diff --git a/package-lock.json b/package-lock.json
index f62ba518..878a4f5b 100644
--- a/package-lock.json
+++ b/package-lock.json
@@ -10403,6 +10403,7 @@
         "diff": "^7.0.0",
         "dotenv": "^16.4.7",
         "fast-glob": "^3.3.3",
+        "shell-quote": "^1.8.2",
         "sqlite3": "^5.1.7"
       },
       "devDependencies": {
diff --git a/package.json b/package.json
index a0b07634..c60f07d0 100644
--- a/package.json
+++ b/package.json
@@ -27,9 +27,9 @@
     "bundle": "esbuild packages/cli/index.ts --bundle --outfile=bundle/gemini.js --platform=node --format=esm --banner:js=\"import { createRequire } from 'module'; const require = createRequire(import.meta.url); globalThis.__filename = require('url').fileURLToPath(import.meta.url); globalThis.__dirname = require('path').dirname(globalThis.__filename);\" && bash scripts/copy_bundle_assets.sh"
   },
   "devDependencies": {
+    "@types/mime-types": "^2.1.4",
     "@vitest/coverage-v8": "^3.1.1",
     "esbuild": "^0.25.4",
-    "@types/mime-types": "^2.1.4",
     "eslint": "^9.24.0",
     "eslint-config-prettier": "^10.1.2",
     "eslint-plugin-import": "^2.31.0",
diff --git a/packages/cli/src/ui/components/messages/ToolGroupMessage.tsx b/packages/cli/src/ui/components/messages/ToolGroupMessage.tsx
index 4b2c7dfe..8bcde3bb 100644
--- a/packages/cli/src/ui/components/messages/ToolGroupMessage.tsx
+++ b/packages/cli/src/ui/components/messages/ToolGroupMessage.tsx
@@ -29,6 +29,8 @@ export const ToolGroupMessage: React.FC<ToolGroupMessageProps> = ({
 
   const staticHeight = /* border */ 2 + /* marginBottom */ 1;
 
+  // only prompt for tool approval on the first 'confirming' tool in the list
+  // note, after the CTA, this automatically moves over to the next 'confirming' tool
   const toolAwaitingApproval = useMemo(
     () => toolCalls.find((tc) => tc.status === ToolCallStatus.Confirming),
     [toolCalls],
@@ -50,27 +52,38 @@ export const ToolGroupMessage: React.FC<ToolGroupMessageProps> = ({
       borderColor={borderColor}
       marginBottom={1}
     >
-      {toolCalls.map((tool) => (
-        <Box key={tool.callId} flexDirection="column">
-          <ToolMessage
-            key={tool.callId}
-            callId={tool.callId}
-            name={tool.name}
-            description={tool.description}
-            resultDisplay={tool.resultDisplay}
-            status={tool.status}
-            confirmationDetails={tool.confirmationDetails}
-            availableTerminalHeight={availableTerminalHeight - staticHeight}
-          />
-          {tool.status === ToolCallStatus.Confirming &&
-            tool.callId === toolAwaitingApproval?.callId &&
-            tool.confirmationDetails && (
-              <ToolConfirmationMessage
+      {toolCalls.map((tool) => {
+        const isConfirming = toolAwaitingApproval?.callId === tool.callId;
+        return (
+          <Box key={tool.callId} flexDirection="column">
+            <Box flexDirection="row" alignItems="center">
+              <ToolMessage
+                callId={tool.callId}
+                name={tool.name}
+                description={tool.description}
+                resultDisplay={tool.resultDisplay}
+                status={tool.status}
                 confirmationDetails={tool.confirmationDetails}
-              ></ToolConfirmationMessage>
-            )}
-        </Box>
-      ))}
+                availableTerminalHeight={availableTerminalHeight - staticHeight}
+                emphasis={
+                  isConfirming
+                    ? 'high'
+                    : toolAwaitingApproval
+                      ? 'low'
+                      : 'medium'
+                }
+              />
+            </Box>
+            {tool.status === ToolCallStatus.Confirming &&
+              isConfirming &&
+              tool.confirmationDetails && (
+                <ToolConfirmationMessage
+                  confirmationDetails={tool.confirmationDetails}
+                />
+              )}
+          </Box>
+        );
+      })}
     </Box>
   );
 };
diff --git a/packages/cli/src/ui/components/messages/ToolMessage.tsx b/packages/cli/src/ui/components/messages/ToolMessage.tsx
index 32b23b9e..32b3b7e8 100644
--- a/packages/cli/src/ui/components/messages/ToolMessage.tsx
+++ b/packages/cli/src/ui/components/messages/ToolMessage.tsx
@@ -12,8 +12,15 @@ import { DiffRenderer } from './DiffRenderer.js';
 import { Colors } from '../../colors.js';
 import { MarkdownDisplay } from '../../utils/MarkdownDisplay.js';
 
