diff --git a/app/(main)/configurations/prompt-editor/page.tsx b/app/(main)/configurations/prompt-editor/page.tsx
index 6c76e103..b867881d 100644
--- a/app/(main)/configurations/prompt-editor/page.tsx
+++ b/app/(main)/configurations/prompt-editor/page.tsx
@@ -23,6 +23,7 @@ import { useConfigPersistence } from "@/app/hooks/useConfigPersistence";
 import { SavedConfig, ConfigVersionItems } from "@/app/lib/types/configs";
 import { configState } from "@/app/lib/store/config";
 import { DEFAULT_CONFIG } from "@/app/lib/constants";
+import { apiFetch } from "@/app/lib/apiClient";
 
 function PromptEditorContent() {
   const searchParams = useSearchParams();
@@ -126,6 +127,29 @@ function PromptEditorContent() {
     [],
   );
 
+  const refreshVersionsForConfig = React.useCallback(
+    async (configId: string) => {
+      if (!configId) return;
+      try {
+        const apiKey = activeKey?.key ?? "";
+        const res = await apiFetch<{
+          success: boolean;
+          data: ConfigVersionItems[];
+        }>(`/api/configs/${configId}/versions`, apiKey);
+        if (res.success && res.data) {
+          configState.versionItemsCache[configId] = res.data;
+          setStableVersionItemsMap((prev) => ({
+            ...prev,
+            [configId]: res.data,
+          }));
+        }
+      } catch (err) {
+        console.error("Failed to refresh version list:", err);
+      }
+    },
+    [activeKey],
+  );
+
   const resetEditor = React.useCallback(() => {
     setCurrentContent("");
     setCurrentConfigBlob(DEFAULT_CONFIG);
@@ -247,7 +271,11 @@ function PromptEditorContent() {
     if (ok) {
       setHasUnsavedChanges(false);
       setCommitMessage("");
-      if (wasNewConfig) resetEditor();
+      if (wasNewConfig) {
+        resetEditor();
+      } else if (currentConfigParentId) {
+        await refreshVersionsForConfig(currentConfigParentId);
+      }
     }
   };
 
diff --git a/app/(main)/evaluations/[id]/page.tsx b/app/(main)/evaluations/[id]/page.tsx
index 045eda53..f4f4f27b 100644
--- a/app/(main)/evaluations/[id]/page.tsx
+++ b/app/(main)/evaluations/[id]/page.tsx
@@ -8,6 +8,7 @@
 import { useState, useEffect, useCallback, useRef } from "react";
 import { useRouter, useParams } from "next/navigation";
 import { apiFetch } from "@/app/lib/apiClient";
+import { invalidateConfigCache } from "@/app/lib/utils";
 import { useAuth } from "@/app/lib/context/AuthContext";
 import { useApp } from "@/app/lib/context/AppContext";
 import type {
@@ -70,6 +71,7 @@ export default function EvaluationReport() {
   const [isConfigModalOpen, setIsConfigModalOpen] = useState(false);
   const [exportFormat, setExportFormat] = useState<"row" | "grouped">("row");
   const [isResyncing, setIsResyncing] = useState(false);
+  const [isImprovingPrompt, setIsImprovingPrompt] = useState(false);
   const [showNoTracesModal, setShowNoTracesModal] = useState(false);
 
   const fetchJobDetails = useCallback(async () => {
@@ -180,6 +182,51 @@ export default function EvaluationReport() {
     }
   };
 
