diff --git a/crates/agent/src/active_thread.rs b/crates/agent/src/active_thread.rs
index 1d15ee6ccb..d04d0cbcb9 100644
--- a/crates/agent/src/active_thread.rs
+++ b/crates/agent/src/active_thread.rs
@@ -1,4 +1,3 @@
-use crate::AgentPanel;
 use crate::context::{AgentContextHandle, RULES_ICON};
 use crate::context_picker::{ContextPicker, MentionLink};
 use crate::context_store::ContextStore;
@@ -13,6 +12,7 @@ use crate::tool_use::{PendingToolUseStatus, ToolUse};
 use crate::ui::{
     AddedContext, AgentNotification, AgentNotificationEvent, AnimatedLabel, ContextPill,
 };
+use crate::{AgentPanel, ModelUsageContext};
 use agent_settings::{AgentSettings, NotifyWhenAgentWaiting};
 use anyhow::Context as _;
 use assistant_tool::ToolUseStatus;
@@ -1348,6 +1348,7 @@ impl ActiveThread {
                 Some(self.text_thread_store.downgrade()),
                 context_picker_menu_handle.clone(),
                 SuggestContextKind::File,
+                ModelUsageContext::Thread(self.thread.clone()),
                 window,
                 cx,
             )
@@ -1826,9 +1827,10 @@ impl ActiveThread {
 
         // Get all the data we need from thread before we start using it in closures
         let checkpoint = thread.checkpoint_for_message(message_id);
+        let configured_model = thread.configured_model().map(|m| m.model);
         let added_context = thread
             .context_for_message(message_id)
-            .map(|context| AddedContext::new_attached(context, cx))
+            .map(|context| AddedContext::new_attached(context, configured_model.as_ref(), cx))
             .collect::<Vec<_>>();
 
         let tool_uses = thread.tool_uses_for_message(message_id, cx);
diff --git a/crates/agent/src/agent.rs b/crates/agent/src/agent.rs
index c847477b18..db458b771e 100644
--- a/crates/agent/src/agent.rs
+++ b/crates/agent/src/agent.rs
@@ -36,7 +36,7 @@ use fs::Fs;
 use gpui::{App, Entity, actions, impl_actions};
 use language::LanguageRegistry;
 use language_model::{
-    ConfiguredModel, LanguageModelId, LanguageModelProviderId, LanguageModelRegistry,
+    ConfiguredModel, LanguageModel, LanguageModelId, LanguageModelProviderId, LanguageModelRegistry,
 };
 use prompt_store::PromptBuilder;
 use schemars::JsonSchema;
@@ -132,6 +132,11 @@ impl ModelUsageContext {
             }
         }
     }
+
+    pub fn language_model(&self, cx: &App) -> Option<Arc<dyn LanguageModel>> {
+        self.configured_model(cx)
+            .map(|configured_model| configured_model.model)
+    }
 }
 
 /// Initializes the `agent` crate.
diff --git a/crates/agent/src/context.rs b/crates/agent/src/context.rs
index 62106e1968..aaf613ea5f 100644
--- a/crates/agent/src/context.rs
+++ b/crates/agent/src/context.rs
@@ -745,6 +745,7 @@ pub struct ImageContext {
 pub enum ImageStatus {
     Loading,
     Error,
+    Warning,
     Ready,
 }
 
@@ -761,11 +762,17 @@ impl ImageContext {
         self.image_task.clone().now_or_never().flatten()
     }
 
-    pub fn status(&self) -> ImageStatus {
+    pub fn status(&self, model: Option<&Arc<dyn language_model::LanguageModel>>) -> ImageStatus {
         match self.image_task.clone().now_or_never() {
             None => ImageStatus::Loading,
             Some(None) => ImageStatus::Error,
-            Some(Some(_)) => ImageStatus::Ready,
+            Some(Some(_)) => {
+                if model.is_some_and(|model| !model.supports_images()) {
+                    ImageStatus::Warning
+                } else {
+                    ImageStatus::Ready
+                }
+            }
         }
     }
 
