diff --git a/api/ee/src/core/entitlements/types.py b/api/ee/src/core/entitlements/types.py
index 791ddfd024..5c09172b6a 100644
--- a/api/ee/src/core/entitlements/types.py
+++ b/api/ee/src/core/entitlements/types.py
@@ -61,8 +61,8 @@ class Probe(BaseModel):
         },
         "features": [
             "2 prompts",
-            "5k traces/month",
             "20 evaluations/month",
+            "5k traces/month",
             "2 seats",
         ],
     },
@@ -109,44 +109,66 @@ class Probe(BaseModel):
         },
         "features": [
             "Unlimited prompts",
-            "10k traces/month",
             "Unlimited evaluations",
-            "3 seats included",
+            "10k free traces/month",
+            "3 free seats",
             "Up to 10 seats",
         ],
     },
-    # {
-    #     "title": "Business",
-    #     "description": "For scale, security, and support.",
-    #     "type": "standard",
-    #     "price": {
-    #         "base": {
-    #             "type": "flat",
-    #             "currency": "USD",
-    #             "amount": 399.00,
-    #             "starting_at": True,
-    #         },
-    #     },
-    #     "features": [
-    #         "Unlimited prompts",
-    #         "Unlimited traces",
-    #         "Unlimited evaluations",
-    #         "Unlimited seats",
-    #     ],
-    # },
     {
-        "title": "Enterprise",
-        "description": "For large organizations or custom needs.",
+        "title": "Business",
+        "description": "For scale, security, and support.",
         "type": "standard",
+        "plan": Plan.CLOUD_V0_BUSINESS.value,
+        "price": {
+            "base": {
+                "type": "flat",
+                "currency": "USD",
+                "amount": 399.00,
+            },
+            "traces": {
+                "type": "tiered",
+                "currency": "USD",
+                "tiers": [
+                    {
+                        "limit": 1_000_000,
+                        "amount": 0.00,
+                    },
+                    {
+                        "amount": 5.00,
+                        "rate": 10_000,
+                    },
+                ],
+            },
+        },
         "features": [
             "Everything in Pro",
             "Unlimited seats",
+            "1M free traces/month",
+            "Multiple workspaces [soon]",
+            "Roles and RBAC",
+            "SSO and MFA [soon]",
             "SOC 2 reports",
+            "HIPAA BAA [soon]",
+            "Private Slack Channel",
+            "Business SLA",
+        ],
+    },
+    {
+        "title": "Enterprise",
+        "description": "For large organizations or custom needs.",
+        "type": "standard",
+        "features": [
+            "Everything in Business",
+            "Custom roles",
+            "Enterprise SSO",
+            "Audit logs",
+            "Self-hosting options",
+            "Bring Your Own Cloud (BYOC)",
             "Security reviews",
             "Dedicated support",
-            "Custom SLAs",
+            "Custom SLA",
             "Custom terms",
-            "Self-hosted deployment options",
         ],
     },
     {
@@ -207,6 +229,20 @@ class Probe(BaseModel):
             Gauge.APPLICATIONS: Quota(strict=True),
         },
     },
+    Plan.CLOUD_V0_BUSINESS: {
+        Tracker.FLAGS: {
+            Flag.HOOKS: True,
+            Flag.RBAC: True,
+        },
+        Tracker.COUNTERS: {
+            Counter.TRACES: Quota(monthly=True, free=1_000_000),
+            Counter.EVALUATIONS: Quota(monthly=True, strict=True),
+        },
+        Tracker.GAUGES: {
+            Gauge.USERS: Quota(strict=True),
+            Gauge.APPLICATIONS: Quota(strict=True),
+        },
+    },
     Plan.CLOUD_V0_HUMANITY_LABS: {
         Tracker.FLAGS: {
             Flag.HOOKS: True,
diff --git a/api/ee/src/core/subscriptions/types.py b/api/ee/src/core/subscriptions/types.py
index 1f55dbe386..719133b654 100644
--- a/api/ee/src/core/subscriptions/types.py
+++ b/api/ee/src/core/subscriptions/types.py
@@ -11,6 +11,7 @@
 class Plan(str, Enum):
     CLOUD_V0_HOBBY = "cloud_v0_hobby"
     CLOUD_V0_PRO = "cloud_v0_pro"
+    CLOUD_V0_BUSINESS = "cloud_v0_business"
     #
     CLOUD_V0_HUMANITY_LABS = "cloud_v0_humanity_labs"
     CLOUD_V0_X_LABS = "cloud_v0_x_labs"
diff --git a/api/pyproject.toml b/api/pyproject.toml
index 5a43a2867a..241f316ffc 100644
--- a/api/pyproject.toml
+++ b/api/pyproject.toml
@@ -1,6 +1,6 @@
 [project]
 name = "api"
-version = "0.59.2"
+version = "0.59.3"
 description = "Agenta API"
 authors = [
     { name = "Mahmoud Mabrouk", email = "mahmoud@agenta.ai" },
diff --git a/sdk/pyproject.toml b/sdk/pyproject.toml
index c86fc0947d..fd19935298 100644
--- a/sdk/pyproject.toml
+++ b/sdk/pyproject.toml
@@ -1,6 +1,6 @@
 [tool.poetry]
 name = "agenta"
-version = "0.59.2"
+version = "0.59.3"
 description = "The SDK for agenta is an open-source LLMOps platform."
 readme = "README.md"
 authors = [
diff --git a/web/ee/package.json b/web/ee/package.json
index ed70a8d15a..983b7d62b2 100644
--- a/web/ee/package.json
+++ b/web/ee/package.json
@@ -1,6 +1,6 @@
 {
     "name": "@agenta/ee",
-    "version": "0.59.2",
+    "version": "0.59.3",
     "private": true,
     "engines": {
         "node": ">=18"
diff --git a/web/ee/src/components/pages/settings/Billing/Modals/PricingModal/assets/PricingCard/index.tsx b/web/ee/src/components/pages/settings/Billing/Modals/PricingModal/assets/PricingCard/index.tsx
index 31d60e6dda..0c9f98ba30 100644
--- a/web/ee/src/components/pages/settings/Billing/Modals/PricingModal/assets/PricingCard/index.tsx
+++ b/web/ee/src/components/pages/settings/Billing/Modals/PricingModal/assets/PricingCard/index.tsx
@@ -8,14 +8,25 @@ import {PricingCardProps} from "../types"
 