+const STATIC_HEIGHT = 1;
+const RESERVED_LINE_COUNT = 5; // for tool name, status, padding etc.
+const STATUS_INDICATOR_WIDTH = 3;
+
+export type TextEmphasis = 'high' | 'medium' | 'low';
+
 export interface ToolMessageProps extends IndividualToolCallDisplay {
   availableTerminalHeight: number;
+  emphasis?: TextEmphasis;
 }
 
 export const ToolMessage: React.FC<ToolMessageProps> = ({
@@ -22,63 +29,45 @@ export const ToolMessage: React.FC<ToolMessageProps> = ({
   resultDisplay,
   status,
   availableTerminalHeight,
+  emphasis = 'medium',
 }) => {
-  const statusIndicatorWidth = 3;
-  const hasResult = resultDisplay && resultDisplay.toString().trim().length > 0;
-  const staticHeight = /* Header */ 1;
-
-  let displayableResult = resultDisplay;
-  let hiddenLines = 0;
+  const contentHeightEstimate =
+    availableTerminalHeight - STATIC_HEIGHT - RESERVED_LINE_COUNT;
+  const resultIsString =
+    typeof resultDisplay === 'string' && resultDisplay.trim().length > 0;
+  const lines = React.useMemo(
+    () => (resultIsString ? resultDisplay.split('\n') : []),
+    [resultIsString, resultDisplay],
+  );
 
   // Truncate the overall string content if it's too long.
   // MarkdownRenderer will handle specific truncation for code blocks within this content.
-  if (typeof resultDisplay === 'string' && resultDisplay.length > 0) {
-    const lines = resultDisplay.split('\n');
-    // Estimate available height for this specific tool message content area
-    // This is a rough estimate; ideally, we'd have a more precise measurement.
-    const contentHeightEstimate = availableTerminalHeight - staticHeight - 5; // Subtracting lines for tool name, status, padding etc.
-    if (lines.length > contentHeightEstimate && contentHeightEstimate > 0) {
-      displayableResult = lines.slice(0, contentHeightEstimate).join('\n');
-      hiddenLines = lines.length - contentHeightEstimate;
-    }
-  }
+  // Estimate available height for this specific tool message content area
+  // This is a rough estimate; ideally, we'd have a more precise measurement.
+  const displayableResult = React.useMemo(
+    () =>
+      resultIsString
+        ? lines.slice(0, contentHeightEstimate).join('\n')
+        : resultDisplay,
+    [lines, resultIsString, contentHeightEstimate, resultDisplay],
+  );
+  const hiddenLines = lines.length - contentHeightEstimate;
 
   return (
     <Box paddingX={1} paddingY={0} flexDirection="column">
       <Box minHeight={1}>
         {/* Status Indicator */}
-        <Box minWidth={statusIndicatorWidth}>
-          {(status === ToolCallStatus.Pending ||
-            status === ToolCallStatus.Executing) && <Spinner type="dots" />}
-          {status === ToolCallStatus.Success && (
-            <Text color={Colors.AccentGreen}>✔</Text>
-          )}
-          {status === ToolCallStatus.Confirming && (
-            <Text color={Colors.AccentYellow}>?</Text>
-          )}
-          {status === ToolCallStatus.Canceled && (
-            <Text color={Colors.AccentYellow} bold>
-              -
-            </Text>
-          )}
-          {status === ToolCallStatus.Error && (
-            <Text color={Colors.AccentRed} bold>
-              x
-            </Text>
-          )}
-        </Box>
-        <Box>
-          <Text
-            wrap="truncate-end"
-            strikethrough={status === ToolCallStatus.Canceled}
-          >
-            <Text bold>{name}</Text>{' '}
-            <Text color={Colors.SubtleComment}>{description}</Text>
-          </Text>
-        </Box>
+        <ToolStatusIndicator status={status} />
+        <ToolInfo
+          name={name}
+          status={status}
+          description={description}
+          emphasis={emphasis}
+        />
+        {emphasis === 'high' && <TrailingIndicator />}
       </Box>
-      {hasResult && (
-        <Box paddingLeft={statusIndicatorWidth} width="100%">
+      {displayableResult && (
+        <Box paddingLeft={STATUS_INDICATOR_WIDTH} width="100%">
           <Box flexDirection="column">
             {typeof displayableResult === 'string' && (
               <Box flexDirection="column">
@@ -89,7 +78,7 @@ export const ToolMessage: React.FC<ToolMessageProps> = ({
                 />
               </Box>
             )}
-            {typeof displayableResult === 'object' && (
+            {typeof displayableResult !== 'string' && (
               <DiffRenderer
                 diffContent={displayableResult.fileDiff}
                 filename={displayableResult.fileName}
@@ -109,3 +98,76 @@ export const ToolMessage: React.FC<ToolMessageProps> = ({
     </Box>
   );
 };
+
+type ToolStatusIndicator = {
+  status: ToolCallStatus;
+};
+const ToolStatusIndicator: React.FC<ToolStatusIndicator> = ({ status }) => (
+  <Box minWidth={STATUS_INDICATOR_WIDTH}>
+    {status === ToolCallStatus.Pending && (
+      <Text color={Colors.AccentGreen}>o</Text>
+    )}
+    {status === ToolCallStatus.Executing && <Spinner type="dots" />}
+    {status === ToolCallStatus.Success && (
+      <Text color={Colors.AccentGreen}>✔</Text>
+    )}
+    {status === ToolCallStatus.Confirming && (
+      <Text color={Colors.AccentYellow}>?</Text>
+    )}
+    {status === ToolCallStatus.Canceled && (
+      <Text color={Colors.AccentYellow} bold>
+        -
+      </Text>
+    )}
+    {status === ToolCallStatus.Error && (
+      <Text color={Colors.AccentRed} bold>
+        x
+      </Text>
+    )}
+  </Box>
+);
+
+type ToolInfo = {
+  name: string;
+  description: string;
+  status: ToolCallStatus;
+  emphasis: TextEmphasis;
+};
+const ToolInfo: React.FC<ToolInfo> = ({
+  name,
+  description,
+  status,
+  emphasis,
+}) => {
+  const nameColor = React.useMemo<string>(() => {
+    switch (emphasis) {
+      case 'high':
+        return Colors.Foreground;
+      case 'medium':
+        return Colors.Foreground;
+      case 'low':
+        return Colors.SubtleComment;
+      default: {
+        const exhaustiveCheck: never = emphasis;
+        return exhaustiveCheck;
+      }
+    }
+  }, [emphasis]);
+  return (
+    <Box>
+      <Text
+        wrap="truncate-end"
+        strikethrough={status === ToolCallStatus.Canceled}
+      >
+        <Text color={nameColor} bold>
+          {name}
+        </Text>{' '}
+        <Text color={Colors.SubtleComment}>{description}</Text>
+      </Text>
+    </Box>
+  );
+};
+
+const TrailingIndicator: React.FC = () => (
+  <Text color={Colors.Foreground}> ←</Text>
+);
diff --git a/packages/cli/src/ui/hooks/useToolScheduler.ts b/packages/cli/src/ui/hooks/useToolScheduler.ts
index 8bcc0ae9..a5770d36 100644
--- a/packages/cli/src/ui/hooks/useToolScheduler.ts
+++ b/packages/cli/src/ui/hooks/useToolScheduler.ts
@@ -184,48 +184,53 @@ export function useToolScheduler(
 