diff --git a/crates/agent/src/context_strip.rs b/crates/agent/src/context_strip.rs
index f28e61aa82..2de2dcd024 100644
--- a/crates/agent/src/context_strip.rs
+++ b/crates/agent/src/context_strip.rs
@@ -23,7 +23,7 @@ use crate::thread_store::{TextThreadStore, ThreadStore};
 use crate::ui::{AddedContext, ContextPill};
 use crate::{
     AcceptSuggestedContext, AgentPanel, FocusDown, FocusLeft, FocusRight, FocusUp,
-    RemoveAllContext, RemoveFocusedContext, ToggleContextPicker,
+    ModelUsageContext, RemoveAllContext, RemoveFocusedContext, ToggleContextPicker,
 };
 
 pub struct ContextStrip {
@@ -37,6 +37,7 @@ pub struct ContextStrip {
     _subscriptions: Vec<Subscription>,
     focused_index: Option<usize>,
     children_bounds: Option<Vec<Bounds<Pixels>>>,
+    model_usage_context: ModelUsageContext,
 }
 
 impl ContextStrip {
@@ -47,6 +48,7 @@ impl ContextStrip {
         text_thread_store: Option<WeakEntity<TextThreadStore>>,
         context_picker_menu_handle: PopoverMenuHandle<ContextPicker>,
         suggest_context_kind: SuggestContextKind,
+        model_usage_context: ModelUsageContext,
         window: &mut Window,
         cx: &mut Context<Self>,
     ) -> Self {
@@ -81,6 +83,7 @@ impl ContextStrip {
             _subscriptions: subscriptions,
             focused_index: None,
             children_bounds: None,
+            model_usage_context,
         }
     }
 
@@ -98,11 +101,20 @@ impl ContextStrip {
                 .as_ref()
                 .and_then(|thread_store| thread_store.upgrade())
                 .and_then(|thread_store| thread_store.read(cx).prompt_store().as_ref());
+
+            let current_model = self.model_usage_context.language_model(cx);
+
             self.context_store
                 .read(cx)
                 .context()
                 .flat_map(|context| {
-                    AddedContext::new_pending(context.clone(), prompt_store, project, cx)
+                    AddedContext::new_pending(
+                        context.clone(),
+                        prompt_store,
+                        project,
+                        current_model.as_ref(),
+                        cx,
+                    )
                 })
                 .collect::<Vec<_>>()
         } else {
diff --git a/crates/agent/src/inline_prompt_editor.rs b/crates/agent/src/inline_prompt_editor.rs
index 624db3c19e..6aca18ceb8 100644
--- a/crates/agent/src/inline_prompt_editor.rs
+++ b/crates/agent/src/inline_prompt_editor.rs
@@ -912,6 +912,7 @@ impl PromptEditor<BufferCodegen> {
                 text_thread_store.clone(),
                 context_picker_menu_handle.clone(),
                 SuggestContextKind::Thread,
+                ModelUsageContext::InlineAssistant,
                 window,
                 cx,
             )
@@ -1083,6 +1084,7 @@ impl PromptEditor<TerminalCodegen> {
                 text_thread_store.clone(),
                 context_picker_menu_handle.clone(),
                 SuggestContextKind::Thread,
+                ModelUsageContext::InlineAssistant,
                 window,
                 cx,
             )
diff --git a/crates/agent/src/message_editor.rs b/crates/agent/src/message_editor.rs
index 8c620413a1..b9037e3e74 100644
--- a/crates/agent/src/message_editor.rs
+++ b/crates/agent/src/message_editor.rs
@@ -169,6 +169,7 @@ impl MessageEditor {
                 Some(text_thread_store.clone()),
                 context_picker_menu_handle.clone(),
                 SuggestContextKind::File,
+                ModelUsageContext::Thread(thread.clone()),
                 window,
                 cx,
             )
diff --git a/crates/agent/src/ui/context_pill.rs b/crates/agent/src/ui/context_pill.rs
index 605a142980..1abdd8fb8d 100644
--- a/crates/agent/src/ui/context_pill.rs
+++ b/crates/agent/src/ui/context_pill.rs
@@ -93,20 +93,9 @@ impl ContextPill {
             Self::Suggested {
                 icon_path: Some(icon_path),
                 ..
-            }
-            | Self::Added {
-                context:
-                    AddedContext {
-                        icon_path: Some(icon_path),
-                        ..
-                    },
-                ..
             } => Icon::from_path(icon_path),
-            Self::Suggested { kind, .. }
-            | Self::Added {
-                context: AddedContext { kind, .. },
-                ..
-            } => Icon::new(kind.icon()),
+            Self::Suggested { kind, .. } => Icon::new(kind.icon()),
+            Self::Added { context, .. } => context.icon(),
         }
     }
 }
@@ -133,6 +122,7 @@ impl RenderOnce for ContextPill {
                 on_click,
             } => {
                 let status_is_error = matches!(context.status, ContextStatus::Error { .. });
+                let status_is_warning = matches!(context.status, ContextStatus::Warning { .. });
 