 const PricingCard = ({plan, currentPlan, onOptionClick, isLoading}: PricingCardProps) => {
     const _isLoading = isLoading === plan.plan
-    const isDisabled = useMemo(
-        () =>
-            (isLoading !== null && isLoading !== plan.plan) ||
-            currentPlan?.plan == plan.plan ||
-            currentPlan?.plan == Plan.Business ||
-            currentPlan?.plan == Plan.Enterprise,
-        [isLoading, currentPlan, plan],
-    )
+    const isDisabled = useMemo(() => {
+        if (isLoading !== null && isLoading !== plan.plan) {
+            return true
+        }
+
+        if (currentPlan?.plan === plan.plan) {
+            return true
+        }
+
+        if (currentPlan?.plan === Plan.Enterprise) {
+            return true
+        }
+
+        if (currentPlan?.plan === Plan.Business && plan.plan === Plan.Pro) {
+            return true
+        }
+
+        return false
+    }, [isLoading, currentPlan?.plan, plan.plan])
 
     return (
         <Card
@@ -30,23 +41,16 @@ const PricingCard = ({plan, currentPlan, onOptionClick, isLoading}: PricingCardP
             }}
             rootClassName="flex flex-col justify-between"
             actions={[
-                plan.title == "Enterprise" || plan.title == "Business" ? (
+                plan.title == "Enterprise" ? (
                     <Button
                         disabled={isDisabled}
                         className="w-full"
-                        type={
-                            currentPlan?.plan == Plan.Business ||
-                            currentPlan?.plan == Plan.Enterprise
-                                ? "link"
-                                : "primary"
-                        }
+                        type={currentPlan?.plan == Plan.Enterprise ? "link" : "primary"}
                         onClick={() =>
                             window.open("https://cal.com/mahmoud-mabrouk-ogzgey/demo", "_blank")
                         }
                     >
-                        {currentPlan?.plan == Plan.Business || currentPlan?.plan == Plan.Enterprise
-                            ? "Current plan"
-                            : "Talk to us"}
+                        {currentPlan?.plan == Plan.Enterprise ? "Current plan" : "Talk to us"}
                     </Button>
                 ) : (
                     <Button
@@ -54,7 +58,13 @@ const PricingCard = ({plan, currentPlan, onOptionClick, isLoading}: PricingCardP
                         loading={_isLoading}
                         className="w-full"
                         onClick={() => onOptionClick(plan)}
-                        type={currentPlan?.plan === plan.plan ? "link" : "default"}
+                        type={
+                            currentPlan?.plan === plan.plan
+                                ? "link"
+                                : plan.plan === Plan.Hobby
+                                  ? "text"
+                                  : "default"
+                        }
                     >
                         {currentPlan?.plan === plan.plan
                             ? "Current plan"
@@ -79,7 +89,7 @@ const PricingCard = ({plan, currentPlan, onOptionClick, isLoading}: PricingCardP
                     </Typography.Text>
                 </div>
 
-                <ul className="-ml-5">
+                <ul className="-ml-5 overflow-auto">
                     {plan.features?.map((point, idx) => {
                         return (
                             <li className="text-[#586673]" key={idx}>
diff --git a/web/ee/src/components/pages/settings/Billing/Modals/PricingModal/assets/PricingModalContent/index.tsx b/web/ee/src/components/pages/settings/Billing/Modals/PricingModal/assets/PricingModalContent/index.tsx
index 12a1aad499..4c391361af 100644
--- a/web/ee/src/components/pages/settings/Billing/Modals/PricingModal/assets/PricingModalContent/index.tsx
+++ b/web/ee/src/components/pages/settings/Billing/Modals/PricingModal/assets/PricingModalContent/index.tsx
@@ -7,6 +7,7 @@ import {getEnv} from "@/oss/lib/helpers/dynamicEnv"
 import {Plan} from "@/oss/lib/Types"
 import {
     checkoutNewSubscription,
+    switchSubscription,
     usePricingPlans,
     useSubscriptionData,
     useUsageData,
@@ -35,13 +36,15 @@ const PricingModalContent = ({onCancelSubscription, onCloseModal}: PricingModalC
                 if (plan.plan === Plan.Hobby && subscription?.plan !== Plan.Hobby) {
                     onCancelSubscription()
                     return
-                } else {
+                } else if (!subscription || subscription?.plan === Plan.Hobby) {
                     const data = await checkoutNewSubscription({
                         plan: plan.plan,
                         success_url: `${getEnv("NEXT_PUBLIC_AGENTA_WEB_URL")}${projectURL || ""}/settings?tab=billing`,
                     })
 
                     window.open(data.data.checkout_url, "_blank")
+                } else {
+                    await switchSubscription({plan: plan.plan})
                 }
 
