settings/AgentSkillSetupPanel.tsx
+++ b/src/renderer/src/components/settings/AgentSkillSetupPanel.tsx
@@ -16,7 +16,7 @@ type SkillPrerequisiteStatus = Awaited<ReturnType<typeof window.api.cli.getInsta
 
 type AgentSkillSetupPanelProps = {
   title: string
-  description: ReactNode
+  description?: ReactNode
   command: string
   installedCommand?: string
   terminalTitle: string
@@ -253,7 +253,9 @@ export function AgentSkillSetupPanel({
           </div>
         )}
         <div className={cn('max-w-none', hideHeader ? null : 'mt-3')}>
-          <p className="text-[13px] leading-snug text-muted-foreground">{description}</p>
+          {description ? (
+            <p className="text-[13px] leading-snug text-muted-foreground">{description}</p>
+          ) : null}
           {actionRow}
           {actionHint ? <div className="mt-2">{actionHint}</div> : null}
           {!installed && preInstallNotice && preInstallNoticeVisible ? (
diff --git a/src/renderer/src/components/skills/ManagedAgentSkillSetupDialogHost.test.ts b/src/renderer/src/components/skills/ManagedAgentSkillSetupDialogHost.test.ts
index 3a2f8f9479f..a786c070b35 100644
--- a/src/renderer/src/components/skills/ManagedAgentSkillSetupDialogHost.test.ts
+++ b/src/renderer/src/components/skills/ManagedAgentSkillSetupDialogHost.test.ts
@@ -2,7 +2,8 @@ import { beforeEach, describe, expect, it, vi } from 'vitest'
 import type { ManagedAgentSkillFallback } from '../../../../shared/skills'
 import {
   getManagedSkillFallbackDisplayMessage,
-  getManagedSkillContextCopy
+  getManagedSkillContextCopy,
+  getManagedSkillContextWorkspaceCopy
 } from './managed-agent-skill-dialog-copy'
 import {
   advanceManagedAgentSkillFallbackQueue,
@@ -52,21 +53,28 @@ beforeEach(() => {
 })
 
 describe('ManagedAgentSkillSetupDialogHost copy', () => {
-  it('names the agent-triggered orchestration context', () => {
-    expect(getManagedSkillContextCopy('agent-orchestration')).toBe(
-      'An agent just tried to use Orca orchestration. Orca needs the orchestration skill before agents can coordinate reliably.'
+  it('uses neutral orchestration context copy when no workspace is available', () => {
+    expect(getManagedSkillContextCopy('agent-orchestration', 'Update')).toBe(
+      'Orca Orchestration was used. Update the orchestration skill to enable agents to coordinate reliably.'
     )
   })
 
   it('names the Linear worktree context', () => {
-    expect(getManagedSkillContextCopy('linear-worktree')).toBe(
-      'This Linear task workflow needs the Linear agent skill. Orca could not update it automatically.'
+    expect(getManagedSkillContextCopy('linear-worktree', 'Install')).toBe(
+      'A worktree was started from a Linear task. Install the Linear agent skill to enable agents to read and update Linear issues.'
     )
   })
 
+  it('splits workspace-aware context copy so the workspace can expose its full path', () => {
+    expect(getManagedSkillContextWorkspaceCopy('agent-computer-use', 'Install')).toEqual({
+      beforeWorkspace: 'Computer Use was used in ',
+      afterWorkspace: '. Install the Computer Use skill to enable agents to control apps reliably.'
+    })
+  })
+
   it('localizes fallback reason copy in the renderer', () => {
     expect(getManagedSkillFallbackDisplayMessage('remote-runtime')).toBe(
-      'Remote runtimes are not updated in the background.'
+      'This skill is on a remote runtime, so Orca needs you to update it there.'
