diff --git a/orchestrator/src/client/components/CoverLetterDisplay.tsx b/orchestrator/src/client/components/CoverLetterDisplay.tsx
index 72fc9e6..959f5a7 100644
--- a/orchestrator/src/client/components/CoverLetterDisplay.tsx
+++ b/orchestrator/src/client/components/CoverLetterDisplay.tsx
@@ -1,17 +1,23 @@
 import type { Job } from "@shared/types.js";
-import { Check, Copy, FileText } from "lucide-react";
+import { Check, Copy, FileText, Loader2, RefreshCw } from "lucide-react";
 import type React from "react";
 import { useCallback, useState } from "react";
+import { Button } from "@/components/ui/button";
 import { cn } from "@/lib/utils";
 
 interface CoverLetterDisplayProps {
   job: Job;
   className?: string;
+  /** When set, shows Generate (no letter) or Regenerate (has letter) instead of hiding entirely. */
+  onRequestGenerate?: () => void | Promise<void>;
+  generateInFlight?: boolean;
 }
 
 export const CoverLetterDisplay: React.FC<CoverLetterDisplayProps> = ({
   job,
   className,
+  onRequestGenerate,
+  generateInFlight = false,
 }) => {
   const [copied, setCopied] = useState(false);
   const [expanded, setExpanded] = useState(false);
@@ -23,7 +29,54 @@ export const CoverLetterDisplay: React.FC<CoverLetterDisplayProps> = ({
     setTimeout(() => setCopied(false), 2000);
   }, [job.coverLetter]);
 
-  if (!job.coverLetter) return null;
+  const canRunGenerate =
+    Boolean(onRequestGenerate) && job.status !== "processing";
+  const showEmptyState = !job.coverLetter && onRequestGenerate;
+
+  if (!job.coverLetter && !onRequestGenerate) {
+    return null;
+  }
+
+  if (showEmptyState) {
+    return (
+      <div className={cn("space-y-1", className)}>
+        <div className="rounded-lg border border-violet-500/20 bg-violet-500/5 px-3 py-2.5">
+          <div className="text-[11px] font-medium uppercase tracking-wide text-violet-600/80 dark:text-violet-400/80 flex items-center gap-1.5 mb-1.5">
+            <FileText className="h-3 w-3" />
+            Cover letter
+          </div>
+          <p className="text-xs text-muted-foreground leading-relaxed mb-2">
+            Saved on this job after you generate it (Overview here, or Ready
+            tab). Use Copy to paste into the employer&apos;s application form.
+          </p>
+          <Button
+            type="button"
+            size="sm"
+            variant="secondary"
+            className="h-8 text-xs"
+            disabled={!canRunGenerate || generateInFlight}
+            onClick={() => void onRequestGenerate?.()}
+          >
+            {generateInFlight ? (
+              <>
+                <Loader2 className="h-3.5 w-3.5 animate-spin mr-1.5" />
+                Generating…
+              </>
+            ) : (
+              <>
+                <FileText className="h-3.5 w-3.5 mr-1.5" />
+                Generate cover letter
+              </>
+            )}
+          </Button>
+        </div>
+      </div>
+    );
+  }
+
+  if (!job.coverLetter) {
+    return null;
+  }
 