+  const handleIteratePrompt = async () => {
+    if (!isAuthenticated || !jobId) return;
+    setIsImprovingPrompt(true);
+    try {
+      const data = await apiFetch<{
+        success: boolean;
+        error?: string;
+        data?: {
+          config_id?: string;
+          id?: string;
+          version?: number;
+        } | null;
+      }>(`/api/evaluations/${jobId}/improve-prompt`, apiKey, {
+        method: "POST",
+        body: JSON.stringify({}),
+      });
+
+      if (!data.success) {
+        toast.error(data.error || "Failed to iterate on prompt");
+        return;
+      }
+
+      invalidateConfigCache();
+      toast.success("Prompt iteration created");
+
+      const newConfigId = data.data?.config_id ?? data.data?.id;
+      const newVersion = data.data?.version;
+      if (newConfigId) {
+        const versionParam =
+          typeof newVersion === "number" ? `&version=${newVersion}` : "";
+        router.push(
+          `/configurations/prompt-editor?config=${encodeURIComponent(
+            newConfigId,
+          )}${versionParam}&from=evaluations`,
+        );
+      }
+    } catch (err: unknown) {
+      toast.error(
+        `Failed to iterate on prompt: ${err instanceof Error ? err.message : "Unknown error"}`,
+      );
+    } finally {
+      setIsImprovingPrompt(false);
+    }
+  };
+
   const handleResync = async () => {
     if (!isAuthenticated || !jobId) return;
 
@@ -344,6 +391,30 @@ export default function EvaluationReport() {
                 <span className="hidden sm:inline">View Config</span>
                 <span className="sm:hidden">Config</span>
               </Button>
+              <Button
+                variant="outline"
+                size="sm"
+                onClick={handleIteratePrompt}
+                disabled={
+                  job.status.toLowerCase() !== "completed" ||
+                  isImprovingPrompt ||
+                  isFormatSwitching ||
+                  isResyncing
+                }
+                title={
+                  job.status.toLowerCase() !== "completed"
+                    ? "Only available for completed evaluations"
+                    : undefined
+                }
+              >
+                {isImprovingPrompt && <Loader size="sm" />}
+                <span className="hidden sm:inline">
+                  {isImprovingPrompt ? "Iterating..." : "Iterate on Prompt"}
+                </span>
+                <span className="sm:hidden">
+                  {isImprovingPrompt ? "..." : "Iterate"}
+                </span>
+              </Button>
               <Button
                 variant="primary"
                 size="sm"
diff --git a/app/api/evaluations/[id]/improve-prompt/route.ts b/app/api/evaluations/[id]/improve-prompt/route.ts
new file mode 100644
index 00000000..33682409
--- /dev/null
+++ b/app/api/evaluations/[id]/improve-prompt/route.ts
@@ -0,0 +1,39 @@
+import { NextRequest, NextResponse } from "next/server";
+import { apiClient } from "@/app/lib/apiClient";
+
+export async function POST(
+  request: NextRequest,
+  { params }: { params: Promise<{ id: string }> },
+) {
+  try {
+    const { id } = await params;
+
+    let body: unknown = undefined;
+    try {
+      body = await request.json();
+    } catch {
+      body = {};
+    }
+
+    const { status, data } = await apiClient(
+      request,
+      `/api/v1/evaluations/${id}/improve-prompt`,
+      {
+        method: "POST",
+        body: JSON.stringify(body ?? {}),
+      },
+    );
+
+    return NextResponse.json(data ?? { error: "Backend error" }, { status });
+  } catch (error: unknown) {
+    console.error("improve-prompt proxy error:", error);
+    return NextResponse.json(
+      {
+        success: false,
+        error:
+          error instanceof Error ? error.message : "Failed to improve prompt",
+      },
+      { status: 500 },
+    );
+  }
+}
diff --git a/app/components/CommitMessage.tsx b/app/components/CommitMessage.tsx
new file mode 100644
index 00000000..ce6a8009
--- /dev/null
+++ b/app/components/CommitMessage.tsx
@@ -0,0 +1,65 @@
+import type { CommitMessageProps, ParsedCommit } from "@/app/lib/types/commit";
+
+const AI_GENERATED_PATTERN =
+  /^\[AI Generated\]\s*(?:improved from config version\s+v(\d+))?\s*(?:\(Evaluation:\s*([^)]+)\))?\s*(.*)$/i;
+
+export function parseCommitMessage(
+  message: string | null | undefined,
+): ParsedCommit {
+  if (!message) return { isAIGenerated: false, body: "" };
+  const match = message.match(AI_GENERATED_PATTERN);
+  if (!match) return { isAIGenerated: false, body: message };
+  const [, fromVersionRaw, evalName, body] = match;
+  return {
+    isAIGenerated: true,
+    fromVersion: fromVersionRaw ? parseInt(fromVersionRaw, 10) : undefined,
+    evaluation: evalName?.trim(),
+    body: body?.trim() ?? "",
+  };
+}
+
+export default function CommitMessage({
+  message,
+  className = "",
+  compact = false,
+}: CommitMessageProps) {
+  const parsed = parseCommitMessage(message);
+
+  if (!parsed.isAIGenerated) {
+    return message ? <span className={className}>{message}</span> : null;
+  }
+
+  const metaParts: string[] = [];
+  if (parsed.fromVersion !== undefined) {
+    metaParts.push(`From v${parsed.fromVersion}`);
+  }
+  if (parsed.evaluation) {
+    metaParts.push(`Eval: ${parsed.evaluation}`);
+  }
+
+  return (
+    <div className={`space-y-1 ${className}`}>
+      <div className="flex flex-wrap items-center gap-1.5">
+        <span className="inline-flex items-center px-1.5 py-0.5 rounded-full text-[10px] font-semibold uppercase tracking-wide bg-accent-primary/10 text-accent-primary">
+          AI Generated
+        </span>
+        {metaParts.length > 0 && (
+          <span className="text-xs text-text-secondary">
+            {metaParts.join(" • ")}
+          </span>
+        )}
+      </div>
+      {parsed.body && (
+        <div
+          className={
+            compact
+              ? "text-xs text-text-primary max-h-24 overflow-y-auto pr-1 whitespace-pre-wrap"
+              : "text-xs text-text-primary whitespace-pre-wrap"
+          }
+        >
+          {parsed.body}
+        </div>
+      )}
+    </div>
+  );
+}
diff --git a/app/components/evaluations/DetailedResultsTable.tsx b/app/components/evaluations/DetailedResultsTable.tsx
index 20cebfcc..8d6a9a2c 100644
--- a/app/components/evaluations/DetailedResultsTable.tsx
+++ b/app/components/evaluations/DetailedResultsTable.tsx
@@ -16,6 +16,7 @@ import {
 import { formatScoreValue, getScoreByName } from "@/app/lib/utils";
 import { InfoTooltip } from "@/app/components/ui";
 import { GroupedResultsTable } from "@/app/components/evaluations";
+import { MarkdownContent } from "@/app/components/chat";
 