     )
   })
 })
diff --git a/src/renderer/src/components/skills/ManagedAgentSkillSetupDialogHost.tsx b/src/renderer/src/components/skills/ManagedAgentSkillSetupDialogHost.tsx
index b23c3a065f3..5c767bb1bc5 100644
--- a/src/renderer/src/components/skills/ManagedAgentSkillSetupDialogHost.tsx
+++ b/src/renderer/src/components/skills/ManagedAgentSkillSetupDialogHost.tsx
@@ -8,6 +8,7 @@ import {
 } from '@/hooks/useInstalledAgentSkills'
 import {
   getManagedSkillContextCopy,
+  getManagedSkillContextWorkspaceCopy,
   getManagedSkillFallbackDisplayMessage
 } from './managed-agent-skill-dialog-copy'
 import {
@@ -32,6 +33,7 @@ import {
   AGENT_SKILL_CLI_PREREQUISITE_NOTICE,
   isOrcaCliAvailableOnPath
 } from '@/lib/agent-skill-cli-prerequisite'
+import { basename } from '@/lib/path'
 import { translate } from '@/i18n/i18n'
 
 const DISMISS_STORAGE_PREFIX = 'orca:managed-agent-skill-setup-dismissed:'
@@ -84,7 +86,11 @@ export function ManagedAgentSkillSetupDialogHost(): React.JSX.Element | null {
     }
   }, [enqueueFallback])
 
-  const contextCopy = active ? getManagedSkillContextCopy(active.context) : ''
+  const contextActionLabel =
+    active?.manualCommand?.kind === 'update'
+      ? translate('auto.components.skills.ManagedAgentSkillSetupDialogHost.update', 'Update')
+      : translate('auto.components.skills.ManagedAgentSkillSetupDialogHost.install', 'Install')
+  const contextCopy = active ? getManagedSkillContextCopy(active.context, contextActionLabel) : ''
   const installedCommand = useMemo(
     () => (active ? buildAgentFeatureSkillUpdateCommand(active.skillName) : ''),
     [active]
@@ -134,6 +140,12 @@ export function ManagedAgentSkillSetupDialogHost(): React.JSX.Element | null {
 
   const command = active.manualCommand?.command
   const loading = installedState.loading || rechecking
+  const workspacePath = active.request.discoveryTarget?.projectRootPath?.trim() || null
+  const workspaceName = workspacePath ? basename(workspacePath) || workspacePath : null
+  const workspaceContextCopy =
+    workspacePath && workspaceName
+      ? getManagedSkillContextWorkspaceCopy(active.context, contextActionLabel)
+      : null
 
   return (
     <Dialog
@@ -154,10 +166,22 @@ export function ManagedAgentSkillSetupDialogHost(): React.JSX.Element | null {
                 'Agent skill setup needed'
               )}
             </DialogTitle>
-            <DialogDescription>{contextCopy}</DialogDescription>
+            <DialogDescription>
+              {workspaceContextCopy && workspacePath && workspaceName ? (
+                <>
+                  {workspaceContextCopy.beforeWorkspace}
+                  <span className="font-medium text-foreground" title={workspacePath}>
+                    {workspaceName}
+                  </span>
+                  {workspaceContextCopy.afterWorkspace}
+                </>
+              ) : (
+                contextCopy
+              )}
+            </DialogDescription>
           </DialogHeader>
           <div className="mt-4 flex items-start gap-2 text-[13px] leading-snug text-muted-foreground">
-            <Info className="mt-0.5 size-4 shrink-0" />
+            <Info className="mt-px size-4 shrink-0" />
             <p>{getManagedSkillFallbackDisplayMessage(active.reason)}</p>
           </div>
         </div>
@@ -170,7 +194,6 @@ export function ManagedAgentSkillSetupDialogHost(): React.JSX.Element | null {
               'auto.components.skills.ManagedAgentSkillSetupDialogHost.panelTitle',
               'Set up managed agent skill'
             )}
-            description={contextCopy}
             command={command}
             installedCommand={installedCommand}
             terminalTitle={translate(
@@ -186,17 +209,7 @@ export function ManagedAgentSkillSetupDialogHost(): React.JSX.Element | null {
             installed={installedState.installed}
             loading={loading}
             error={installedState.error}
-            installLabel={
-              active.manualCommand?.kind === 'update'
-                ? translate(
-                    'auto.components.skills.ManagedAgentSkillSetupDialogHost.update',
-                    'Update'
-                  )
-                : translate(
-                    'auto.components.skills.ManagedAgentSkillSetupDialogHost.install',
-                    'Install'
-                  )
-            }
+            installLabel={contextActionLabel}
             installedInstallLabel={translate(
               'auto.components.skills.ManagedAgentSkillSetupDialogHost.update',
               'Update'
diff --git a/src/renderer/src/components/skills/managed-agent-skill-dialog-copy.ts b/src/renderer/src/components/skills/managed-agent-skill-dialog-copy.ts
index b7f4caf444f..8e84120cbfc 100644
--- a/src/renderer/src/components/skills/managed-agent-skill-dialog-copy.ts
+++ b/src/renderer/src/components/skills/managed-agent-skill-dialog-copy.ts
@@ -4,31 +4,99 @@ import type {
 } from '../../../../shared/skills'
 import { translate } from '@/i18n/i18n'
 
-export function getManagedSkillContextCopy(context: ManagedAgentSkillContext): string {
+export type ManagedSkillContextWorkspaceCopy = {
+  beforeWorkspace: string
+  afterWorkspace: string
+}
+
+export function getManagedSkillContextCopy(
+  context: ManagedAgentSkillContext,
+  actionLabel: string
+): string {
   switch (context) {
     case 'linear-worktree':
       return translate(
         'auto.components.skills.ManagedAgentSkillSetupDialogHost.linearWorktreeContext',
-        'This Linear task workflow needs the Linear agent skill. Orca could not update it automatically.'
+        'A worktree was started from a Linear task. {{actionLabel}} the Linear agent skill to enable agents to read and update Linear issues.',
+        { actionLabel }
       )
     case 'agent-orchestration':
       return translate(
         'auto.components.skills.ManagedAgentSkillSetupDialogHost.agentOrchestrationContext',
-        'An agent just tried to use Orca orchestration. Orca needs the orchestration skill before agents can coordinate reliably.'
+        'Orca Orchestration was used. {{actionLabel}} the orchestration skill to enable agents to coordinate reliably.',
+        { actionLabel }
       )
     case 'agent-computer-use':
       return translate(
         'auto.components.skills.ManagedAgentSkillSetupDialogHost.agentComputerUseContext',
-        'An agent just tried to use Computer Use. Orca needs the Computer Use skill before agents can control apps reliably.'
