diff --git a/ui/src/components/AnimatedPaperclipIcon.tsx b/ui/src/components/AnimatedPaperclipIcon.tsx
new file mode 100644
index 00000000000..bb3b624ee6c
--- /dev/null
+++ b/ui/src/components/AnimatedPaperclipIcon.tsx
@@ -0,0 +1,23 @@
+import type { SVGProps } from "react";
+import { cn } from "../lib/utils";
+
+export function AnimatedPaperclipIcon({ className, ...props }: SVGProps<SVGSVGElement>) {
+  return (
+    <svg
+      viewBox="-1 -1 26 26"
+      className={cn("paperclip-thinking-icon", className)}
+      aria-hidden="true"
+      {...props}
+    >
+      <path
+        className="paperclip-thinking-icon-path"
+        d="M16 6 l-8.414 8.586 a2.000 2.000 0 0 0 2.828 2.828 l8.414 -8.586 a4.000 4.000 0 1 0 -5.657 -5.657 l-8.379 8.551 a6.000 6.000 0 1 0 8.485 8.485 l8.379 -8.551"
+        fill="none"
+        stroke="currentColor"
+        strokeWidth="2"
+        strokeLinecap="round"
+        strokeLinejoin="round"
+      />
+    </svg>
+  );
+}
diff --git a/ui/src/components/IssueChatThread.tsx b/ui/src/components/IssueChatThread.tsx
index d0603968f1c..a4b5cf75b22 100644
--- a/ui/src/components/IssueChatThread.tsx
+++ b/ui/src/components/IssueChatThread.tsx
@@ -167,6 +167,7 @@ import { IssueBlockedNotice } from "./IssueBlockedNotice";
 import { IssueAssignedBacklogNotice } from "./IssueAssignedBacklogNotice";
 import { IssueRecoveryActionCard, type RecoveryResolveOutcome } from "./IssueRecoveryActionCard";
 import { SourceTrustBadge } from "./SourceTrustBadge";
+import { AnimatedPaperclipIcon } from "./AnimatedPaperclipIcon";
 
 interface IssueChatMessageContext {
   feedbackDataSharingPreference: FeedbackDataSharingPreference;
@@ -893,10 +894,10 @@ function IssueChatChainOfThought({
         onClick={() => hasContent && setExpanded((v) => !v)}
       >
         <span className="inline-flex items-center gap-2 text-sm font-medium text-foreground/80">
-          {agentIcon ? (
+          {isActive ? (
+            <AnimatedPaperclipIcon className="h-4 w-4 shrink-0 text-muted-foreground" />
+          ) : agentIcon ? (
             <AgentIcon icon={agentIcon} className="h-4 w-4 shrink-0" />
-          ) : isActive ? (
-            <Loader2 className="h-4 w-4 shrink-0 animate-spin text-muted-foreground" />
           ) : (
             <span className="flex h-4 w-4 shrink-0 items-center justify-center">
               <span className="h-1.5 w-1.5 rounded-full bg-emerald-500/70" />
@@ -1021,7 +1022,7 @@ function IssueChatRollingToolPart({ toolParts }: { toolParts: ToolCallMessagePar
     <div className="flex gap-2 px-1">
       <div className="flex flex-col items-center pt-0.5">
         {isRunning ? (
-          <Loader2 className="h-3.5 w-3.5 shrink-0 animate-spin text-muted-foreground/50" />
+          <AnimatedPaperclipIcon className="h-3.5 w-3.5 shrink-0 text-muted-foreground/50" />
         ) : (
           <ToolIcon className="h-3.5 w-3.5 shrink-0 text-muted-foreground/50" />
         )}
@@ -1792,7 +1793,7 @@ function IssueChatAssistantMessage({
               ) : null}
               {isRunning ? (
                 <span className="inline-flex items-center gap-1 rounded-full border border-cyan-400/40 bg-cyan-500/10 px-2 py-0.5 text-[10px] font-medium uppercase tracking-[0.14em] text-cyan-700 dark:text-cyan-200">
-                  <Loader2 className="h-3 w-3 animate-spin" />
+                  <AnimatedPaperclipIcon className="h-3 w-3" />
                   Running
                 </span>
               ) : null}
@@ -1810,11 +1811,7 @@ function IssueChatAssistantMessage({
                 {message.content.length === 0 && waitingText ? (
                   <div className="flex items-center gap-2.5 rounded-lg px-1 py-2">
                     <span className="inline-flex items-center gap-2 text-sm font-medium text-foreground/80">
-                      {agentIcon ? (
-                        <AgentIcon icon={agentIcon} className="h-4 w-4 shrink-0" />
-                      ) : (
-                        <Loader2 className="h-4 w-4 shrink-0 animate-spin text-muted-foreground" />
-                      )}
+                      <AnimatedPaperclipIcon className="h-4 w-4 shrink-0 text-muted-foreground" />
                       <span className="shimmer-text">{waitingText}</span>
                     </span>
                   </div>
diff --git a/ui/src/components/IssueChatThreadClassic.tsx b/ui/src/components/IssueChatThreadClassic.tsx
index 1763bef99c2..22f61e3d41b 100644
--- a/ui/src/components/IssueChatThreadClassic.tsx
+++ b/ui/src/components/IssueChatThreadClassic.tsx
@@ -154,6 +154,7 @@ import { IssueBlockedNotice } from "./IssueBlockedNotice";
 import { IssueAssignedBacklogNotice } from "./IssueAssignedBacklogNotice";
 import { IssueRecoveryActionCard, type RecoveryResolveOutcome } from "./IssueRecoveryActionCard";
 import { SourceTrustBadge } from "./SourceTrustBadge";
+import { AnimatedPaperclipIcon } from "./AnimatedPaperclipIcon";
 