                 setTimeout(() => {
@@ -60,6 +63,7 @@ const PricingModalContent = ({onCancelSubscription, onCloseModal}: PricingModalC
         [
             onCancelSubscription,
             checkoutNewSubscription,
+            switchSubscription,
             mutateSubscription,
             mutateUsage,
             projectURL,
diff --git a/web/ee/src/components/pages/settings/Billing/Modals/PricingModal/index.tsx b/web/ee/src/components/pages/settings/Billing/Modals/PricingModal/index.tsx
index ace1e472be..bd92e269f4 100644
--- a/web/ee/src/components/pages/settings/Billing/Modals/PricingModal/index.tsx
+++ b/web/ee/src/components/pages/settings/Billing/Modals/PricingModal/index.tsx
@@ -11,7 +11,7 @@ const PricingModal = ({onCancelSubscription, ...props}: PricingModalProps) => {
     return (
         <EnhancedModal
             className={clsx("[&_.ant-modal-close]:top-[19px]", props.className)}
-            width={900}
+            width={1200}
             title={<PricingModalTitle />}
             footer={null}
             {...props}
diff --git a/web/ee/src/components/pages/settings/Billing/index.tsx b/web/ee/src/components/pages/settings/Billing/index.tsx
index c97e905ace..fec538eac0 100644
--- a/web/ee/src/components/pages/settings/Billing/index.tsx
+++ b/web/ee/src/components/pages/settings/Billing/index.tsx
@@ -74,15 +74,14 @@ const Billing = () => {
                         </Typography.Text>
                     )}
 
-                    {subscription?.plan === Plan.Enterprise ||
-                    subscription?.plan === Plan.Business ? (
+                    {subscription?.plan === Plan.Enterprise ? (
                         <Typography.Text className="text-[#586673]">
                             For queries regarding your plan,{" "}
                             <a href="https://cal.com/mahmoud-mabrouk-ogzgey/demo" target="_blank">
                                 click here to contact us
                             </a>
                         </Typography.Text>
-                    ) : subscription?.plan === Plan.Pro ? (
+                    ) : subscription?.plan === Plan.Pro || subscription?.plan === Plan.Business ? (
                         <div className="flex items-center gap-2">
                             <Button type="primary" onClick={() => setIsOpenPricingModal(true)}>
                                 Upgrade plan
diff --git a/web/oss/package.json b/web/oss/package.json
index ad24ead415..2f5082d263 100644
--- a/web/oss/package.json
+++ b/web/oss/package.json
@@ -1,6 +1,6 @@
 {
     "name": "@agenta/oss",
-    "version": "0.59.2",
+    "version": "0.59.3",
     "private": true,
     "engines": {
         "node": ">=18"
diff --git a/web/oss/src/components/Playground/Components/PlaygroundTool/index.tsx b/web/oss/src/components/Playground/Components/PlaygroundTool/index.tsx
index 57301b78f2..c190f64f9e 100644
--- a/web/oss/src/components/Playground/Components/PlaygroundTool/index.tsx
+++ b/web/oss/src/components/Playground/Components/PlaygroundTool/index.tsx
@@ -21,29 +21,32 @@ const PlaygroundTool = ({value, disabled, variantId, baseProperty, ...editorProp
     const editorIdRef = useRef(uuidv4())
     const isReadOnly = Boolean(disabled)
     const [minimized, setMinimized] = useState(false)
-    const [toolString, setToolString] = useState(() => {
+    const [toolString, setToolString] = useState<string | null>(() => {
         try {
-            return typeof value === "string" ? value : JSON5.stringify(value)
+            if (!value) {
+                return ""
+            }
+            return typeof value === "string" ? value : JSON5.stringify(value, null, 2)
         } catch (e) {
-            return null
+            return ""
         }
     })
     const [functionName, setFunctionName] = useState(() => {
         try {
             return typeof value === "string"
-                ? JSON5.parse(value)?.function?.name
-                : value?.function?.name
+                ? (JSON5.parse(value)?.function?.name ?? "")
+                : (value?.function?.name ?? "")
         } catch (err) {
-            return null
+            return ""
         }
     })
     const [functionDescription, setFunctionDescription] = useState(() => {
         try {
             return typeof value === "string"
-                ? JSON5.parse(value)?.function?.description
-                : value?.function?.description
+                ? (JSON5.parse(value)?.function?.description ?? "")
+                : (value?.function?.description ?? "")
         } catch (err) {
-            return null
+            return ""
         }
     })
 
@@ -56,79 +59,85 @@ const PlaygroundTool = ({value, disabled, variantId, baseProperty, ...editorProp
         }
     }, [toolString])
 
-    useEffect(() => {
-        if (isReadOnly || !toolString) {
-            return
-        }
+    const syncToolFunctionField = useCallback(
+        (updater: (toolFunction: any) => any) => {
+            if (isReadOnly) return
 
-        try {
-            const toolObj = JSON5.parse(toolString)
-            if (toolObj && toolObj.function) {
-                toolObj.function.name = functionName
-            }
-            setToolString(JSON.stringify(toolObj))
-        } catch (err) {
-            console.error(err)
-        }
-    }, [functionName, isReadOnly, toolString])
+            setToolString((currentString) => {
+                if (!currentString) return currentString
 
-    useEffect(() => {
-        if (isReadOnly || !toolString) {
-            return
-        }
+                try {
+                    const parsedTool = JSON5.parse(currentString)
+                    const currentFunction = parsedTool.function ?? {}
+                    const nextFunction = updater(currentFunction)
+                    const isSameReference =
+                        (parsedTool.function && nextFunction === parsedTool.function) ||
+                        nextFunction === currentFunction
+                    const nextFunctionIsObject =
+                        typeof nextFunction === "object" && nextFunction !== null
+                    const isEmptyNoop =
+                        !parsedTool.function &&
+                        nextFunction === currentFunction &&
+                        (!nextFunctionIsObject || Object.keys(nextFunction).length === 0)
 
-        try {
-            const toolObj = JSON5.parse(toolString)
-            if (toolObj && toolObj.function) {
-                toolObj.function.description = functionDescription
-            }
+                    if (isSameReference || isEmptyNoop) {
+                        return currentString
+                    }
 