+        'Computer Use was used. {{actionLabel}} the Computer Use skill to enable agents to control apps reliably.',
+        { actionLabel }
       )
     case 'agent-orca-cli':
       return translate(
         'auto.components.skills.ManagedAgentSkillSetupDialogHost.agentOrcaCliContext',
-        "An agent just tried to use Orca's CLI skill for this workflow. Orca needs the CLI skill before this workflow can continue reliably."
+        'The Orca CLI skill was used. {{actionLabel}} the CLI skill to enable this workflow to continue reliably.',
+        { actionLabel }
       )
   }
 }
 
+export function getManagedSkillContextWorkspaceCopy(
+  context: ManagedAgentSkillContext,
+  actionLabel: string
+): ManagedSkillContextWorkspaceCopy {
+  switch (context) {
+    case 'linear-worktree':
+      return {
+        beforeWorkspace: translate(
+          'auto.components.skills.ManagedAgentSkillSetupDialogHost.linearWorktreeContextBeforeWorkspace',
+          'A worktree was started from a Linear task in '
+        ),
+        afterWorkspace: translate(
+          'auto.components.skills.ManagedAgentSkillSetupDialogHost.linearWorktreeContextAfterWorkspace',
+          '. {{actionLabel}} the Linear agent skill to enable agents to read and update Linear issues.',
+          { actionLabel }
+        )
+      }
+    case 'agent-orchestration':
+      return {
+        beforeWorkspace: translate(
+          'auto.components.skills.ManagedAgentSkillSetupDialogHost.agentOrchestrationContextBeforeWorkspace',
+          'Orca Orchestration was used in '
+        ),
+        afterWorkspace: translate(
+          'auto.components.skills.ManagedAgentSkillSetupDialogHost.agentOrchestrationContextAfterWorkspace',
+          '. {{actionLabel}} the orchestration skill to enable agents to coordinate reliably.',
+          { actionLabel }
+        )
+      }
+    case 'agent-computer-use':
+      return {
+        beforeWorkspace: translate(
+          'auto.components.skills.ManagedAgentSkillSetupDialogHost.agentComputerUseContextBeforeWorkspace',
+          'Computer Use was used in '
+        ),
+        afterWorkspace: translate(
+          'auto.components.skills.ManagedAgentSkillSetupDialogHost.agentComputerUseContextAfterWorkspace',
+          '. {{actionLabel}} the Computer Use skill to enable agents to control apps reliably.',
+          { actionLabel }
+        )
+      }
+    case 'agent-orca-cli':
+      return {
+        beforeWorkspace: translate(
+          'auto.components.skills.ManagedAgentSkillSetupDialogHost.agentOrcaCliContextBeforeWorkspace',
+          'The Orca CLI skill was used in '
+        ),
+        afterWorkspace: translate(
+          'auto.components.skills.ManagedAgentSkillSetupDialogHost.agentOrcaCliContextAfterWorkspace',
+          '. {{actionLabel}} the CLI skill to enable this workflow to continue reliably.',
+          { actionLabel }
+        )
+      }
+  }
+}
+
 export function getManagedSkillFallbackDisplayMessage(
   reason: ManagedAgentSkillFallbackReason
 ): string {
@@ -36,92 +104,92 @@ export function getManagedSkillFallbackDisplayMessage(
     case 'target-required':
       return translate(
         'auto.components.skills.ManagedAgentSkillSetupDialogHost.targetRequired',
-        'Orca could not resolve the runtime that should read this skill.'
+        "Orca couldn't tell which runtime should use this skill."
       )
     case 'unsupported-skill':
       return translate(
         'auto.components.skills.ManagedAgentSkillSetupDialogHost.unsupportedSkill',
-        'This is not an Orca-managed agent skill.'
+        "This isn't an Orca-managed skill."
       )
     case 'repair-required-runtime':
       return translate(
         'auto.components.skills.ManagedAgentSkillSetupDialogHost.repairRequiredRuntime',
-        'The selected runtime needs repair before Orca can inspect its skills.'
+        'This runtime needs repair before Orca can inspect its skills.'
       )
     case 'remote-runtime':
       return translate(
         'auto.components.skills.ManagedAgentSkillSetupDialogHost.remoteRuntime',
-        'Remote runtimes are not updated in the background.'
+        'This skill is on a remote runtime, so Orca needs you to update it there.'
       )
     case 'wsl-runtime':
       return translate(
         'auto.components.skills.ManagedAgentSkillSetupDialogHost.wslRuntime',
-        'WSL skill updates are manual in this version.'
+        'This skill is in WSL, so Orca needs you to update it there.'
       )
     case 'missing-install':
       return translate(
         'auto.components.skills.ManagedAgentSkillSetupDialogHost.missingInstall',
-        'The managed skill is not installed in the selected runtime.'
+        "This skill isn't installed for this runtime yet."
       )
     case 'project-install':
       return translate(
         'auto.components.skills.ManagedAgentSkillSetupDialogHost.projectInstall',
-        'Project-scoped skills are not updated in the background.'
+        "This skill is installed in the project, so Orca won't update it automatically."
       )
     case 'ambiguous-install':
       return translate(
         'auto.components.skills.ManagedAgentSkillSetupDialogHost.ambiguousInstall',
-        'Orca found both global and project-scoped copies of this skill.'