                 base_pill
                     .pr(if on_remove.is_some() { px(2.) } else { px(4.) })
@@ -140,6 +130,9 @@ impl RenderOnce for ContextPill {
                         if status_is_error {
                             pill.bg(cx.theme().status().error_background)
                                 .border_color(cx.theme().status().error_border)
+                        } else if status_is_warning {
+                            pill.bg(cx.theme().status().warning_background)
+                                .border_color(cx.theme().status().warning_border)
                         } else if *focused {
                             pill.bg(color.element_background)
                                 .border_color(color.border_focused)
@@ -195,7 +188,8 @@ impl RenderOnce for ContextPill {
                                         |label, delta| label.opacity(delta),
                                     )
                                     .into_any_element(),
-                                ContextStatus::Error { message } => element
+                                ContextStatus::Warning { message }
+                                | ContextStatus::Error { message } => element
                                     .tooltip(ui::Tooltip::text(message.clone()))
                                     .into_any_element(),
                             }),
@@ -270,6 +264,7 @@ pub enum ContextStatus {
     Ready,
     Loading { message: SharedString },
     Error { message: SharedString },
+    Warning { message: SharedString },
 }
 
 #[derive(RegisterComponent)]
@@ -285,6 +280,19 @@ pub struct AddedContext {
 }
 
 impl AddedContext {
+    pub fn icon(&self) -> Icon {
+        match &self.status {
+            ContextStatus::Warning { .. } => Icon::new(IconName::Warning).color(Color::Warning),
+            ContextStatus::Error { .. } => Icon::new(IconName::XCircle).color(Color::Error),
+            _ => {
+                if let Some(icon_path) = &self.icon_path {
+                    Icon::from_path(icon_path)
+                } else {
+                    Icon::new(self.kind.icon())
+                }
+            }
+        }
+    }
     /// Creates an `AddedContext` by retrieving relevant details of `AgentContext`. This returns a
     /// `None` if `DirectoryContext` or `RulesContext` no longer exist.
     ///
@@ -293,6 +301,7 @@ impl AddedContext {
         handle: AgentContextHandle,
         prompt_store: Option<&Entity<PromptStore>>,
         project: &Project,
+        model: Option<&Arc<dyn language_model::LanguageModel>>,
         cx: &App,
     ) -> Option<AddedContext> {
         match handle {
@@ -304,11 +313,15 @@ impl AddedContext {
             AgentContextHandle::Thread(handle) => Some(Self::pending_thread(handle, cx)),
             AgentContextHandle::TextThread(handle) => Some(Self::pending_text_thread(handle, cx)),
             AgentContextHandle::Rules(handle) => Self::pending_rules(handle, prompt_store, cx),
-            AgentContextHandle::Image(handle) => Some(Self::image(handle, cx)),
+            AgentContextHandle::Image(handle) => Some(Self::image(handle, model, cx)),
         }
     }
 
-    pub fn new_attached(context: &AgentContext, cx: &App) -> AddedContext {
+    pub fn new_attached(
+        context: &AgentContext,
+        model: Option<&Arc<dyn language_model::LanguageModel>>,
+        cx: &App,
+    ) -> AddedContext {
         match context {
             AgentContext::File(context) => Self::attached_file(context, cx),
             AgentContext::Directory(context) => Self::attached_directory(context),
@@ -318,7 +331,7 @@ impl AddedContext {
             AgentContext::Thread(context) => Self::attached_thread(context),
             AgentContext::TextThread(context) => Self::attached_text_thread(context),
             AgentContext::Rules(context) => Self::attached_rules(context),
-            AgentContext::Image(context) => Self::image(context.clone(), cx),
+            AgentContext::Image(context) => Self::image(context.clone(), model, cx),
         }
     }
 