   useEffect(() => {
     // effect for executing scheduled tool calls
-    if (toolCalls.every((t) => t.status === 'scheduled')) {
+    const allToolsConfirmed = toolCalls.every(
+      (t) => t.status === 'scheduled' || t.status === 'cancelled',
+    );
+    if (allToolsConfirmed) {
       const signal = abortController.signal;
-      toolCalls.forEach((c) => {
-        const callId = c.request.callId;
-        setToolCalls(setStatus(c.request.callId, 'executing'));
-        c.tool
-          .execute(c.request.args, signal)
-          .then((result) => {
-            if (signal.aborted) {
-              setToolCalls(
-                setStatus(callId, 'cancelled', 'Cancelled during execution'),
-              );
-              return;
-            }
-            const functionResponse: Part = {
-              functionResponse: {
-                name: c.request.name,
-                id: callId,
-                response: { output: result.llmContent },
-              },
-            };
-            const response: ToolCallResponseInfo = {
-              callId,
-              responsePart: functionResponse,
-              resultDisplay: result.returnDisplay,
-              error: undefined,
-            };
-            setToolCalls(setStatus(callId, 'success', response));
-          })
-          .catch((e) =>
-            setToolCalls(
-              setStatus(
+      toolCalls
+        .filter((t) => t.status === 'scheduled')
+        .forEach((t) => {
+          const callId = t.request.callId;
+          setToolCalls(setStatus(t.request.callId, 'executing'));
+          t.tool
+            .execute(t.request.args, signal)
+            .then((result) => {
+              if (signal.aborted) {
+                setToolCalls(
+                  setStatus(callId, 'cancelled', 'Cancelled during execution'),
+                );
+                return;
+              }
+              const functionResponse: Part = {
+                functionResponse: {
+                  name: t.request.name,
+                  id: callId,
+                  response: { output: result.llmContent },
+                },
+              };
+              const response: ToolCallResponseInfo = {
                 callId,
-                'error',
-                toolErrorResponse(
-                  c.request,
-                  e instanceof Error ? e : new Error(String(e)),
+                responsePart: functionResponse,
+                resultDisplay: result.returnDisplay,
+                error: undefined,
+              };
+              setToolCalls(setStatus(callId, 'success', response));
+            })
+            .catch((e) =>
+              setToolCalls(
+                setStatus(
+                  callId,
+                  'error',
+                  toolErrorResponse(
+                    t.request,
+                    e instanceof Error ? e : new Error(String(e)),
+                  ),
                 ),
               ),
-            ),
-          );
-      });
+            );
+        });
     }
   }, [toolCalls, toolRegistry, abortController.signal]);