+        'Orca found more than one copy of this skill and needs you to choose the right one.'
       )
     case 'bundled-or-plugin-install':
       return translate(
         'auto.components.skills.ManagedAgentSkillSetupDialogHost.bundledOrPluginInstall',
-        'Bundled and plugin-cache skills are not mutated by Orca.'
+        "This skill comes from Orca or a plugin, so Orca won't modify it here."
       )
     case 'symlinked-global-install':
       return translate(
         'auto.components.skills.ManagedAgentSkillSetupDialogHost.symlinkedGlobalInstall',
-        'Symlinked global skills are not safe for background updates yet.'
+        "This global skill is symlinked, so Orca won't change it automatically."
       )
     case 'unsupported-cli-contract':
       return translate(
         'auto.components.skills.ManagedAgentSkillSetupDialogHost.unsupportedCliContract',
-        'This build does not include the verified skills CLI update contract.'
+        "This Orca build can't verify skill updates yet."
       )
     case 'expected-hash-missing':
       return translate(
         'auto.components.skills.ManagedAgentSkillSetupDialogHost.expectedHashMissing',
-        'This build does not include an expected hash for this managed skill.'
+        "This Orca build can't verify the expected version of this skill."
       )
     case 'lockfile-missing':
       return translate(
         'auto.components.skills.ManagedAgentSkillSetupDialogHost.lockfileMissing',
-        'Orca could not find the global skills lockfile.'
+        "Orca couldn't find the global skills lockfile needed to verify this update."
       )
     case 'lockfile-malformed':
       return translate(
         'auto.components.skills.ManagedAgentSkillSetupDialogHost.lockfileMalformed',
-        'The global skills lockfile could not be parsed.'
+        "Orca couldn't read the global skills lockfile needed to verify this update."
       )
     case 'lockfile-unsupported-schema':
       return translate(
         'auto.components.skills.ManagedAgentSkillSetupDialogHost.lockfileUnsupportedSchema',
-        'The global skills lockfile uses an unsupported schema version.'
+        "The global skills lockfile uses a format Orca doesn't support yet."
       )
     case 'lock-entry-missing':
       return translate(
         'auto.components.skills.ManagedAgentSkillSetupDialogHost.lockEntryMissing',
-        'The global skills lockfile does not track this skill.'
+        "The global skills lockfile doesn't track this skill, so Orca can't verify the update."
       )
     case 'lock-entry-unmanaged-source':
       return translate(
         'auto.components.skills.ManagedAgentSkillSetupDialogHost.lockEntryUnmanagedSource',
-        'The installed skill is not tracked as Orca-managed source.'
+        "This installed skill isn't tracked as Orca-managed, so Orca won't update it automatically."
       )
     case 'background-update-disabled':
       return translate(
         'auto.components.skills.ManagedAgentSkillSetupDialogHost.backgroundUpdateDisabled',
-        'Automatic skill updates are turned off, so this update needs manual review.'
+        'Automatic skill updates are off, so Orca needs you to run this update.'
       )
     case 'cooldown':
       return translate(
@@ -131,12 +199,12 @@ export function getManagedSkillFallbackDisplayMessage(
     case 'update-failed':
       return translate(
         'auto.components.skills.ManagedAgentSkillSetupDialogHost.updateFailed',
-        'The managed-skill update command failed.'
+        'Orca tried to update this skill automatically, but the command failed.'
       )
     case 'update-timeout':
       return translate(
         'auto.components.skills.ManagedAgentSkillSetupDialogHost.updateTimeout',
-        'The managed-skill update command timed out.'
+        'Orca tried to update this skill automatically, but the command timed out.'
       )
   }
 }
diff --git a/src/renderer/src/i18n/locales/en.json b/src/renderer/src/i18n/locales/en.json
index c5d470f74ae..f7b436676bb 100644
--- a/src/renderer/src/i18n/locales/en.json
+++ b/src/renderer/src/i18n/locales/en.json
@@ -153,7 +153,7 @@
             "d2e43e426a": "{{value0}} must be an object.",
             "fb290366b2": "Unavailable on web.",
             "76122208ca": "Shortcut for \"{{value0}}\" was ignored: {{value1}}",
-            "remoteManagedSkillRuntime": "Remote runtimes are not updated in the background.",
+            "remoteManagedSkillRuntime": "This skill is on a remote runtime, so Orca needs you to update it there.",
             "remoteManagedSkillCooldown": "Orca recently tried this managed-skill check and is cooling down."
