diff --git a/crates/client/src/search/index.rs b/crates/client/src/search/index.rs
index 8638ec20..c198bff4 100644
--- a/crates/client/src/search/index.rs
+++ b/crates/client/src/search/index.rs
@@ -16,6 +16,59 @@ use std::sync::Arc;
 
 use willow_identity::EndpointId;
 
+use crate::state::DisplayMessage;
+
+/// File extensions that classify a body / attachment as an image for
+/// the `has:image` operator. Mirrors the web UI's `IMAGE_EXTENSIONS`
+/// list in `crates/web/src/components/message.rs` — keep in sync if
+/// either one grows.
+const IMAGE_EXTENSIONS: &[&str] = &[
+    ".png", ".jpg", ".jpeg", ".gif", ".webp", ".svg", ".bmp", ".ico",
+];
+
+/// Strip an inline-file body of the form `[file:NAME:BASE64]` and
+/// return `NAME`. Returns `None` for plain bodies.
+///
+/// The web UI sends inline file attachments via this body shape (see
+/// `crates/client/src/actions.rs::share_file_inline`), so the indexer
+/// classifies attachments by sniffing the body without needing a
+/// separate attachments field on `DisplayMessage`.
+fn inline_file_name(body: &str) -> Option<&str> {
+    let inner = body.strip_prefix("[file:")?.strip_suffix(']')?;
+    let colon = inner.find(':')?;
+    Some(&inner[..colon])
+}
+
+/// True if `name` ends with an image-file extension (case-insensitive).
+fn is_image_name(name: &str) -> bool {
+    let lower = name.to_lowercase();
+    IMAGE_EXTENSIONS.iter().any(|ext| lower.ends_with(ext))
+}
+
+/// True if `body` contains a URL whose path ends in an image
+/// extension. Cheap scan — proper URL parsing happens in the message
+/// row renderer; this mirror only needs to be precise enough for the
+/// `has:image` operator.
+fn body_has_image_url(body: &str) -> bool {
+    for prefix in ["http://", "https://"] {
+        let mut rest = body;
+        while let Some(idx) = rest.find(prefix) {
+            let url_start = idx;
+            let after = &rest[url_start..];
+            let url_end = after
+                .find(|c: char| c.is_whitespace() || c == '>' || c == ')' || c == ']')
+                .unwrap_or(after.len());
+            let url = &after[..url_end];
+            let path = url.split('?').next().unwrap_or(url);
+            if is_image_name(path) {
+                return true;
+            }
+            rest = &after[url_end..];
+        }
+    }
+    false
+}
+
 /// One message ready to be indexed.
 ///
 /// All the metadata the executor needs to apply scope + operator
@@ -51,6 +104,58 @@ pub struct IndexableMessage {
     pub has_link: bool,
 }
 