 interface DetailedResultsTableProps {
   job: EvalJob;
@@ -175,7 +176,10 @@ export default function DetailedResultsTable({
 
                   <td className="px-4 py-3 align-top bg-bg-primary">
                     <div className="text-sm overflow-auto text-text-primary leading-normal max-h-[150px] wrap-break-word">
-                      {answer}
+                      <MarkdownContent
+                        text={answer}
+                        className={"text-sm leading-relaxed"}
+                      />
                     </div>
                   </td>
 
@@ -190,7 +194,7 @@ export default function DetailedResultsTable({
                       >
                         <div className="flex items-center justify-center gap-2">
                           <div
-                            className={`inline-block px-2 py-1 rounded text-xs font-medium border-border ${bg === "transparent" ? "border" : ""}`}
+                            className={`inline-block px-2 py-1 rounded-full text-xs font-medium border-border ${bg === "transparent" ? "border" : ""}`}
                             style={{
                               color,
                               backgroundColor: bg,
diff --git a/app/components/icons/prompt-editor/SpinnerIcon.tsx b/app/components/icons/prompt-editor/SpinnerIcon.tsx
index 31fc607f..87c1112a 100644
--- a/app/components/icons/prompt-editor/SpinnerIcon.tsx
+++ b/app/components/icons/prompt-editor/SpinnerIcon.tsx
@@ -5,25 +5,10 @@ interface IconProps {
 