-            setToolString(JSON.stringify(toolObj))
-        } catch (err) {
-            console.error(err)
-        }
-    }, [functionDescription, isReadOnly, toolString])
+                    const updatedTool = {
+                        ...parsedTool,
+                        function: nextFunction,
+                    }
+
+                    const nextString = JSON.stringify(updatedTool, null, 2)
+                    return nextString === currentString ? currentString : nextString
+                } catch (err) {
+                    console.error(err)
+                    return currentString
+                }
+            })
+        },
+        [isReadOnly],
+    )
 
     useEffect(() => {
         if (isReadOnly) return
-
         try {
             const parsedTool = JSON5.parse(toolString)
             editorProps?.handleChange?.(parsedTool)
             setFunctionName((currentName) => {
-                if (currentName !== parsedTool?.function?.name) {
-                    return parsedTool?.function?.name
+                const nextName = parsedTool?.function?.name ?? ""
+                if (currentName !== nextName) {
+                    return nextName
                 }
                 return currentName
             })
             setFunctionDescription((currentDescription) => {
-                if (currentDescription !== parsedTool?.function?.description) {
-                    return parsedTool?.function?.description
+                const nextDescription = parsedTool?.function?.description ?? ""
+                if (currentDescription !== nextDescription) {
+                    return nextDescription
                 }
                 return currentDescription
             })
         } catch (e) {
             if (!toolString) {
-                setFunctionName(null)
-                setFunctionDescription(null)
+                setFunctionName("")
+                setFunctionDescription("")
             }
         }
     }, [toolString, isReadOnly])
-
     // Use atom-based state management for direct prompt updates via derived prompts
     const variant = useAtomValue(variantByRevisionIdAtomFamily(variantId)) as any
     const appUriInfo = useAtomValue(appUriInfoAtom)
     const setPrompts = useSetAtom(
         useMemo(() => promptsAtomFamily(variantId), [variant, variantId, appUriInfo?.routePath]),
     )
-
     const deleteMessage = useCallback(() => {
         if (isReadOnly) return
         if (!baseProperty?.__id) {
             console.warn("Cannot delete tool: tool property ID not found")
             return
         }
-
         setPrompts((prevPrompts: any[] = []) => {
             return prevPrompts.map((prompt: any) => {
                 const toolsArr = prompt?.llmConfig?.tools?.value
@@ -153,7 +162,6 @@ const PlaygroundTool = ({value, disabled, variantId, baseProperty, ...editorProp
             })
         })
     }, [isReadOnly, variantId, baseProperty?.__id, setPrompts])
-
     return (
         <PlaygroundVariantPropertyControlWrapper
             className={clsx(
@@ -171,7 +179,7 @@ const PlaygroundTool = ({value, disabled, variantId, baseProperty, ...editorProp
                 id={editorIdRef.current}
             >
                 <SharedEditor
-                    initialValue={toolString}
+                    initialValue={toolString ?? ""}
                     editorProps={{
                         codeOnly: true,
                         noProvider: true,
@@ -181,6 +189,7 @@ const PlaygroundTool = ({value, disabled, variantId, baseProperty, ...editorProp
                         if (isReadOnly) return
                         setToolString(e)
                     }}
+                    syncWithInitialValueChanges
                     editorType="border"
                     className={clsx([
                         "mt-2",
@@ -209,10 +218,21 @@ const PlaygroundTool = ({value, disabled, variantId, baseProperty, ...editorProp
                                             variant="borderless"
                                             placeholder="Function Name"
                                             disabled={isReadOnly || !parsed}
-                                            // onChange={handleNameChange}
                                             onChange={(e) => {
                                                 if (isReadOnly) return
-                                                setFunctionName(e.target.value)
+
+                                                const nextName = e.target.value
+                                                setFunctionName(nextName)
+                                                syncToolFunctionField((toolFunction) => {
+                                                    if (toolFunction?.name === nextName) {
+                                                        return toolFunction
+                                                    }
+
+                                                    return {
+                                                        ...toolFunction,
+                                                        name: nextName,
+                                                    }
+                                                })
                                             }}
                                         />
                                     </Tooltip>
@@ -230,10 +250,24 @@ const PlaygroundTool = ({value, disabled, variantId, baseProperty, ...editorProp
                                             variant="borderless"
                                             placeholder="Function Description"
                                             disabled={isReadOnly || !parsed}
-                                            // onChange={handleDescriptionChange}
                                             onChange={(e) => {
                                                 if (isReadOnly) return
-                                                setFunctionDescription(e.target.value)
+
+                                                const nextDescription = e.target.value
+                                                setFunctionDescription(nextDescription)
+                                                syncToolFunctionField((toolFunction) => {
+                                                    if (
+                                                        toolFunction?.description ===
+                                                        nextDescription
+                                                    ) {
+                                                        return toolFunction
+                                                    }
+
+                                                    return {
+                                                        ...toolFunction,
+                                                        description: nextDescription,
+                                                    }
+                                                })
                                             }}
                                         />
                                     </Tooltip>
diff --git a/web/oss/src/components/Playground/Components/SharedEditor/index.tsx b/web/oss/src/components/Playground/Components/SharedEditor/index.tsx
index 87aa9e2957..2f6c415593 100644
--- a/web/oss/src/components/Playground/Components/SharedEditor/index.tsx
+++ b/web/oss/src/components/Playground/Components/SharedEditor/index.tsx
@@ -31,12 +31,15 @@ const SharedEditor = ({
     propertyId,
     baseProperty,
     variantId,
+    syncWithInitialValueChanges = false,
     ...props
 }: SharedEditorProps) => {
+    const normalizedInitialValue = initialValue ?? ""
+
     const [isEditorFocused, setIsEditorFocused] = useState(false)
 
     const [localValue, setLocalValue] = useDebounceInput<string>(
-        initialValue,
+        normalizedInitialValue,
         handleChange,
         300,
         "",
@@ -56,7 +59,11 @@ const SharedEditor = ({
     )
     const editorId = editorIdRef.current
 