@@ -593,7 +606,11 @@ impl AddedContext {
         }
     }
 
-    fn image(context: ImageContext, cx: &App) -> AddedContext {
+    fn image(
+        context: ImageContext,
+        model: Option<&Arc<dyn language_model::LanguageModel>>,
+        cx: &App,
+    ) -> AddedContext {
         let (name, parent, icon_path) = if let Some(full_path) = context.full_path.as_ref() {
             let full_path_string: SharedString = full_path.to_string_lossy().into_owned().into();
             let (name, parent) =
@@ -604,21 +621,30 @@ impl AddedContext {
             ("Image".into(), None, None)
         };
 
+        let status = match context.status(model) {
+            ImageStatus::Loading => ContextStatus::Loading {
+                message: "Loading…".into(),
+            },
+            ImageStatus::Error => ContextStatus::Error {
+                message: "Failed to load Image".into(),
+            },
+            ImageStatus::Warning => ContextStatus::Warning {
+                message: format!(
+                    "{} doesn't support attaching Images as Context",
+                    model.map(|m| m.name().0).unwrap_or_else(|| "Model".into())
+                )
+                .into(),
+            },
+            ImageStatus::Ready => ContextStatus::Ready,
+        };
+
         AddedContext {
             kind: ContextKind::Image,
             name,
             parent,
             tooltip: None,
             icon_path,
-            status: match context.status() {
-                ImageStatus::Loading => ContextStatus::Loading {
-                    message: "Loading…".into(),
-                },
-                ImageStatus::Error => ContextStatus::Error {
-                    message: "Failed to load image".into(),
-                },
-                ImageStatus::Ready => ContextStatus::Ready,
-            },
+            status,
             render_hover: Some(Rc::new({
                 let image = context.original_image.clone();
                 move |_, cx| {
@@ -787,6 +813,7 @@ impl Component for AddedContext {
                     original_image: Arc::new(Image::empty()),
                     image_task: Task::ready(Some(LanguageModelImage::empty())).shared(),
                 },
+                None,
                 cx,
             ),
         );
@@ -806,6 +833,7 @@ impl Component for AddedContext {
                         })
                         .shared(),
                 },
+                None,
                 cx,
             ),
         );
@@ -820,6 +848,7 @@ impl Component for AddedContext {
                     original_image: Arc::new(Image::empty()),
                     image_task: Task::ready(None).shared(),
                 },
+                None,
                 cx,
             ),
         );
@@ -841,3 +870,60 @@ impl Component for AddedContext {
         )
     }
 }
+
+#[cfg(test)]
+mod tests {
+    use super::*;
+    use gpui::App;
+    use language_model::{LanguageModel, fake_provider::FakeLanguageModel};
+    use std::sync::Arc;
+
+    #[gpui::test]
+    fn test_image_context_warning_for_unsupported_model(cx: &mut App) {
+        let model: Arc<dyn LanguageModel> = Arc::new(FakeLanguageModel::default());
+        assert!(!model.supports_images());
+
+        let image_context = ImageContext {
+            context_id: ContextId::zero(),
+            project_path: None,
+            original_image: Arc::new(Image::empty()),
+            image_task: Task::ready(Some(LanguageModelImage::empty())).shared(),
+            full_path: None,
+        };
+
+        let added_context = AddedContext::image(image_context, Some(&model), cx);
+
+        assert!(matches!(
+            added_context.status,
+            ContextStatus::Warning { .. }
+        ));
+
+        assert!(matches!(added_context.kind, ContextKind::Image));
+        assert_eq!(added_context.name.as_ref(), "Image");
+        assert!(added_context.parent.is_none());
+        assert!(added_context.icon_path.is_none());
+    }
+
+    #[gpui::test]
+    fn test_image_context_ready_for_no_model(cx: &mut App) {
+        let image_context = ImageContext {
+            context_id: ContextId::zero(),
+            project_path: None,
+            original_image: Arc::new(Image::empty()),
+            image_task: Task::ready(Some(LanguageModelImage::empty())).shared(),
+            full_path: None,
+        };
+
+        let added_context = AddedContext::image(image_context, None, cx);
+
+        assert!(
+            matches!(added_context.status, ContextStatus::Ready),
+            "Expected ready status when no model provided"
+        );
+
+        assert!(matches!(added_context.kind, ContextKind::Image));
+        assert_eq!(added_context.name.as_ref(), "Image");
+        assert!(added_context.parent.is_none());
+        assert!(added_context.icon_path.is_none());
+    }
+}