diff --git a/messages/en-US.json b/messages/en-US.json
index 0e9cb5786..9a23043d5 100644
--- a/messages/en-US.json
+++ b/messages/en-US.json
@@ -3062,7 +3062,7 @@
     "streamingDatadogTitle": "Datadog",
     "streamingDatadogDescription": "Forward events directly to your Datadog account.",
     "streamingTypePickerDescription": "Choose a destination type to get started.",
-    "streamingFailedToLoad": "Failed to load destinations",
+    "streamingLastSyncError": "An error occurred on the last sync",
     "streamingUnexpectedError": "An unexpected error occurred.",
     "streamingFailedToUpdate": "Failed to update destination",
     "streamingDeletedSuccess": "Destination deleted successfully",
diff --git a/server/db/pg/schema/privateSchema.ts b/server/db/pg/schema/privateSchema.ts
index 0f1914fad..6137743bf 100644
--- a/server/db/pg/schema/privateSchema.ts
+++ b/server/db/pg/schema/privateSchema.ts
@@ -439,6 +439,8 @@ export const eventStreamingDestinations = pgTable(
         type: varchar("type", { length: 50 }).notNull(), // e.g. "http", "kafka", etc.
         config: text("config").notNull(), // JSON string with the configuration for the destination
         enabled: boolean("enabled").notNull().default(true),
+        lastError: text("lastError"), // last send error message, null if healthy
+        lastErrorAt: bigint("lastErrorAt", { mode: "number" }), // epoch ms of last error, null if healthy
         createdAt: bigint("createdAt", { mode: "number" }).notNull(),
         updatedAt: bigint("updatedAt", { mode: "number" }).notNull()
     }
diff --git a/server/db/sqlite/schema/privateSchema.ts b/server/db/sqlite/schema/privateSchema.ts
index 05c917887..a25183055 100644
--- a/server/db/sqlite/schema/privateSchema.ts
+++ b/server/db/sqlite/schema/privateSchema.ts
@@ -445,6 +445,8 @@ export const eventStreamingDestinations = sqliteTable(
         enabled: integer("enabled", { mode: "boolean" })
             .notNull()
             .default(true),
+        lastError: text("lastError"), // last send error message, null if healthy
+        lastErrorAt: integer("lastErrorAt"), // epoch ms of last error, null if healthy
         createdAt: integer("createdAt").notNull(),
         updatedAt: integer("updatedAt").notNull()
     }
diff --git a/server/private/lib/logStreaming/LogStreamingManager.ts b/server/private/lib/logStreaming/LogStreamingManager.ts
index a9575fec6..03efc2809 100644
--- a/server/private/lib/logStreaming/LogStreamingManager.ts
+++ b/server/private/lib/logStreaming/LogStreamingManager.ts
@@ -313,6 +313,7 @@ export class LogStreamingManager {
         if (enabledTypes.length === 0) return;
 
         let anyFailure = false;
+        let firstError: string | null = null;
 
         for (const logType of enabledTypes) {
             if (!this.isRunning) break;
@@ -320,6 +321,10 @@ export class LogStreamingManager {
                 await this.processLogType(dest, provider, logType);
             } catch (err) {
                 anyFailure = true;
+                if (firstError === null) {
+                    firstError =
+                        err instanceof Error ? err.message : String(err);
+                }
                 logger.error(
                     `LogStreamingManager: failed to process "${logType}" logs ` +
                         `for destination ${dest.destinationId}`,
@@ -330,6 +335,10 @@ export class LogStreamingManager {
 
         if (anyFailure) {
             this.recordFailure(dest.destinationId);
+            await this.setDestinationError(
+                dest.destinationId,
+                firstError ?? "Unknown error"
+            );
         } else {
             // Any success resets the failure/back-off state
             if (this.failures.has(dest.destinationId)) {
@@ -338,6 +347,7 @@ export class LogStreamingManager {
                     `LogStreamingManager: destination ${dest.destinationId} recovered`
                 );
             }
+            await this.clearDestinationError(dest.destinationId);
         }
     }
 