-    const mountInitialValueRef = useRef<string>(initialValue)
+    const mountInitialValueRef = useRef<string>(normalizedInitialValue)
+
+    if (syncWithInitialValueChanges) {
+        mountInitialValueRef.current = normalizedInitialValue
+    }
 
     return (
         <div
diff --git a/web/oss/src/components/Playground/Components/SharedEditor/types.d.ts b/web/oss/src/components/Playground/Components/SharedEditor/types.d.ts
index 566f99535e..58353f3cdf 100644
--- a/web/oss/src/components/Playground/Components/SharedEditor/types.d.ts
+++ b/web/oss/src/components/Playground/Components/SharedEditor/types.d.ts
@@ -21,4 +21,6 @@ export interface SharedEditorProps extends BaseContainerProps {
     debug?: boolean
     isTool?: boolean
     handleChange?: (value: string) => void
+
+    syncWithInitialValueChanges?: boolean
 }
diff --git a/web/oss/src/components/pages/observability/drawer/TraceContent/utils/index.ts b/web/oss/src/components/pages/observability/drawer/TraceContent/utils/index.ts
index 68c841b324..4664ec4e71 100644
--- a/web/oss/src/components/pages/observability/drawer/TraceContent/utils/index.ts
+++ b/web/oss/src/components/pages/observability/drawer/TraceContent/utils/index.ts
@@ -1,25 +1,32 @@
 export const transformDataInputs = (data: any) => {
-    return Object.keys(data).reduce((acc, curr) => {
-        if (curr === "prompt") {
-            acc[curr] = data[curr]
-        }
-
-        if (!acc.tools) {
-            acc.tools = []
-        }
-
-        if (curr === "functions") {
-            const functions = data[curr].map((item: any) => ({
-                type: "function",
-                function: item,
-            }))
-            acc.tools.push(...functions)
-        }
-
-        if (curr === "tools") {
-            acc.tools.push(...data[curr])
-        }
-
-        return acc
-    }, {} as any)
+    if (!data) {
+        return {}
+    }
+
+    const transformed: Record<string, any> = {}
+
+    if (data.prompt) {
+        transformed.prompt = data.prompt
+    }
+
+    const tools: any[] = []
+
+    if (Array.isArray(data.functions)) {
+        const functions = data.functions.map((item: any) => ({
+            type: "function",
+            function: item,
+        }))
+
+        tools.push(...functions)
+    }
+
+    if (Array.isArray(data.tools)) {
+        tools.push(...data.tools)
+    }
+
+    if (tools.length > 0) {
+        transformed.tools = tools
+    }
+
+    return transformed
 }
diff --git a/web/oss/src/components/pages/observability/drawer/TraceSidePanel/TraceAnnotations/index.tsx b/web/oss/src/components/pages/observability/drawer/TraceSidePanel/TraceAnnotations/index.tsx
index de40518d82..8a14a46ef2 100644
--- a/web/oss/src/components/pages/observability/drawer/TraceSidePanel/TraceAnnotations/index.tsx
+++ b/web/oss/src/components/pages/observability/drawer/TraceSidePanel/TraceAnnotations/index.tsx
@@ -1,4 +1,4 @@
-import React, {useState} from "react"
+import React, {useMemo, useState} from "react"
 
 import {CloseOutlined} from "@ant-design/icons"
 import {Button, Popover, Space, Typography} from "antd"
@@ -17,91 +17,228 @@ interface TraceAnnotationsProps {
     annotations: AnnotationDto[]
 }
 
+type AnnotationCategory = "metric" | "note" | "extra"
+
+type AnnotationChipEntry = {
+    annotations: {value: any; user: string}[]
+    average?: number
+    category: AnnotationCategory
+}
+
 const TraceAnnotations = ({annotations}: TraceAnnotationsProps) => {
     const classes = useStyles()
     const [isAnnotationsPopoverOpen, setIsAnnotationsPopoverOpen] = useState<string | null>(null)
     const getPopoverKey = (refId: string, key: string) => `${refId}-${key}`
-    const grouped = groupAnnotationsByReferenceId(annotations)
+    const grouped = useMemo(() => {
+        const groupedMetrics = groupAnnotationsByReferenceId(annotations)
+        const result: Record<string, Record<string, AnnotationChipEntry>> = {}
+
+        for (const [refId, metrics] of Object.entries(groupedMetrics)) {
+            result[refId] = {}
+
+            for (const [metricName, metricValue] of Object.entries(metrics)) {
+                result[refId][metricName] = {
+                    annotations: (metricValue.annotations || []) as {value: any; user: string}[],
+                    average: metricValue.average,
+                    category: "metric",
+                }
+            }
+        }
+
+        for (const annotation of annotations) {
+            const refId = annotation.references?.evaluator?.slug
+            if (!refId) continue
+
+            if (!result[refId]) {
+                result[refId] = {}
+            }
+
+            const outputs = (annotation.data?.outputs || {}) as Record<string, any>
+            const categories: Array<[AnnotationCategory, Record<string, any>]> = [
+                ["note", outputs.notes || {}],
+                ["extra", outputs.extra || {}],
+            ]
+
+            for (const [category, values] of categories) {
+                for (const [key, value] of Object.entries(values)) {
+                    if (value === undefined || value === null) continue
+
+                    if (!result[refId][key]) {
+                        result[refId][key] = {
+                            annotations: [],
+                            category,
+                        }
+                    }
+
+                    result[refId][key].annotations.push({
+                        value,
+                        user: annotation.createdBy || "",
+                    })
+                }
+            }
+        }
+
+        return result
+    }, [annotations])
+
+    const hasAnnotations = useMemo(
+        () =>
+            Object.values(grouped).some((group) =>
+                Object.values(group).some((entry) => entry.annotations.length > 0),
+            ),
+        [grouped],
+    )
 