 export default function SpinnerIcon({ className, style }: IconProps) {
   return (
-    <svg
-      className={`w-3 h-3 animate-spin ${className ?? ""}`}
-      viewBox="0 0 24 24"
-      fill="none"
+    <span
+      aria-hidden
       style={style}
-    >
-      <circle
-        className="opacity-25"
-        cx="12"
-        cy="12"
-        r="10"
-        stroke="currentColor"
-        strokeWidth="4"
-      />
-      <path
-        className="opacity-75"
-        fill="currentColor"
-        d="M4 12a8 8 0 018-8v4a4 4 0 00-4 4H4z"
-      />
-    </svg>
+      className={`inline-block w-3.5 h-3.5 rounded-full animate-spin border-2 border-accent-primary/20 border-t-accent-primary [animation-duration:0.7s] ${className ?? ""}`}
+    />
   );
 }
diff --git a/app/components/index.ts b/app/components/index.ts
index 81cff22f..546e1aab 100644
--- a/app/components/index.ts
+++ b/app/components/index.ts
@@ -4,3 +4,4 @@ export { default as VersionPill } from "./configurations/VersionPill";
 export { default as DatasetListSkeleton } from "./DatasetListSkeleton";
 export { default as RunsListSkeleton } from "./RunsListSkeleton";
 export { default as ResultsTableSkeleton } from "./ResultsTableSkeleton";
+export { default as CommitMessage } from "./CommitMessage";
diff --git a/app/components/prompt-editor/ConfigEditorPane.tsx b/app/components/prompt-editor/ConfigEditorPane.tsx
index 721115b5..52670a82 100644
--- a/app/components/prompt-editor/ConfigEditorPane.tsx
+++ b/app/components/prompt-editor/ConfigEditorPane.tsx
@@ -69,7 +69,6 @@ export default function ConfigEditorPane({
       .catch(() => {});
   }, [apiKey]);
 
-  // Close the save modal when a save just completed successfully.
   useEffect(() => {
     if (wasSavingRef.current && !isSaving && commitMessage === "") {
       setShowSaveModal(false);
diff --git a/app/components/prompt-editor/HistorySidebar.tsx b/app/components/prompt-editor/HistorySidebar.tsx
index 7d37e9d4..09337441 100644
--- a/app/components/prompt-editor/HistorySidebar.tsx
+++ b/app/components/prompt-editor/HistorySidebar.tsx
@@ -1,6 +1,6 @@
 import { Dispatch, SetStateAction, useCallback, useState } from "react";
 import { Button, Loader } from "@/app/components/ui";
-import { VersionPill } from "@/app/components";
+import { CommitMessage, VersionPill } from "@/app/components";
 import { ArrowLeftIcon } from "@/app/components/icons";
 import {
   ConfigPublic,
@@ -53,8 +53,8 @@ function VersionRow({
       </div>
 
       {item.commit_message && (
-        <div className="text-xs mb-1 text-text-primary">
-          {item.commit_message}
+        <div className="mb-2">
+          <CommitMessage message={item.commit_message} compact />
         </div>
       )}
 
@@ -93,7 +93,6 @@ function VersionRow({
   );
 }
 
-// Single-config version history (when a config is loaded in the editor)
 interface SingleConfigHistoryProps {
   configId: string;
   configName: string;
diff --git a/app/lib/types/commit.ts b/app/lib/types/commit.ts
new file mode 100644
index 00000000..b066c5e4
--- /dev/null
+++ b/app/lib/types/commit.ts
@@ -0,0 +1,12 @@
+export interface ParsedCommit {
+  isAIGenerated: boolean;
+  fromVersion?: number;
+  evaluation?: string;
+  body: string;
+}
+
+export interface CommitMessageProps {
+  message: string | null | undefined;
+  className?: string;
+  compact?: boolean;
+}