@@ -759,6 +769,45 @@ export class LogStreamingManager {
     // DB helpers
     // -------------------------------------------------------------------------
 
+    private async setDestinationError(
+        destinationId: number,
+        errorMessage: string
+    ): Promise<void> {
+        // Truncate to 1000 chars so it fits comfortably in the text column.
+        const truncated = errorMessage.slice(0, 1000);
+        try {
+            await db
+                .update(eventStreamingDestinations)
+                .set({ lastError: truncated, lastErrorAt: Date.now() })
+                .where(
+                    eq(eventStreamingDestinations.destinationId, destinationId)
+                );
+        } catch (err) {
+            logger.warn(
+                `LogStreamingManager: could not persist error status for destination ${destinationId}`,
+                err
+            );
+        }
+    }
+
+    private async clearDestinationError(destinationId: number): Promise<void> {
+        try {
+            // Only update if there is actually an error stored, to avoid
+            // unnecessary writes on every successful poll cycle.
+            await db
+                .update(eventStreamingDestinations)
+                .set({ lastError: null, lastErrorAt: null })
+                .where(
+                    eq(eventStreamingDestinations.destinationId, destinationId)
+                );
+        } catch (err) {
+            logger.warn(
+                `LogStreamingManager: could not clear error status for destination ${destinationId}`,
+                err
+            );
+        }
+    }
+
     private async loadEnabledDestinations(): Promise<
         EventStreamingDestination[]
     > {
diff --git a/server/private/routers/eventStreamingDestination/listEventStreamingDestinations.ts b/server/private/routers/eventStreamingDestination/listEventStreamingDestinations.ts
index 10a6c3600..27b5d9a5b 100644
--- a/server/private/routers/eventStreamingDestination/listEventStreamingDestinations.ts
+++ b/server/private/routers/eventStreamingDestination/listEventStreamingDestinations.ts
@@ -51,6 +51,8 @@ export type ListEventStreamingDestinationsResponse = {
         type: string;
         config: string;
         enabled: boolean;
+        lastError: string | null;
+        lastErrorAt: number | null;
         createdAt: number;
         updatedAt: number;
         sendConnectionLogs: boolean;
@@ -79,7 +81,8 @@ async function query(orgId: string, limit: number, offset: number) {
 registry.registerPath({
     method: "get",
     path: "/org/{orgId}/event-streaming-destination",
-    description: "List all event streaming destinations for a specific organization.",
+    description:
+        "List all event streaming destinations for a specific organization.",
     tags: [OpenAPITags.Org],
     request: {
         query: querySchema,
diff --git a/src/app/[orgId]/settings/logs/streaming/page.tsx b/src/app/[orgId]/settings/logs/streaming/page.tsx
index 661fbd786..8579527d0 100644
--- a/src/app/[orgId]/settings/logs/streaming/page.tsx
+++ b/src/app/[orgId]/settings/logs/streaming/page.tsx
@@ -22,7 +22,18 @@ import {
 } from "@app/components/Credenza";
 import { Button } from "@app/components/ui/button";
 import { Switch } from "@app/components/ui/switch";
-import { Globe, MoreHorizontal, Plus } from "lucide-react";
+import {
+    Globe,
+    MoreHorizontal,
+    Plus,
+    AlertCircle,
+    ChevronDown
+} from "lucide-react";
+import {
+    Popover,
+    PopoverContent,
+    PopoverTrigger
+} from "@app/components/ui/popover";
 import { AxiosResponse } from "axios";
 import { build } from "@server/build";
 import Image from "next/image";
@@ -153,6 +164,31 @@ function DestinationCard({
                 )}
             </p>
 