 interface IssueChatMessageContext {
   feedbackDataSharingPreference: FeedbackDataSharingPreference;
@@ -918,10 +919,10 @@ function IssueChatChainOfThought({
         onClick={() => hasContent && setExpanded((v) => !v)}
       >
         <span className="inline-flex items-center gap-2 text-sm font-medium text-foreground/80">
-          {agentIcon ? (
+          {isActive ? (
+            <AnimatedPaperclipIcon className="h-4 w-4 shrink-0 text-muted-foreground" />
+          ) : agentIcon ? (
             <AgentIcon icon={agentIcon} className="h-4 w-4 shrink-0" />
-          ) : isActive ? (
-            <Loader2 className="h-4 w-4 shrink-0 animate-spin text-muted-foreground" />
           ) : (
             <span className="flex h-4 w-4 shrink-0 items-center justify-center">
               <span className="h-1.5 w-1.5 rounded-full bg-emerald-500/70" />
@@ -1046,7 +1047,7 @@ function IssueChatRollingToolPart({ toolParts }: { toolParts: ToolCallMessagePar
     <div className="flex gap-2 px-1">
       <div className="flex flex-col items-center pt-0.5">
         {isRunning ? (
-          <Loader2 className="h-3.5 w-3.5 shrink-0 animate-spin text-muted-foreground/50" />
+          <AnimatedPaperclipIcon className="h-3.5 w-3.5 shrink-0 text-muted-foreground/50" />
         ) : (
           <ToolIcon className="h-3.5 w-3.5 shrink-0 text-muted-foreground/50" />
         )}
@@ -1642,7 +1643,7 @@ function IssueChatAssistantMessage({
               ) : null}
               {isRunning ? (
                 <span className="inline-flex items-center gap-1 rounded-full border border-cyan-400/40 bg-cyan-500/10 px-2 py-0.5 text-[10px] font-medium uppercase tracking-[0.14em] text-cyan-700 dark:text-cyan-200">
-                  <Loader2 className="h-3 w-3 animate-spin" />
+                  <AnimatedPaperclipIcon className="h-3 w-3" />
                   Running
                 </span>
               ) : null}
@@ -1660,11 +1661,7 @@ function IssueChatAssistantMessage({
                 {message.content.length === 0 && waitingText ? (
                   <div className="flex items-center gap-2.5 rounded-lg px-1 py-2">
                     <span className="inline-flex items-center gap-2 text-sm font-medium text-foreground/80">
-                      {agentIcon ? (
-                        <AgentIcon icon={agentIcon} className="h-4 w-4 shrink-0" />
-                      ) : (
-                        <Loader2 className="h-4 w-4 shrink-0 animate-spin text-muted-foreground" />
-                      )}
+                      <AnimatedPaperclipIcon className="h-4 w-4 shrink-0 text-muted-foreground" />
                       <span className="shimmer-text">{waitingText}</span>
                     </span>
                   </div>
diff --git a/ui/src/components/transcript/RunTranscriptView.tsx b/ui/src/components/transcript/RunTranscriptView.tsx
index a9130f8cde8..7754a9cd60e 100644
--- a/ui/src/components/transcript/RunTranscriptView.tsx
+++ b/ui/src/components/transcript/RunTranscriptView.tsx
@@ -12,6 +12,7 @@ import {
   User,
   Wrench,
 } from "lucide-react";
+import { AnimatedPaperclipIcon } from "../AnimatedPaperclipIcon";
 