           }
         },
@@ -3315,31 +3315,39 @@
           "recheck": "Re-check",
           "dontShowAgain": "Don't show again",
           "notNow": "Not now",
-          "linearWorktreeContext": "This Linear task workflow needs the Linear agent skill. Orca could not update it automatically.",
-          "agentOrchestrationContext": "An agent just tried to use Orca orchestration. Orca needs the orchestration skill before agents can coordinate reliably.",
-          "agentComputerUseContext": "An agent just tried to use Computer Use. Orca needs the Computer Use skill before agents can control apps reliably.",
-          "agentOrcaCliContext": "An agent just tried to use Orca's CLI skill for this workflow. Orca needs the CLI skill before this workflow can continue reliably.",
-          "targetRequired": "Orca could not resolve the runtime that should read this skill.",
-          "unsupportedSkill": "This is not an Orca-managed agent skill.",
-          "repairRequiredRuntime": "The selected runtime needs repair before Orca can inspect its skills.",
-          "remoteRuntime": "Remote runtimes are not updated in the background.",
-          "wslRuntime": "WSL skill updates are manual in this version.",
-          "missingInstall": "The managed skill is not installed in the selected runtime.",
-          "projectInstall": "Project-scoped skills are not updated in the background.",
-          "ambiguousInstall": "Orca found both global and project-scoped copies of this skill.",
-          "bundledOrPluginInstall": "Bundled and plugin-cache skills are not mutated by Orca.",
-          "symlinkedGlobalInstall": "Symlinked global skills are not safe for background updates yet.",
-          "unsupportedCliContract": "This build does not include the verified skills CLI update contract.",
-          "expectedHashMissing": "This build does not include an expected hash for this managed skill.",
-          "lockfileMissing": "Orca could not find the global skills lockfile.",
-          "lockfileMalformed": "The global skills lockfile could not be parsed.",
-          "lockfileUnsupportedSchema": "The global skills lockfile uses an unsupported schema version.",
-          "lockEntryMissing": "The global skills lockfile does not track this skill.",
-          "lockEntryUnmanagedSource": "The installed skill is not tracked as Orca-managed source.",
-          "backgroundUpdateDisabled": "Automatic skill updates are turned off, so this update needs manual review.",
+          "linearWorktreeContext": "A worktree was started from a Linear task. {{actionLabel}} the Linear agent skill to enable agents to read and update Linear issues.",
+          "agentOrchestrationContext": "Orca Orchestration was used. {{actionLabel}} the orchestration skill to enable agents to coordinate reliably.",
+          "agentComputerUseContext": "Computer Use was used. {{actionLabel}} the Computer Use skill to enable agents to control apps reliably.",
+          "agentOrcaCliContext": "The Orca CLI skill was used. {{actionLabel}} the CLI skill to enable this workflow to continue reliably.",
+          "linearWorktreeContextBeforeWorkspace": "A worktree was started from a Linear task in ",
+          "linearWorktreeContextAfterWorkspace": ". {{actionLabel}} the Linear agent skill to enable agents to read and update Linear issues.",
+          "agentOrchestrationContextBeforeWorkspace": "Orca Orchestration was used in ",
+          "agentOrchestrationContextAfterWorkspace": ". {{actionLabel}} the orchestration skill to enable agents to coordinate reliably.",
+          "agentComputerUseContextBeforeWorkspace": "Computer Use was used in ",
+          "agentComputerUseContextAfterWorkspace": ". {{actionLabel}} the Computer Use skill to enable agents to control apps reliably.",
+          "agentOrcaCliContextBeforeWorkspace": "The Orca CLI skill was used in ",
+          "agentOrcaCliContextAfterWorkspace": ". {{actionLabel}} the CLI skill to enable this workflow to continue reliably.",
+          "targetRequired": "Orca couldn't tell which runtime should use this skill.",
+          "unsupportedSkill": "This isn't an Orca-managed skill.",
+          "repairRequiredRuntime": "This runtime needs repair before Orca can inspect its skills.",
+          "remoteRuntime": "This skill is on a remote runtime, so Orca needs you to update it there.",
+          "wslRuntime": "This skill is in WSL, so Orca needs you to update it there.",
+          "missingInstall": "This skill isn't installed for this runtime yet.",
+          "projectInstall": "This skill is installed in the project, so Orca won't update it automatically.",
+          "ambiguousInstall": "Orca found more than one copy of this skill and needs you to choose the right one.",
+          "bundledOrPluginInstall": "This skill comes from Orca or a plugin, so Orca won't modify it here.",
+          "symlinkedGlobalInstall": "This global skill is symlinked, so Orca won't change it automatically.",
+          "unsupportedCliContract": "This Orca build can't verify skill updates yet.",
+          "expectedHashMissing": "This Orca build can't verify the expected version of this skill.",
+          "lockfileMissing": "Orca couldn't find the global skills lockfile needed to verify this update.",
+          "lockfileMalformed": "Orca couldn't read the global skills lockfile needed to verify this update.",
+          "lockfileUnsupportedSchema": "The global skills lockfile uses a format Orca doesn't support yet.",
+          "lockEntryMissing": "The global skills lockfile doesn't track this skill, so Orca can't verify the update.",
+          "lockEntryUnmanagedSource": "This installed skill isn't tracked as Orca-managed, so Orca won't update it automatically.",
+          "backgroundUpdateDisabled": "Automatic skill updates are off, so Orca needs you to run this update.",
           "cooldown": "Orca recently tried this managed-skill check and is cooling down.",
-          "updateFailed": "The managed-skill update command failed.",
-          "updateTimeout": "The managed-skill update command timed out."
+          "updateFailed": "Orca tried to update this skill automatically, but the command failed.",
+          "updateTimeout": "Orca tried to update this skill automatically, but the command timed out."