+            {/* Error indicator */}
+            {destination.lastError && (
+                <Popover>
+                    <PopoverTrigger asChild>
+                        <button
+                            type="button"
+                            className="flex items-center gap-1.5 text-left cursor-pointer rounded px-0 hover:opacity-75 transition-opacity"
+                        >
+                            <AlertCircle className="h-3.5 w-3.5 text-destructive shrink-0" />
+                            <p className="text-xs text-destructive">
+                                {t("streamingLastSyncError")}
+                            </p>
+                            <ChevronDown className="h-3 w-3 text-destructive shrink-0 ml-auto" />
+                        </button>
+                    </PopoverTrigger>
+                    <PopoverContent
+                        side="bottom"
+                        align="end"
+                        className="w-80 text-xs break-words"
+                    >
+                        {destination.lastError}
+                    </PopoverContent>
+                </Popover>
+            )}
+
             {/* Footer: edit button + three-dots menu */}
             <div className="mt-auto pt-5 flex gap-2">
                 <Button
diff --git a/src/components/HttpDestinationCredenza.tsx b/src/components/HttpDestinationCredenza.tsx
index e39567332..85d32fd5c 100644
--- a/src/components/HttpDestinationCredenza.tsx
+++ b/src/components/HttpDestinationCredenza.tsx
@@ -19,7 +19,8 @@ import { HorizontalTabs } from "@app/components/HorizontalTabs";
 import { RadioGroup, RadioGroupItem } from "@app/components/ui/radio-group";
 import { Textarea } from "@app/components/ui/textarea";
 import { Checkbox } from "@app/components/ui/checkbox";
-import { Plus, X } from "lucide-react";
+import { Plus, X, AlertCircle } from "lucide-react";
+import { Alert, AlertDescription } from "@app/components/ui/alert";
 import { createApiClient, formatAxiosError } from "@app/lib/api";
 import { useEnvContext } from "@app/hooks/useEnvContext";
 import { toast } from "@app/hooks/useToast";
@@ -56,6 +57,8 @@ export interface Destination {
     sendActionLogs: boolean;
     sendConnectionLogs: boolean;
     sendRequestLogs: boolean;
+    lastError: string | null;
+    lastErrorAt: number | null;
     createdAt: number;
     updatedAt: number;
 }
@@ -122,9 +125,7 @@ function HeadersEditor({ headers, onChange }: HeadersEditorProps) {
                     />
                     <Input
                         value={h.value}
-                        onChange={(e) =>
-                            updateRow(i, "value", e.target.value)
-                        }
+                        onChange={(e) => updateRow(i, "value", e.target.value)}
                         placeholder={t("httpDestHeaderValuePlaceholder")}
                         className="flex-1"
                     />
@@ -200,10 +201,7 @@ export function HttpDestinationCredenza({
         if (!raw) return null;
         try {
             const parsed = new URL(raw);
-            if (
-                parsed.protocol !== "http:" &&
-                parsed.protocol !== "https:"
-            ) {
+            if (parsed.protocol !== "http:" && parsed.protocol !== "https:") {
                 return t("httpDestUrlErrorHttpRequired");
             }
             if (build === "saas" && parsed.protocol !== "https:") {
@@ -216,9 +214,7 @@ export function HttpDestinationCredenza({
     })();
 
     const isValid =
-        cfg.name.trim() !== "" &&
-        cfg.url.trim() !== "" &&
-        urlError === null;
+        cfg.name.trim() !== "" && cfg.url.trim() !== "" && urlError === null;
 
     async function handleSave() {
         if (!isValid) return;
@@ -253,10 +249,7 @@ export function HttpDestinationCredenza({
                 title: editing
                     ? t("httpDestUpdateFailed")
                     : t("httpDestCreateFailed"),
-                description: formatAxiosError(
-                    e,
-                    t("streamingUnexpectedError")
-                )
+                description: formatAxiosError(e, t("streamingUnexpectedError"))
             });
         } finally {
             setSaving(false);
@@ -280,6 +273,14 @@ export function HttpDestinationCredenza({
                 </CredenzaHeader>
 