   const lines = job.coverLetter.split("\n");
   const isLong = lines.length > 8;
@@ -32,26 +85,43 @@ export const CoverLetterDisplay: React.FC<CoverLetterDisplayProps> = ({
   return (
     <div className={cn("space-y-1", className)}>
       <div className="rounded-lg border border-violet-500/20 bg-violet-500/5 px-3 py-2.5">
-        <div className="flex items-center justify-between mb-1.5">
+        <div className="flex items-center justify-between mb-1.5 gap-2 flex-wrap">
           <div className="text-[11px] font-medium uppercase tracking-wide text-violet-600/80 dark:text-violet-400/80 flex items-center gap-1.5">
             <FileText className="h-3 w-3" />
-            Cover Letter
+            Cover letter
           </div>
-          <button
-            type="button"
-            onClick={handleCopy}
-            className="text-[10px] text-muted-foreground hover:text-foreground flex items-center gap-1 transition-colors"
-          >
-            {copied ? (
-              <>
-                <Check className="h-3 w-3" /> Copied
-              </>
-            ) : (
-              <>
-                <Copy className="h-3 w-3" /> Copy
-              </>
+          <div className="flex items-center gap-2">
+            {onRequestGenerate && (
+              <button
+                type="button"
+                onClick={() => void onRequestGenerate()}
+                disabled={!canRunGenerate || generateInFlight}
+                className="text-[10px] text-muted-foreground hover:text-foreground flex items-center gap-1 transition-colors disabled:opacity-50"
+              >
+                {generateInFlight ? (
+                  <Loader2 className="h-3 w-3 animate-spin" />
+                ) : (
+                  <RefreshCw className="h-3 w-3" />
+                )}
+                Regenerate
+              </button>
             )}
-          </button>
+            <button
+              type="button"
+              onClick={handleCopy}
+              className="text-[10px] text-muted-foreground hover:text-foreground flex items-center gap-1 transition-colors"
+            >
+              {copied ? (
+                <>
+                  <Check className="h-3 w-3" /> Copied
+                </>
+              ) : (
+                <>
+                  <Copy className="h-3 w-3" /> Copy
+                </>
+              )}
+            </button>
+          </div>
         </div>
         <p className="text-xs text-foreground/85 leading-relaxed whitespace-pre-wrap">
           {displayText}
diff --git a/orchestrator/src/client/components/ReadyPanel.tsx b/orchestrator/src/client/components/ReadyPanel.tsx
index 030fe8d..1cd35b3 100644
--- a/orchestrator/src/client/components/ReadyPanel.tsx
+++ b/orchestrator/src/client/components/ReadyPanel.tsx
@@ -45,9 +45,11 @@ import {
   useMarkAsAppliedMutation,
   useSkipJobMutation,
 } from "../hooks/queries/useJobMutations";
+import { useCoverLetterGeneration } from "../hooks/useCoverLetterGeneration";
 import { useProfile } from "../hooks/useProfile";
 import { useRescoreJob } from "../hooks/useRescoreJob";
 import { FitAssessment, JobHeader, TailoredSummary } from ".";
+import { CoverLetterDisplay } from "./CoverLetterDisplay";
 import { TailorMode } from "./discovered-panel/TailorMode";
 import { GhostwriterDrawer } from "./ghostwriter/GhostwriterDrawer";
 import { JobDetailsEditDrawer } from "./JobDetailsEditDrawer";
@@ -86,6 +88,8 @@ export const ReadyPanel: React.FC<ReadyPanelProps> = ({
   const previousJobIdRef = useRef<string | null>(null);
   const markAsAppliedMutation = useMarkAsAppliedMutation();
   const skipJobMutation = useSkipJobMutation();
+  const { generateForJob, inFlight: coverLetterGenerating } =
+    useCoverLetterGeneration(onJobUpdated);
 
   const { personName } = useProfile();
 
@@ -425,6 +429,11 @@ export const ReadyPanel: React.FC<ReadyPanelProps> = ({
       <div className="flex-1 py-4 space-y-4">
         <div className="space-y-3">
           <FitAssessment job={job} />
+          <CoverLetterDisplay
+            job={job}
+            onRequestGenerate={() => generateForJob(job.id)}
+            generateInFlight={coverLetterGenerating}
+          />
           <TailoredSummary job={job} />
 