+impl IndexableMessage {
+    /// Build an [`IndexableMessage`] from a [`DisplayMessage`], with
+    /// the operator-flag fields (`has_image`, `has_file`, `has_link`)
+    /// derived from the body so the search executor's `has:image` /
+    /// `has:file` / `has:link` filters actually match.
+    ///
+    /// Per `docs/specs/2026-04-19-ui-design/local-search.md` §Operators:
+    /// the index is the source of truth for `has:` filtering.
+    /// Classification rules:
+    ///
+    /// - Inline `[file:NAME:b64]` bodies (sent by
+    ///   `share_file_inline`) → `has_image` if `NAME` has an image
+    ///   extension, else `has_file`.
+    /// - Bare URLs whose path ends in an image extension →
+    ///   `has_image` (`https://example.com/cat.jpg`).
+    /// - Any `http://` or `https://` substring → `has_link`.
+    ///
+    /// `letter_id` is plumbed through verbatim — the caller resolves
+    /// it from the active letter context (or passes `None` for
+    /// grove-channel messages). See issue #355 for the missing
+    /// plumbing context.
+    pub fn from_display_message(
+        m: &DisplayMessage,
+        channel_name: &str,
+        grove_id: Option<String>,
+        letter_id: Option<String>,
+    ) -> Self {
+        let inline_name = inline_file_name(&m.body);
+        let has_inline_image = inline_name.is_some_and(is_image_name);
+        let has_inline_file = inline_name.is_some() && !has_inline_image;
+        let has_image = has_inline_image || body_has_image_url(&m.body);
+        let has_file = has_inline_file;
+        let has_link = m.body.contains("http://") || m.body.contains("https://");
+
+        Self {
+            message_id: m.id.clone(),
+            channel_id: m.channel_id.clone(),
+            channel_name: channel_name.to_string(),
+            grove_id,
+            letter_id,
+            author_peer_id: m.author_peer_id,
+            author_handle: m.author_display_name.to_lowercase(),
+            author_display_name: m.author_display_name.clone(),
+            timestamp_ms: m.timestamp_ms,
+            body: m.body.clone(),
+            has_image,
+            has_file,
+            has_link,
+        }
+    }
+}
+
 /// One row stored in the inverted index. Cheaply cloned into
 /// `SearchResult`s at execute time.
 #[derive(Debug, Clone, PartialEq, Eq)]
diff --git a/crates/client/src/search/tests.rs b/crates/client/src/search/tests.rs
index f24951dd..f1fa7432 100644
--- a/crates/client/src/search/tests.rs
+++ b/crates/client/src/search/tests.rs
@@ -940,3 +940,102 @@ mod query_tests {
         assert_eq!(q.raw, "Hello");
     }
 }
+
+mod from_display_message_tests {
+    //! `IndexableMessage::from_display_message` derives the operator
+    //! flags (`has_image`, `has_file`, `has_link`) from a
+    //! [`DisplayMessage`]. Per `docs/specs/2026-04-19-ui-design/local-search.md`
+    //! §Operators, the index must populate these so `has:image` /
+    //! `has:file` / `has:link` queries actually match — see issue
+    //! #355.
+    use super::super::index::IndexableMessage;
+    use crate::state::{DisplayMessage, QueueNote};
+    use std::collections::HashMap;
+    use willow_identity::Identity;
+
+    fn dm(id: &str, body: &str) -> DisplayMessage {
+        DisplayMessage {
+            id: id.into(),
+            channel_id: "c1".into(),
+            author_peer_id: Identity::generate().endpoint_id(),
+            author_display_name: "Mira".into(),
+            body: body.into(),
+            is_local: false,
+            timestamp_ms: 100,
+            reactions: HashMap::new(),
+            edited: false,
+            deleted: false,
+            reply_to: None,
+            reply_preview: None,
+            mentions: Vec::new(),
+            pinned: false,
+            whisper: false,
+            queue_note: QueueNote::None,
+        }
+    }
+
+    #[test]
+    fn inline_image_attachment_sets_has_image() {
+        // `[file:NAME:b64]` where NAME has an image extension renders
+        // inline as an image embed in the web UI; the index must
+        // mirror that classification so `has:image` matches.
+        let body = format!(
+            "[file:photo.png:{}]",
+            crate::base64::encode(b"\x89PNG\r\n\x1a\n")
+        );
+        let m = dm("m1", &body);
+        let ix = IndexableMessage::from_display_message(&m, "general", None, None);
+        assert!(ix.has_image, "image attachment must set has_image");
+        assert!(!ix.has_file, "image attachment must not set has_file");
+    }
+
+    #[test]
+    fn inline_non_image_attachment_sets_has_file() {
+        let body = format!("[file:notes.txt:{}]", crate::base64::encode(b"hello"));
+        let m = dm("m2", &body);
+        let ix = IndexableMessage::from_display_message(&m, "general", None, None);
+        assert!(ix.has_file, "non-image attachment must set has_file");
+        assert!(!ix.has_image, "non-image attachment must not set has_image");
+    }
+
+    #[test]
+    fn image_url_in_body_sets_has_image() {
+        // Bare URL pointing at an image extension also lights up
+        // `has:image` — mirrors the UI's `is_image_url` rule.
+        let m = dm("m3", "look at https://example.com/cat.jpg");
+        let ix = IndexableMessage::from_display_message(&m, "general", None, None);
+        assert!(ix.has_image, "image URL must set has_image");
+        assert!(ix.has_link, "URL must set has_link");
+    }
+
+    #[test]
+    fn plain_url_sets_has_link_only() {
+        let m = dm("m4", "see https://willow.im/docs");
+        let ix = IndexableMessage::from_display_message(&m, "general", None, None);
+        assert!(ix.has_link);
+        assert!(!ix.has_image);
+        assert!(!ix.has_file);
+    }
+
+    #[test]
+    fn plain_text_sets_no_flags() {
+        let m = dm("m5", "hello world");
+        let ix = IndexableMessage::from_display_message(&m, "general", None, None);
+        assert!(!ix.has_image);
+        assert!(!ix.has_file);
+        assert!(!ix.has_link);
+    }
+
+    #[test]
+    fn grove_and_letter_id_passed_through() {
+        let m = dm("m6", "hi");
+        let ix = IndexableMessage::from_display_message(
+            &m,
+            "general",
+            Some("g0".into()),
+            Some("L1".into()),
+        );
+        assert_eq!(ix.grove_id.as_deref(), Some("g0"));
+        assert_eq!(ix.letter_id.as_deref(), Some("L1"));
+    }
+}
diff --git a/crates/web/src/app.rs b/crates/web/src/app.rs
index 06c15bb7..e8accfa2 100644
--- a/crates/web/src/app.rs
+++ b/crates/web/src/app.rs
@@ -379,33 +379,26 @@ pub fn App() -> impl IntoView {
             let grove_id = active_server_sig.get();
             let local_peer = peer_id_sig.get();
 
+            // `IndexableMessage::from_display_message` derives the
+            // `has_image` / `has_file` / `has_link` operator flags
+            // from the body so `has:image` / `has:file` / `has:link`
+            // queries actually match. `letter_id` stays `None` here —
+            // the active-letter signal isn't yet wired into this
+            // effect; tracked as a follow-up to issue #355.
+            let grove = if grove_id.is_empty() {
+                None
+            } else {
+                Some(grove_id.clone())
+            };
             let indexable: Vec<willow_client::IndexableMessage> = msgs
                 .into_iter()
                 .map(|m| {
-                    let author_peer_id = m.author_peer_id;
-                    // Lightweight link detection — `has:link` operator
-                    // key. Proper URL parsing lives in message-row
-                    // rendering; this is the cheap version.
-                    let has_link = m.body.contains("http://") || m.body.contains("https://");
-                    willow_client::IndexableMessage {
-                        message_id: m.id,
-                        channel_id: m.channel_id.clone(),
-                        channel_name: current_ch.clone(),
-                        grove_id: if grove_id.is_empty() {
-                            None
-                        } else {
-                            Some(grove_id.clone())
-                        },
-                        letter_id: None,
-                        author_peer_id,
-                        author_handle: m.author_display_name.to_lowercase(),
-                        author_display_name: m.author_display_name,
-                        timestamp_ms: m.timestamp_ms,
-                        body: m.body,
-                        has_image: false,
-                        has_file: false,
-                        has_link,
-                    }
+                    willow_client::IndexableMessage::from_display_message(
+                        &m,
+                        &current_ch,
+                        grove.clone(),
+                        None,
+                    )
                 })
                 .collect();
             // Ignore local peer binding to avoid unused_variables clippy