                 <CredenzaBody>
+                    {editing?.lastError && (
+                        <Alert variant="destructive" className="mb-4">
+                            <AlertCircle className="h-4 w-4" />
+                            <AlertDescription className="break-words">
+                                {editing.lastError}
+                            </AlertDescription>
+                        </Alert>
+                    )}
                     <HorizontalTabs
                         clientSide
                         items={[
@@ -357,7 +358,9 @@ export function HttpDestinationCredenza({
                                                 {t("httpDestAuthNoneTitle")}
                                             </Label>
                                             <p className="text-xs text-muted-foreground mt-0.5">
-                                                {t("httpDestAuthNoneDescription")}
+                                                {t(
+                                                    "httpDestAuthNoneDescription"
+                                                )}
                                             </p>
                                         </div>
                                     </div>
@@ -375,15 +378,21 @@ export function HttpDestinationCredenza({
                                                     htmlFor="auth-bearer"
                                                     className="cursor-pointer font-medium"
                                                 >
-                                                    {t("httpDestAuthBearerTitle")}
+                                                    {t(
+                                                        "httpDestAuthBearerTitle"
+                                                    )}
                                                 </Label>
                                                 <p className="text-xs text-muted-foreground mt-0.5">
-                                                    {t("httpDestAuthBearerDescription")}
+                                                    {t(
+                                                        "httpDestAuthBearerDescription"
+                                                    )}
                                                 </p>
                                             </div>
                                             {cfg.authType === "bearer" && (
                                                 <Input
-                                                    placeholder={t("httpDestAuthBearerPlaceholder")}
+                                                    placeholder={t(
+                                                        "httpDestAuthBearerPlaceholder"
+                                                    )}
                                                     value={
                                                         cfg.bearerToken ?? ""
                                                     }
@@ -411,15 +420,21 @@ export function HttpDestinationCredenza({
                                                     htmlFor="auth-basic"
                                                     className="cursor-pointer font-medium"
                                                 >
-                                                    {t("httpDestAuthBasicTitle")}
+                                                    {t(
+                                                        "httpDestAuthBasicTitle"
+                                                    )}
                                                 </Label>
                                                 <p className="text-xs text-muted-foreground mt-0.5">
-                                                    {t("httpDestAuthBasicDescription")}
+                                                    {t(
+                                                        "httpDestAuthBasicDescription"
+                                                    )}
                                                 </p>
                                             </div>
                                             {cfg.authType === "basic" && (
                                                 <Input
-                                                    placeholder={t("httpDestAuthBasicPlaceholder")}
+                                                    placeholder={t(
+                                                        "httpDestAuthBasicPlaceholder"
+                                                    )}
                                                     value={
                                                         cfg.basicCredentials ??
                                                         ""
@@ -448,16 +463,22 @@ export function HttpDestinationCredenza({
                                                     htmlFor="auth-custom"
                                                     className="cursor-pointer font-medium"
                                                 >
-                                                    {t("httpDestAuthCustomTitle")}
+                                                    {t(
+                                                        "httpDestAuthCustomTitle"
+                                                    )}
                                                 </Label>
                                                 <p className="text-xs text-muted-foreground mt-0.5">
-                                                    {t("httpDestAuthCustomDescription")}
+                                                    {t(
+                                                        "httpDestAuthCustomDescription"
+                                                    )}
                                                 </p>
                                             </div>
                                             {cfg.authType === "custom" && (
                                                 <div className="flex gap-2">
                                                     <Input
-                                                        placeholder={t("httpDestAuthCustomHeaderNamePlaceholder")}
+                                                        placeholder={t(
+                                                            "httpDestAuthCustomHeaderNamePlaceholder"
+                                                        )}
                                                         value={
                                                             cfg.customHeaderName ??
                                                             ""
@@ -472,7 +493,9 @@ export function HttpDestinationCredenza({