 export type TranscriptMode = "nice" | "raw";
 export type TranscriptDensity = "comfortable" | "compact";
@@ -742,7 +743,7 @@ function TranscriptToolCard({
         ) : block.status === "completed" ? (
           <Check className={iconClass} />
         ) : (
-          <Wrench className={iconClass} />
+          <AnimatedPaperclipIcon className={iconClass} />
         )}
         <div className="min-w-0 flex-1">
           <div className="flex flex-wrap items-center gap-x-2 gap-y-1">
@@ -855,10 +856,13 @@ function TranscriptCommandGroup({
                 isRunning
                   ? "border-cyan-500/25 bg-cyan-500/[0.08] text-cyan-600 dark:text-cyan-300"
                   : "border-border/70 bg-background text-foreground/55",
-                isRunning && "animate-pulse",
               )}
             >
-              <TerminalSquare className="h-3.5 w-3.5" />
+              {isRunning ? (
+                <AnimatedPaperclipIcon className="h-3.5 w-3.5" />
+              ) : (
+                <TerminalSquare className="h-3.5 w-3.5" />
+              )}
             </span>
           ))}
         </div>
@@ -980,10 +984,13 @@ function TranscriptToolGroup({
                     : isItemError
                       ? "border-red-500/25 bg-red-500/[0.08] text-red-600 dark:text-red-300"
                       : "border-border/70 bg-background text-foreground/55",
-                  isItemRunning && "animate-pulse",
                 )}
               >
-                <Wrench className="h-3.5 w-3.5" />
+                {isItemRunning ? (
+                  <AnimatedPaperclipIcon className="h-3.5 w-3.5" />
+                ) : (
+                  <Wrench className="h-3.5 w-3.5" />
+                )}
               </span>
             );
           })}
@@ -1020,7 +1027,11 @@ function TranscriptToolGroup({
                       ? "border-cyan-500/25 bg-cyan-500/[0.08] text-cyan-600 dark:text-cyan-300"
                       : "border-border/70 bg-background text-foreground/55",
                 )}>
-                  <Wrench className="h-3 w-3" />
+                  {item.status === "running" ? (
+                    <AnimatedPaperclipIcon className="h-3 w-3" />
+                  ) : (
+                    <Wrench className="h-3 w-3" />
+                  )}
                 </span>
                 <span className={cn("text-[10px] font-semibold uppercase tracking-[0.14em] text-muted-foreground")}>
                   {humanizeLabel(item.name)}
diff --git a/ui/src/index.css b/ui/src/index.css
index 6c5e2b7c581..5d7ab145057 100644
--- a/ui/src/index.css
+++ b/ui/src/index.css
@@ -464,12 +464,55 @@
   animation: shimmer-text-slide 2.5s linear infinite;
 }
 
+.paperclip-thinking-icon {
+  transform-origin: 50% 50%;
+}
+
+@keyframes paperclip-thinking-draw {
+  0% {
+    stroke-dasharray: 0 85.717;
+    stroke-dashoffset: -85.717;
+    opacity: 1;
+    animation-timing-function: cubic-bezier(0.455, 0.03, 0.515, 0.955);
+  }
+  39.0625% {
+    stroke-dasharray: 85.717 85.717;
+    stroke-dashoffset: 0;
+    opacity: 1;
+    animation-timing-function: cubic-bezier(0.55, 0.055, 0.675, 0.19);
+  }
+  78.125% {
+    stroke-dasharray: 0 85.717;
+    stroke-dashoffset: 0;
+    opacity: 1;
+  }
+  78.225% {
+    opacity: 0;
+  }
+  100% {
+    stroke-dasharray: 0 85.717;
+    stroke-dashoffset: 0;
+    opacity: 0;
+  }
+}
+
+.paperclip-thinking-icon-path {
+  animation: paperclip-thinking-draw 1s linear infinite;
+}
+
 @media (prefers-reduced-motion: reduce) {
   .shimmer-text {
     animation: none;
     -webkit-text-fill-color: unset;
     background: none;
   }
+
+  .paperclip-thinking-icon-path {
+    animation: none;
+    opacity: 1;
+    stroke-dasharray: 85.717 85.717;
+    stroke-dashoffset: 0;
+  }
 }
 
 /* Agent heartbeat capsule motion (PAP-75).