         }
       },
       "sidebar": {
diff --git a/src/renderer/src/i18n/locales/es.json b/src/renderer/src/i18n/locales/es.json
index 1f7ecd1d99a..d686c1262ae 100644
--- a/src/renderer/src/i18n/locales/es.json
+++ b/src/renderer/src/i18n/locales/es.json
@@ -3315,10 +3315,10 @@
           "recheck": "Volver a comprobar",
           "dontShowAgain": "No volver a mostrar",
           "notNow": "Ahora no",
-          "linearWorktreeContext": "Este flujo de tarea de Linear necesita la habilidad de agente de Linear. Orca no pudo actualizarla automáticamente.",
-          "agentOrchestrationContext": "Un agente acaba de intentar usar la orquestación de Orca. Orca necesita la habilidad de orquestación para que los agentes puedan coordinarse de forma fiable.",
-          "agentComputerUseContext": "Un agente acaba de intentar usar Computer Use. Orca necesita la habilidad Computer Use para que los agentes puedan controlar apps de forma fiable.",
-          "agentOrcaCliContext": "Un agente acaba de intentar usar la habilidad de CLI de Orca para este flujo. Orca necesita la habilidad de CLI para que este flujo pueda continuar de forma fiable.",
+          "linearWorktreeContext": "A worktree was started from a Linear task. {{actionLabel}} the Linear agent skill to enable agents to read and update Linear issues.",
+          "agentOrchestrationContext": "Orca Orchestration was used. {{actionLabel}} the orchestration skill to enable agents to coordinate reliably.",
+          "agentComputerUseContext": "Computer Use was used. {{actionLabel}} the Computer Use skill to enable agents to control apps reliably.",
+          "agentOrcaCliContext": "The Orca CLI skill was used. {{actionLabel}} the CLI skill to enable this workflow to continue reliably.",
           "targetRequired": "Orca no pudo resolver el entorno de ejecución que debe leer esta habilidad.",
           "unsupportedSkill": "Esta no es una habilidad de agente administrada por Orca.",
           "repairRequiredRuntime": "El entorno de ejecución seleccionado necesita reparación antes de que Orca pueda inspeccionar sus habilidades.",
@@ -3339,7 +3339,15 @@
           "backgroundUpdateDisabled": "Las actualizaciones automáticas de habilidades están desactivadas, por lo que esta actualización necesita revisión manual.",
           "cooldown": "Orca intentó recientemente esta comprobación de habilidad administrada y está esperando antes de volver a intentarlo.",
           "updateFailed": "El comando de actualización de la habilidad administrada falló.",
-          "updateTimeout": "El comando de actualización de la habilidad administrada agotó el tiempo de espera."
+          "updateTimeout": "El comando de actualización de la habilidad administrada agotó el tiempo de espera.",
+          "linearWorktreeContextBeforeWorkspace": "A worktree was started from a Linear task in ",
+          "linearWorktreeContextAfterWorkspace": ". {{actionLabel}} the Linear agent skill to enable agents to read and update Linear issues.",
+          "agentOrchestrationContextBeforeWorkspace": "Orca Orchestration was used in ",
+          "agentOrchestrationContextAfterWorkspace": ". {{actionLabel}} the orchestration skill to enable agents to coordinate reliably.",
+          "agentComputerUseContextBeforeWorkspace": "Computer Use was used in ",
+          "agentComputerUseContextAfterWorkspace": ". {{actionLabel}} the Computer Use skill to enable agents to control apps reliably.",
+          "agentOrcaCliContextBeforeWorkspace": "The Orca CLI skill was used in ",
+          "agentOrcaCliContextAfterWorkspace": ". {{actionLabel}} the CLI skill to enable this workflow to continue reliably."
         }
       },
       "sidebar": {
diff --git a/src/renderer/src/i18n/locales/ja.json b/src/renderer/src/i18n/locales/ja.json
index 8499ddd598f..f461251fc21 100644
--- a/src/renderer/src/i18n/locales/ja.json
+++ b/src/renderer/src/i18n/locales/ja.json
@@ -3315,10 +3315,10 @@
           "recheck": "再チェック",
           "dontShowAgain": "今後表示しない",
           "notNow": "今はしない",
-          "linearWorktreeContext": "この Linear タスクのワークフローには Linear エージェントスキルが必要です。Orca は自動更新できませんでした。",
-          "agentOrchestrationContext": "エージェントが Orca オーケストレーションを使おうとしました。エージェントが確実に連携するには、Orca にオーケストレーションスキルが必要です。",
-          "agentComputerUseContext": "エージェントが Computer Use を使おうとしました。エージェントがアプリを確実に操作するには、Orca に Computer Use スキルが必要です。",
-          "agentOrcaCliContext": "エージェントがこのワークフローで Orca の CLI スキルを使おうとしました。このワークフローを確実に続行するには、Orca に CLI スキルが必要です。",
+          "linearWorktreeContext": "A worktree was started from a Linear task. {{actionLabel}} the Linear agent skill to enable agents to read and update Linear issues.",