                                                         className="flex-1"
                                                     />
                                                     <Input
-                                                        placeholder={t("httpDestAuthCustomHeaderValuePlaceholder")}
+                                                        placeholder={t(
+                                                            "httpDestAuthCustomHeaderValuePlaceholder"
+                                                        )}
                                                         value={
                                                             cfg.customHeaderValue ??
                                                             ""
@@ -593,10 +616,14 @@ export function HttpDestinationCredenza({
                                                 htmlFor="fmt-json-array"
                                                 className="cursor-pointer font-medium"
                                             >
-                                                {t("httpDestFormatJsonArrayTitle")}
+                                                {t(
+                                                    "httpDestFormatJsonArrayTitle"
+                                                )}
                                             </Label>
                                             <p className="text-xs text-muted-foreground mt-0.5">
-                                                {t("httpDestFormatJsonArrayDescription")}
+                                                {t(
+                                                    "httpDestFormatJsonArrayDescription"
+                                                )}
                                             </p>
                                         </div>
                                     </div>
@@ -616,7 +643,9 @@ export function HttpDestinationCredenza({
                                                 {t("httpDestFormatNdjsonTitle")}
                                             </Label>
                                             <p className="text-xs text-muted-foreground mt-0.5">
-                                                {t("httpDestFormatNdjsonDescription")}
+                                                {t(
+                                                    "httpDestFormatNdjsonDescription"
+                                                )}
                                             </p>
                                         </div>
                                     </div>
@@ -636,7 +665,9 @@ export function HttpDestinationCredenza({
                                                 {t("httpDestFormatSingleTitle")}
                                             </Label>
                                             <p className="text-xs text-muted-foreground mt-0.5">
-                                                {t("httpDestFormatSingleDescription")}
+                                                {t(
+                                                    "httpDestFormatSingleDescription"
+                                                )}
                                             </p>
                                         </div>
                                     </div>
@@ -717,7 +748,9 @@ export function HttpDestinationCredenza({
                                             {t("httpDestConnectionLogsTitle")}
                                         </label>
                                         <p className="text-xs text-muted-foreground mt-0.5">
-                                            {t("httpDestConnectionLogsDescription")}
+                                            {t(
+                                                "httpDestConnectionLogsDescription"
+                                            )}
                                         </p>
                                     </div>
                                 </div>
@@ -739,7 +772,9 @@ export function HttpDestinationCredenza({
                                             {t("httpDestRequestLogsTitle")}
                                         </label>
                                         <p className="text-xs text-muted-foreground mt-0.5">
-                                            {t("httpDestRequestLogsDescription")}
+                                            {t(
+                                                "httpDestRequestLogsDescription"
+                                            )}
                                         </p>
                                     </div>
                                 </div>
@@ -764,10 +799,12 @@ export function HttpDestinationCredenza({
                         loading={saving}
                         disabled={!isValid || saving}
                     >
-                        {editing ? t("httpDestSaveChanges") : t("httpDestCreateDestination")}
+                        {editing
+                            ? t("httpDestSaveChanges")
+                            : t("httpDestCreateDestination")}
                     </Button>
                 </CredenzaFooter>
             </CredenzaContent>
         </Credenza>
     );
-}
\ No newline at end of file
+}
diff --git a/src/components/S3DestinationCredenza.tsx b/src/components/S3DestinationCredenza.tsx
index 03b055f58..e6c128805 100644
--- a/src/components/S3DestinationCredenza.tsx
+++ b/src/components/S3DestinationCredenza.tsx
@@ -18,6 +18,8 @@ import { Switch } from "@app/components/ui/switch";
 import { HorizontalTabs } from "@app/components/HorizontalTabs";
 import { RadioGroup, RadioGroupItem } from "@app/components/ui/radio-group";
 import { Checkbox } from "@app/components/ui/checkbox";
+import { AlertCircle } from "lucide-react";
+import { Alert, AlertDescription } from "@app/components/ui/alert";
 import { createApiClient, formatAxiosError } from "@app/lib/api";
 import { useEnvContext } from "@app/hooks/useEnvContext";
 import { toast } from "@app/hooks/useToast";
@@ -164,6 +166,14 @@ export function S3DestinationCredenza({
                 </CredenzaHeader>
 
                 <CredenzaBody>
+                    {editing?.lastError && (
+                        <Alert variant="destructive" className="mb-4">
+                            <AlertCircle className="h-4 w-4" />
+                            <AlertDescription className="break-words">
+                                {editing.lastError}
+                            </AlertDescription>
+                        </Alert>
+                    )}
                     <HorizontalTabs
                         clientSide
                         items={[