-    return Object.entries(grouped).length > 0 ? (
+    const getSummaryValue = (metric: AnnotationChipEntry) => {
+        if (metric.category === "metric") {
+            // const values = metric.annotations.map((item) => item.value)
+            // const allBooleans = values.every((value) => typeof value === "boolean")
+
+            // if (allBooleans) {
+            //     const trueCount = values.filter(Boolean).length
+            //     const percentage = Math.round((trueCount / values.length) * 100)
+            //     return `${percentage}% true`
+            // }
+
+            if (metric.average !== undefined) {
+                return `μ ${metric.average}`
+            }
+        }
+
+        const uniqueValues = Array.from(
+            new Set(
+                metric.annotations
+                    .map((annotation) => {
+                        const rawValue = getStringOrJson(annotation.value)
+                        if (typeof rawValue !== "string") return undefined
+                        const singleLine = rawValue.replace(/\s+/g, " ").trim()
+                        return singleLine.length > 0 ? singleLine : undefined
+                    })
+                    .filter((value): value is string => Boolean(value)),
+            ),
+        )
+
+        if (uniqueValues.length === 0) return ""
+        if (uniqueValues.length === 1) return uniqueValues[0]
+
+        return `${uniqueValues.length} values`
+    }
+
+    return hasAnnotations ? (
         <div className="flex flex-col gap-3">
-            {Object.entries(grouped).map(([refId, metricsArr], index) => {
-                const filteredMetrics = Object.entries(metricsArr).filter(
-                    ([, metric]) => metric.average !== undefined,
-                )
+            {Object.entries(grouped).map(([refId, metricsArr]) => {
+                const filteredMetrics = Object.entries(metricsArr)
+                    .filter(([, metric]) => metric.annotations.length > 0)
+                    .sort(([a], [b]) => a.localeCompare(b))
 
                 if (filteredMetrics.length === 0) return null
 
                 return (
-                    <div key={index} className="flex flex-col gap-[6px]">
+                    <div key={refId} className="flex flex-col gap-[6px]">
                         <Typography.Text type="secondary" className="text-[10px]">
                             {refId}
                         </Typography.Text>
 
-                        {filteredMetrics.map(([key, metric], index) => (
-                            <div key={index}>
-                                <Popover
-                                    overlayClassName={classes.annotationPopover}
-                                    open={isAnnotationsPopoverOpen === getPopoverKey(refId, key)}
-                                    onOpenChange={(open) => {
-                                        setIsAnnotationsPopoverOpen(
-                                            open ? getPopoverKey(refId, key) : null,
-                                        )
-                                    }}
-                                    placement="bottom"
-                                    trigger="click"
-                                    arrow={false}
-                                    title={
-                                        <div className="flex items-center justify-between">
-                                            <Space className="truncate overflow-hidden">
-                                                <Typography.Text>Total mean:</Typography.Text>
-                                                <CustomAntdTag
-                                                    value={`μ ${metric.average}`}
-                                                    bordered={false}
-                                                />
-                                            </Space>
-                                            <Button
-                                                type="text"
-                                                icon={<CloseOutlined />}
-                                                onClick={() => setIsAnnotationsPopoverOpen(null)}
+                        {filteredMetrics.map(([key, metric]) => {
+                            const summaryValue = getSummaryValue(metric)
+                            const popoverTitle =
+                                metric.category === "metric" && metric.average !== undefined ? (
+                                    <div className="flex items-center justify-between">
+                                        <Space className="truncate overflow-hidden">
+                                            <Typography.Text>Total mean:</Typography.Text>
+                                            <CustomAntdTag
+                                                value={`μ ${metric.average}`}
+                                                bordered={false}
                                             />
+                                        </Space>
+                                        <Button
+                                            type="text"
+                                            icon={<CloseOutlined />}
+                                            onClick={() => setIsAnnotationsPopoverOpen(null)}
+                                        />
+                                    </div>
+                                ) : (
+                                    <div className="flex items-center justify-between gap-2">
+                                        <div className="flex flex-col overflow-hidden">
+                                            <Typography.Text className="truncate">
+                                                {key}
+                                            </Typography.Text>
+                                            {summaryValue ? (
+                                                <Typography.Text
+                                                    type="secondary"
+                                                    className="truncate"
+                                                >
+                                                    {summaryValue}
+                                                </Typography.Text>
+                                            ) : null}
                                         </div>
-                                    }
-                                    content={
-                                        <div className="flex flex-col gap-2">
-                                            {metric.annotations?.map(
-                                                (annotation: any, i: number) => (
-                                                    <Space
-                                                        className="items-center justify-between"
-                                                        key={i}
-                                                    >
-                                                        <UserAvatarTag
-                                                            modifiedBy={annotation.user || ""}
-                                                        />
-                                                        <Typography.Text type="secondary">
-                                                            {getStringOrJson(annotation.value)}
-                                                        </Typography.Text>
-                                                    </Space>
-                                                ),
+                                        <Button
+                                            type="text"
+                                            icon={<CloseOutlined />}
+                                            onClick={() => setIsAnnotationsPopoverOpen(null)}
+                                        />
+                                    </div>
+                                )
+
+                            return (
+                                <div key={key}>
+                                    <Popover
+                                        overlayClassName={classes.annotationPopover}
+                                        open={
+                                            isAnnotationsPopoverOpen === getPopoverKey(refId, key)
+                                        }
+                                        onOpenChange={(open) => {
+                                            setIsAnnotationsPopoverOpen(
+                                                open ? getPopoverKey(refId, key) : null,
+                                            )
+                                        }}
+                                        placement="bottom"
+                                        trigger="click"
+                                        arrow={false}
+                                        title={popoverTitle}
+                                        content={
+                                            <div className="flex flex-col gap-2">
+                                                {metric.annotations?.map(
+                                                    (annotation: any, i: number) => (
+                                                        <Space
+                                                            className="items-center justify-between"
+                                                            key={i}
+                                                        >
+                                                            <UserAvatarTag
+                                                                modifiedBy={annotation.user || ""}
+                                                            />
+                                                            <Typography.Text type="secondary">
+                                                                {getStringOrJson(annotation.value)}
+                                                            </Typography.Text>
+                                                        </Space>
+                                                    ),
+                                                )}
+                                            </div>
+                                        }
+                                    >
+                                        <div
+                                            className={clsx(
+                                                "flex items-center flex-wrap gap-2 justify-between",
+                                                "py-1 px-3 cursor-pointer",
+                                                "rounded-lg border border-[#BDC7D1] border-solid",
                                             )}
+                                        >
+                                            <Typography.Text className="truncate overflow-hidden text-ellipsis flex-1">
+                                                {key}
+                                            </Typography.Text>
+                                            {summaryValue ? (
+                                                <Typography.Text
+                                                    type="secondary"
+                                                    className="truncate overflow-hidden text-ellipsis"
+                                                >
+                                                    {summaryValue}
+                                                </Typography.Text>
+                                            ) : null}
                                         </div>
-                                    }
-                                >
-                                    <div
-                                        className={clsx(
-                                            "flex items-center flex-wrap gap-2 justify-between",
-                                            "py-1 px-3 cursor-pointer",
-                                            "rounded-lg border border-[#BDC7D1] border-solid",
-                                        )}
-                                    >
-                                        <Typography.Text className="truncate overflow-hidden text-ellipsis flex-1">
-                                            {key}
-                                        </Typography.Text>
-                                        <Typography.Text type="secondary">{`μ ${metric.average}`}</Typography.Text>
-                                    </div>
-                                </Popover>
-                            </div>
-                        ))}
+                                    </Popover>
+                                </div>
+                            )
+                        })}
                     </div>
                 )
             })}
diff --git a/web/oss/src/lib/helpers/analytics/AgPosthogProvider.tsx b/web/oss/src/lib/helpers/analytics/AgPosthogProvider.tsx
index 35111d5d25..7fd52ec58e 100644
--- a/web/oss/src/lib/helpers/analytics/AgPosthogProvider.tsx
+++ b/web/oss/src/lib/helpers/analytics/AgPosthogProvider.tsx
@@ -1,4 +1,4 @@
-import {useCallback, useEffect, useState} from "react"
+import {useCallback, useEffect, useRef, useState} from "react"
 