+          "agentOrchestrationContext": "Orca Orchestration was used. {{actionLabel}} the orchestration skill to enable agents to coordinate reliably.",
+          "agentComputerUseContext": "Computer Use was used. {{actionLabel}} the Computer Use skill to enable agents to control apps reliably.",
+          "agentOrcaCliContext": "The Orca CLI skill was used. {{actionLabel}} the CLI skill to enable this workflow to continue reliably.",
           "targetRequired": "Orca はこのスキルを読み取るランタイムを解決できませんでした。",
           "unsupportedSkill": "これは Orca 管理のエージェントスキルではありません。",
           "repairRequiredRuntime": "Orca がスキルを検査する前に、選択したランタイムの修復が必要です。",
@@ -3339,7 +3339,15 @@
           "backgroundUpdateDisabled": "スキルの自動更新がオフになっているため、この更新には手動確認が必要です。",
           "cooldown": "Orca は最近この管理対象スキルのチェックを試行したため、クールダウン中です。",
           "updateFailed": "管理対象スキルの更新コマンドに失敗しました。",
-          "updateTimeout": "管理対象スキルの更新コマンドがタイムアウトしました。"
+          "updateTimeout": "管理対象スキルの更新コマンドがタイムアウトしました。",
+          "linearWorktreeContextBeforeWorkspace": "A worktree was started from a Linear task in ",
+          "linearWorktreeContextAfterWorkspace": ". {{actionLabel}} the Linear agent skill to enable agents to read and update Linear issues.",
+          "agentOrchestrationContextBeforeWorkspace": "Orca Orchestration was used in ",
+          "agentOrchestrationContextAfterWorkspace": ". {{actionLabel}} the orchestration skill to enable agents to coordinate reliably.",
+          "agentComputerUseContextBeforeWorkspace": "Computer Use was used in ",
+          "agentComputerUseContextAfterWorkspace": ". {{actionLabel}} the Computer Use skill to enable agents to control apps reliably.",
+          "agentOrcaCliContextBeforeWorkspace": "The Orca CLI skill was used in ",
+          "agentOrcaCliContextAfterWorkspace": ". {{actionLabel}} the CLI skill to enable this workflow to continue reliably."
         }
       },
       "sidebar": {
diff --git a/src/renderer/src/i18n/locales/ko.json b/src/renderer/src/i18n/locales/ko.json
index 39ac2499aeb..2b9d6860a3b 100644
--- a/src/renderer/src/i18n/locales/ko.json
+++ b/src/renderer/src/i18n/locales/ko.json
@@ -3315,10 +3315,10 @@
           "recheck": "다시 확인",
           "dontShowAgain": "다시 표시하지 않기",
           "notNow": "나중에",
-          "linearWorktreeContext": "이 Linear 작업 흐름에는 Linear 에이전트 스킬이 필요합니다. Orca가 자동으로 업데이트할 수 없습니다.",
-          "agentOrchestrationContext": "에이전트가 방금 Orca 오케스트레이션을 사용하려고 했습니다. 에이전트가 안정적으로 조율되려면 Orca에 오케스트레이션 스킬이 필요합니다.",
-          "agentComputerUseContext": "에이전트가 방금 Computer Use를 사용하려고 했습니다. 에이전트가 앱을 안정적으로 제어하려면 Orca에 Computer Use 스킬이 필요합니다.",
-          "agentOrcaCliContext": "에이전트가 이 흐름에서 Orca의 CLI 스킬을 사용하려고 했습니다. 이 흐름을 안정적으로 계속하려면 Orca에 CLI 스킬이 필요합니다.",
+          "linearWorktreeContext": "A worktree was started from a Linear task. {{actionLabel}} the Linear agent skill to enable agents to read and update Linear issues.",
+          "agentOrchestrationContext": "Orca Orchestration was used. {{actionLabel}} the orchestration skill to enable agents to coordinate reliably.",
+          "agentComputerUseContext": "Computer Use was used. {{actionLabel}} the Computer Use skill to enable agents to control apps reliably.",
+          "agentOrcaCliContext": "The Orca CLI skill was used. {{actionLabel}} the CLI skill to enable this workflow to continue reliably.",
           "targetRequired": "Orca가 이 스킬을 읽어야 하는 런타임을 확인할 수 없습니다.",
           "unsupportedSkill": "Orca가 관리하는 에이전트 스킬이 아닙니다.",
           "repairRequiredRuntime": "Orca가 스킬을 검사하기 전에 선택한 런타임을 복구해야 합니다.",
@@ -3339,7 +3339,15 @@
           "backgroundUpdateDisabled": "자동 스킬 업데이트가 꺼져 있어 이 업데이트는 수동 검토가 필요합니다.",
           "cooldown": "Orca가 최근 이 관리형 스킬 확인을 시도했으며 현재 대기 중입니다.",
           "updateFailed": "관리형 스킬 업데이트 명령이 실패했습니다.",
-          "updateTimeout": "관리형 스킬 업데이트 명령 시간이 초과되었습니다."
+          "updateTimeout": "관리형 스킬 업데이트 명령 시간이 초과되었습니다.",
+          "linearWorktreeContextBeforeWorkspace": "A worktree was started from a Linear task in ",
+          "linearWorktreeContextAfterWorkspace": ". {{actionLabel}} the Linear agent skill to enable agents to read and update Linear issues.",
+          "agentOrchestrationContextBeforeWorkspace": "Orca Orchestration was used in ",
+          "agentOrchestrationContextAfterWorkspace": ". {{actionLabel}} the orchestration skill to enable agents to coordinate reliably.",
+          "agentComputerUseContextBeforeWorkspace": "Computer Use was used in ",
+          "agentComputerUseContextAfterWorkspace": ". {{actionLabel}} the Computer Use skill to enable agents to control apps reliably.",
+          "agentOrcaCliContextBeforeWorkspace": "The Orca CLI skill was used in ",
+          "agentOrcaCliContextAfterWorkspace": ". {{actionLabel}} the CLI skill to enable this workflow to continue reliably."