           {googleDorks.length > 0 ? (
diff --git a/orchestrator/src/client/hooks/useCoverLetterGeneration.ts b/orchestrator/src/client/hooks/useCoverLetterGeneration.ts
new file mode 100644
index 0000000..5bd4c62
--- /dev/null
+++ b/orchestrator/src/client/hooks/useCoverLetterGeneration.ts
@@ -0,0 +1,37 @@
+import * as api from "@client/api";
+import { useCallback, useState } from "react";
+import { toast } from "sonner";
+
+export function useCoverLetterGeneration(
+  onJobUpdated: () => void | Promise<void>,
+) {
+  const [inFlight, setInFlight] = useState(false);
+
+  const generateForJob = useCallback(
+    async (jobId: string) => {
+      setInFlight(true);
+      try {
+        const res = await api.runJobAction({
+          action: "generate_cover_letter",
+          jobIds: [jobId],
+        });
+        const r = res.results.find((entry) => entry.jobId === jobId);
+        if (!r?.ok) {
+          toast.error(r?.error.message ?? "Could not generate cover letter");
+          return;
+        }
+        toast.success("Cover letter saved on this job");
+        await onJobUpdated();
+      } catch (e) {
+        toast.error(
+          e instanceof Error ? e.message : "Could not generate cover letter",
+        );
+      } finally {
+        setInFlight(false);
+      }
+    },
+    [onJobUpdated],
+  );
+
+  return { generateForJob, inFlight };
+}
diff --git a/orchestrator/src/client/pages/orchestrator/FloatingJobActionsBar.tsx b/orchestrator/src/client/pages/orchestrator/FloatingJobActionsBar.tsx
index 7e72e80..c48031c 100644
--- a/orchestrator/src/client/pages/orchestrator/FloatingJobActionsBar.tsx
+++ b/orchestrator/src/client/pages/orchestrator/FloatingJobActionsBar.tsx
@@ -88,6 +88,7 @@ export const FloatingJobActionsBar: React.FC<FloatingJobActionsBarProps> = ({
                   className="w-full sm:w-auto"
                   disabled={jobActionInFlight}
                   onClick={onGenerateCoverLetter}
+                  title="Generates for all selected jobs. You can also open one job → Overview (or Ready tab) → Cover letter."
                 >
                   Cover letter
                 </Button>
diff --git a/orchestrator/src/client/pages/orchestrator/JobDetailPanel.tsx b/orchestrator/src/client/pages/orchestrator/JobDetailPanel.tsx
index 2b11df7..049cb77 100644
--- a/orchestrator/src/client/pages/orchestrator/JobDetailPanel.tsx
+++ b/orchestrator/src/client/pages/orchestrator/JobDetailPanel.tsx
@@ -13,6 +13,7 @@ import {
   useMarkAsAppliedMutation,
   useSkipJobMutation,
 } from "@client/hooks/queries/useJobMutations";
+import { useCoverLetterGeneration } from "@client/hooks/useCoverLetterGeneration";
 import { useProfile } from "@client/hooks/useProfile";
 import { useSettings } from "@client/hooks/useSettings";
 import type { Job, JobListItem } from "@shared/types.js";
@@ -81,6 +82,8 @@ export const JobDetailPanel: React.FC<JobDetailPanelProps> = ({
   const previousSelectedJobIdRef = useRef<string | null>(null);
   const markAsAppliedMutation = useMarkAsAppliedMutation();
   const skipJobMutation = useSkipJobMutation();
+  const { generateForJob, inFlight: coverLetterGenerating } =
+    useCoverLetterGeneration(onJobUpdated);
 
   const { personName } = useProfile();
   const { renderMarkdownInJobDescriptions } = useSettings();
@@ -540,6 +543,19 @@ export const JobDetailPanel: React.FC<JobDetailPanelProps> = ({
               <Edit2 className="mr-2 h-4 w-4" />
               Edit details
             </DropdownMenuItem>
+            <DropdownMenuItem
+              onSelect={() => void generateForJob(selectedJob.id)}
+              disabled={
+                selectedJob.status === "processing" || coverLetterGenerating
+              }
+            >
+              <FileText className="mr-2 h-4 w-4" />
+              {coverLetterGenerating
+                ? "Cover letter…"
+                : selectedJob.coverLetter
+                  ? "Regenerate cover letter"
+                  : "Generate cover letter"}
+            </DropdownMenuItem>
             <DropdownMenuItem onSelect={() => void handleCopyInfo()}>
               <Copy className="mr-2 h-4 w-4" />
               Copy info
@@ -602,7 +618,11 @@ export const JobDetailPanel: React.FC<JobDetailPanelProps> = ({
 
         <TabsContent value="overview" className="space-y-3 pt-2">
           <FitAssessment job={selectedJob} />
-          <CoverLetterDisplay job={selectedJob} />
+          <CoverLetterDisplay
+            job={selectedJob}
+            onRequestGenerate={() => generateForJob(selectedJob.id)}
+            generateInFlight={coverLetterGenerating}
+          />
           <TailoredSummary job={selectedJob} />
 
           <div className="grid gap-2 text-xs sm:grid-cols-2">