 import {useAtom} from "jotai"
 import {useRouter} from "next/router"
@@ -10,14 +10,18 @@ import {CLOUD_CONFIG, OSS_CONFIG} from "./assets/constants"
 import {posthogAtom, type PostHogConfig} from "./store/atoms"
 import {CustomPosthogProviderType} from "./types"
 
+const MAX_POSTHOG_INIT_ATTEMPTS = 3
+
 const CustomPosthogProvider: CustomPosthogProviderType = ({children}) => {
     const router = useRouter()
     const [loadingPosthog, setLoadingPosthog] = useState(false)
     const [posthogClient, setPosthogClient] = useAtom(posthogAtom)
+    const failedAttemptsRef = useRef(0)
 
     const initPosthog = useCallback(async () => {
         if (posthogClient) return
         if (loadingPosthog) return
+        if (failedAttemptsRef.current >= MAX_POSTHOG_INIT_ATTEMPTS) return
         if (!getEnv("NEXT_PUBLIC_POSTHOG_API_KEY")) return
 
         setLoadingPosthog(true)
@@ -32,11 +36,17 @@ const CustomPosthogProvider: CustomPosthogProviderType = ({children}) => {
                 // Enable debug mode in development
                 loaded: (posthog) => {
                     setPosthogClient(posthog)
+                    failedAttemptsRef.current = 0
                     if (process.env.NODE_ENV === "development") posthog.debug()
                 },
                 capture_pageview: false,
                 ...((isDemo() ? CLOUD_CONFIG : OSS_CONFIG) as Partial<PostHogConfig>),
             })
+        } catch (error) {
+            failedAttemptsRef.current += 1
+            if (failedAttemptsRef.current >= MAX_POSTHOG_INIT_ATTEMPTS) {
+                console.warn("PostHog failed to initialize after maximum attempts", error)
+            }
         } finally {
             setLoadingPosthog(false)
         }
diff --git a/web/oss/src/lib/helpers/observability_helpers.ts b/web/oss/src/lib/helpers/observability_helpers.ts
index d0939dfdfe..b02ed174a4 100644
--- a/web/oss/src/lib/helpers/observability_helpers.ts
+++ b/web/oss/src/lib/helpers/observability_helpers.ts
@@ -8,6 +8,7 @@ import {
 
 import {uuidToSpanId, uuidToTraceId} from "../hooks/useAnnotations/assets/helpers"
 import {TraceSpanNode} from "@/oss/services/tracing/types"
+import {sortSpansByStartTime} from "./tracing"
 
 const normalizeContentFields = (obj: any): void => {
     if (Array.isArray(obj)) {
@@ -59,7 +60,7 @@ export const observabilityTransformer = (
     }
 
     if (item.nodes) {
-        return Object.entries(item.nodes)
+        const children = Object.entries(item.nodes)
             .flatMap(([_, value]) => {
                 if (Array.isArray(value)) {
                     return value.map((childNode, index) =>
@@ -73,6 +74,9 @@ export const observabilityTransformer = (
                 }
             })
             .filter((node): node is _AgentaRootsResponse => node !== null && node !== undefined)
+
+        // Sort children at this hierarchy level by start_time
+        return sortSpansByStartTime(children)
     }
 