         }
       },
       "sidebar": {
diff --git a/src/renderer/src/i18n/locales/zh.json b/src/renderer/src/i18n/locales/zh.json
index f23031056bb..4ad1597209b 100644
--- a/src/renderer/src/i18n/locales/zh.json
+++ b/src/renderer/src/i18n/locales/zh.json
@@ -3315,10 +3315,10 @@
           "recheck": "重新检查",
           "dontShowAgain": "不再显示",
           "notNow": "稍后",
-          "linearWorktreeContext": "此 Linear 任务流程需要 Linear 代理技能。Orca 无法自动更新它。",
-          "agentOrchestrationContext": "代理刚刚尝试使用 Orca 编排。Orca 需要编排技能，代理才能可靠地协作。",
-          "agentComputerUseContext": "代理刚刚尝试使用 Computer Use。Orca 需要 Computer Use 技能，代理才能可靠地控制应用。",
-          "agentOrcaCliContext": "代理刚刚尝试在此流程中使用 Orca 的 CLI 技能。Orca 需要 CLI 技能，此流程才能可靠地继续。",
+          "linearWorktreeContext": "A worktree was started from a Linear task. {{actionLabel}} the Linear agent skill to enable agents to read and update Linear issues.",
+          "agentOrchestrationContext": "Orca Orchestration was used. {{actionLabel}} the orchestration skill to enable agents to coordinate reliably.",
+          "agentComputerUseContext": "Computer Use was used. {{actionLabel}} the Computer Use skill to enable agents to control apps reliably.",
+          "agentOrcaCliContext": "The Orca CLI skill was used. {{actionLabel}} the CLI skill to enable this workflow to continue reliably.",
           "targetRequired": "Orca 无法解析应读取此技能的运行时。",
           "unsupportedSkill": "这不是 Orca 托管的代理技能。",
           "repairRequiredRuntime": "所选运行时需要修复，Orca 才能检查其技能。",
@@ -3339,7 +3339,15 @@
           "backgroundUpdateDisabled": "自动技能更新已关闭，因此此次更新需要手动审核。",
           "cooldown": "Orca 最近已尝试此托管技能检查，正在等待重试。",
           "updateFailed": "托管技能更新命令失败。",
-          "updateTimeout": "托管技能更新命令超时。"
+          "updateTimeout": "托管技能更新命令超时。",
+          "linearWorktreeContextBeforeWorkspace": "A worktree was started from a Linear task in ",
+          "linearWorktreeContextAfterWorkspace": ". {{actionLabel}} the Linear agent skill to enable agents to read and update Linear issues.",
+          "agentOrchestrationContextBeforeWorkspace": "Orca Orchestration was used in ",
+          "agentOrchestrationContextAfterWorkspace": ". {{actionLabel}} the orchestration skill to enable agents to coordinate reliably.",
+          "agentComputerUseContextBeforeWorkspace": "Computer Use was used in ",
+          "agentComputerUseContextAfterWorkspace": ". {{actionLabel}} the Computer Use skill to enable agents to control apps reliably.",
+          "agentOrcaCliContextBeforeWorkspace": "The Orca CLI skill was used in ",
+          "agentOrcaCliContextAfterWorkspace": ". {{actionLabel}} the CLI skill to enable this workflow to continue reliably."
         }
       },
       "sidebar": {
diff --git a/src/renderer/src/store/slices/worktrees.test.ts b/src/renderer/src/store/slices/worktrees.test.ts
index dca09347e21..770bcd65909 100644
--- a/src/renderer/src/store/slices/worktrees.test.ts
+++ b/src/renderer/src/store/slices/worktrees.test.ts
@@ -90,7 +90,7 @@ const mockApi = {
       scope: 'missing',
       reason: 'remote-runtime',
       uiKey: 'remote::linear-tickets:linear-worktree',
-      message: 'Remote runtimes are not updated in the background.',
+      message: 'This skill is on a remote runtime, so Orca needs you to update it there.',
       request: {
         skillName: 'linear-tickets',
         context: 'linear-worktree',
diff --git a/src/renderer/src/web/web-preload-api.ts b/src/renderer/src/web/web-preload-api.ts
index bcd7c94648e..c9ffb86ed77 100644
--- a/src/renderer/src/web/web-preload-api.ts
+++ b/src/renderer/src/web/web-preload-api.ts
@@ -2341,7 +2341,7 @@ function createSkillsApi(): NonNullable<Partial<PreloadApi>['skills']> {
         uiKey,
         message: translate(
           'auto.web.web.preload.api.remoteManagedSkillRuntime',
-          'Remote runtimes are not updated in the background.'
+          'This skill is on a remote runtime, so Orca needs you to update it there.'
         ),
         request
       } satisfies ManagedAgentSkillFallback