     return []
diff --git a/web/oss/src/lib/helpers/tracing.ts b/web/oss/src/lib/helpers/tracing.ts
new file mode 100644
index 0000000000..8b0340fa50
--- /dev/null
+++ b/web/oss/src/lib/helpers/tracing.ts
@@ -0,0 +1,41 @@
+/**
+ * Sorts an array of spans by their start_time in ascending order (earliest first).
+ *
+ * This function ensures hierarchical tree structures display spans in chronological order.
+ * It only sorts spans at the same level - parent/child relationships are maintained.
+ *
+ * Sorting logic:
+ * - Primary: start_time (ascending - earliest first)
+ * - Secondary: span_id (for concurrent spans with identical start times)
+ * - Spans without start_time are placed at the end
+ *
+ * @param spans - Array of spans to sort
+ * @returns New sorted array (does not mutate input)
+ */
+export const sortSpansByStartTime = <T extends { start_time?: string | number; span_id?: string }>(
+    spans: T[],
+): T[] => {
+    return [...spans].sort((a, b) => {
+        const aTime = a.start_time
+        const bTime = b.start_time
+
+        // Handle missing start_time - push to end
+        if (!aTime && !bTime) return 0
+        if (!aTime) return 1
+        if (!bTime) return -1
+
+        // Convert to milliseconds for comparison
+        const aMs = typeof aTime === "number" ? aTime : new Date(aTime).getTime()
+        const bMs = typeof bTime === "number" ? bTime : new Date(bTime).getTime()
+
+        // Primary sort: by start_time
+        if (aMs !== bMs) {
+            return aMs - bMs
+        }
+
+        // Secondary sort: by span_id for concurrent spans
+        const aId = a.span_id || ""
+        const bId = b.span_id || ""
+        return aId.localeCompare(bId)
+    })
+}
diff --git a/web/oss/src/services/tracing/lib/helpers.ts b/web/oss/src/services/tracing/lib/helpers.ts
index ab1bd2e64f..4cf9856eb0 100644
--- a/web/oss/src/services/tracing/lib/helpers.ts
+++ b/web/oss/src/services/tracing/lib/helpers.ts
@@ -1,3 +1,5 @@
+import {sortSpansByStartTime} from "@/oss/lib/helpers/tracing"
+
 import {TraceSpanNode, TracesResponse, SpansResponse} from "../types"
 
 export const isTracesResponse = (data: any): data is TracesResponse => {
@@ -14,7 +16,7 @@ export const transformTracesResponseToTree = (data: TracesResponse): TraceSpanNo
             return []
         }
 
-        return Object.values(spans).flatMap((span: any) => {
+        const spanArray = Object.values(spans).flatMap((span: any) => {
             if (Array.isArray(span)) {
                 return buildTree(span)
             }
@@ -29,6 +31,9 @@ export const transformTracesResponseToTree = (data: TracesResponse): TraceSpanNo
 
             return node
         })
+
+        // Sort spans at this hierarchy level by start_time
+        return sortSpansByStartTime(spanArray)
     }
 
     return Object.values(data.traces).flatMap((trace: any) => buildTree(trace.spans))
diff --git a/web/oss/src/state/newPlayground/chat/actions.ts b/web/oss/src/state/newPlayground/chat/actions.ts
index 360318c445..ef43047222 100644
--- a/web/oss/src/state/newPlayground/chat/actions.ts
+++ b/web/oss/src/state/newPlayground/chat/actions.ts
@@ -128,9 +128,20 @@ export const runChatTurnAtom = atom(
         set,
         params: {turnId: string; variantId?: string; revisions?: string[]; messageId?: string},
     ) => {
-        let {turnId, variantId, revisions, messageId} = params
+        const {turnId, variantId, revisions, messageId} = params
         const displayed = revisions ?? (get(displayedVariantsAtom) || [])
 
+        const ids = (get(chatTurnIdsAtom) || []) as string[]
+        const idx = ids.indexOf(turnId)
+        const isLast = idx >= 0 && idx === ids.length - 1
+        if (!isLast && messageId) {
+            set(chatTurnIdsAtom, (prev) => {
+                const list = prev || []
+                const i = list.indexOf(turnId)
+                return i >= 0 ? list.slice(0, i + 1) : list
+            })
+        }
+
         if (variantId) {
             const rowId = turnId
             // map[variantId] || `turn-${variantId}-${turnId}`
@@ -164,26 +175,10 @@ export const runChatTurnAtom = atom(
 // Runnable means the user message has non-empty text or an image_url with a url
 export const runAllChatAtom = atom(null, (get, set) => {
     const turnIds = (get(chatTurnIdsAtom) || []) as string[]
-    const turnsById = (get(chatTurnsByIdAtom) || {}) as Record<string, any>
     if (!Array.isArray(turnIds) || turnIds.length === 0) return
 
-    // Simple check: non-empty user message (string) or any array content
-    const hasUser = (val: any) => {
-        if (typeof val === "string") return val.trim().length > 0
-        if (Array.isArray(val)) return val.length > 0
-        return false
-    }
-
-    let targetId: string | undefined
-    for (let i = turnIds.length - 1; i >= 0; i--) {
-        const rowId = turnIds[i]
-        const turn = (turnsById as any)[rowId]
-        const val = turn?.userMessage
-        if (val) {
-            targetId = rowId
-            break
-        }
-    }
+    // Always target the last logical turn id.
+    const targetId = turnIds[turnIds.length - 1]
     if (!targetId) return
     set(runChatTurnAtom, {turnId: targetId})
 })
diff --git a/web/package.json b/web/package.json
index af0c25fc88..f5ad245cfa 100644
--- a/web/package.json
+++ b/web/package.json
@@ -1,6 +1,6 @@
 {
     "name": "agenta-web",
-    "version": "0.59.2",
+    "version": "0.59.3",
     "workspaces": [
         "ee",
         "oss",