diff --git a/extensions/bluebubbles/src/send.test.ts b/extensions/bluebubbles/src/send.test.ts
index e2f501f3fe4..6a3c6f01576 100644
--- a/extensions/bluebubbles/src/send.test.ts
+++ b/extensions/bluebubbles/src/send.test.ts
@@ -214,6 +214,90 @@ describe("send", () => {
       expect(result).toBe("iMessage;-;+15551234567");
     });
 
+    it("prefers iMessage over SMS when both chats exist for the same handle", async () => {
+      // Both chats exist; we should never silently downgrade to SMS.
+      const result = await resolveHandleTargetGuid([
+        {
+          guid: "SMS;-;+15551234567",
+          participants: [{ address: "+15551234567" }],
+        },
+        {
+          guid: "iMessage;-;+15551234567",
+          participants: [{ address: "+15551234567" }],
+        },
+      ]);
+
+      expect(result).toBe("iMessage;-;+15551234567");
+    });
+
+    it("prefers iMessage over SMS even when SMS appears first", async () => {
+      const result = await resolveHandleTargetGuid([
+        {
+          guid: "SMS;-;+15551234567",
+          participants: [{ address: "+15551234567" }],
+        },
+        {
+          guid: "iMessage;-;+15559999999",
+          participants: [{ address: "+15559999999" }],
+        },
+        {
+          guid: "iMessage;-;+15551234567",
+          participants: [{ address: "+15551234567" }],
+        },
+      ]);
+
+      expect(result).toBe("iMessage;-;+15551234567");
+    });
+
+    it("falls back to SMS when no iMessage chat exists for the handle", async () => {
+      // First page: SMS-only DM. Second page: empty (stops pagination).
+      mockFetch
+        .mockResolvedValueOnce({
+          ok: true,
+          json: () =>
+            Promise.resolve({
+              data: [
+                {
+                  guid: "SMS;-;+15551234567",
+                  participants: [{ address: "+15551234567" }],
+                },
+              ],
+            }),
+        })
+        .mockResolvedValueOnce({
+          ok: true,
+          json: () => Promise.resolve({ data: [] }),
+        });
+
+      const target: BlueBubblesSendTarget = {
+        kind: "handle",
+        address: "+15551234567",
+        service: "imessage",
+      };
+      const result = await resolveChatGuidForTarget({
+        baseUrl: "http://localhost:1234",
+        password: "test",
+        target,
+      });
+
+      expect(result).toBe("SMS;-;+15551234567");
+    });
+
+    it("prefers iMessage over SMS via participant match", async () => {
+      const result = await resolveHandleTargetGuid([
+        {
+          guid: "SMS;-;alt-handle",
+          participants: [{ address: "+15551234567" }],
+        },
+        {
+          guid: "iMessage;-;alt-handle",
+          participants: [{ address: "+15551234567" }],
+        },
+      ]);
+
+      expect(result).toBe("iMessage;-;alt-handle");
+    });
+
     it("returns null when handle only exists in group chat (not DM)", async () => {
       // This is the critical fix: if a phone number only exists as a participant in a group chat
       // (no direct DM chat), we should NOT send to that group. Return null instead.
diff --git a/extensions/bluebubbles/src/send.ts b/extensions/bluebubbles/src/send.ts
index 1e3b3c802d6..681b58b96e1 100644
--- a/extensions/bluebubbles/src/send.ts
+++ b/extensions/bluebubbles/src/send.ts
@@ -245,7 +245,13 @@ export async function resolveChatGuidForTarget(params: {
     params.target.kind === "chat_identifier" ? params.target.chatIdentifier : null;
 
   const limit = 500;
-  let participantMatch: string | null = null;
+  // When matching by handle, prefer iMessage over SMS. A user may have both
+  // an `iMessage;-;<handle>` and `SMS;-;<handle>` chat; we should never silently
+  // downgrade to SMS when an iMessage chat exists for the same handle.
+  let directHandleIMessageMatch: string | null = null;
+  let directHandleSmsMatch: string | null = null;
+  let participantIMessageMatch: string | null = null;
+  let participantSmsMatch: string | null = null;
   for (let offset = 0; offset < 5000; offset += limit) {
     const chats = await queryChats({
       baseUrl: params.baseUrl,
@@ -296,10 +302,21 @@ export async function resolveChatGuidForTarget(params: {
       if (normalizedHandle) {
         const guid = extractChatGuid(chat);
         const directHandle = guid ? extractHandleFromChatGuid(guid) : null;
-        if (directHandle && directHandle === normalizedHandle) {
-          return guid;
+        if (directHandle && directHandle === normalizedHandle && guid) {
+          // Prefer iMessage over SMS. If this chat is iMessage we can return
+          // immediately; if it is SMS we remember it as a fallback and keep
+          // scanning in case an iMessage chat for the same handle exists.
+          if (guid.startsWith("iMessage;-;")) {
+            return guid;
+          }
+          if (guid.startsWith("SMS;-;") && !directHandleSmsMatch) {
+            directHandleSmsMatch = guid;
+          } else if (!directHandleIMessageMatch && !directHandleSmsMatch) {
+            // Unknown service; treat as a last-resort direct match.
+            directHandleIMessageMatch = guid;
+          }
         }
-        if (!participantMatch && guid) {
+        if (guid && !participantIMessageMatch) {
           // Only consider DM chats (`;-;` separator) as participant matches.
           // Group chats (`;+;` separator) should never match when searching by handle/phone.
           // This prevents routing "send to +1234567890" to a group chat that contains that number.
@@ -309,14 +326,30 @@ export async function resolveChatGuidForTarget(params: {
               normalizeBlueBubblesHandle(entry),
             );
             if (participants.includes(normalizedHandle)) {
-              participantMatch = guid;
+              if (guid.startsWith("iMessage;-;")) {
+                participantIMessageMatch = guid;
+              } else if (guid.startsWith("SMS;-;") && !participantSmsMatch) {
+                participantSmsMatch = guid;
+              } else if (!participantSmsMatch) {
+                participantSmsMatch = guid;
+              }
             }
           }
         }
       }
     }
+    // If we already found an iMessage direct or participant match we can stop
+    // scanning further pages; any later SMS chat would still lose out.
+    if (directHandleIMessageMatch || participantIMessageMatch) {
+      break;
+    }
   }
-  return participantMatch;
+  return (
+    directHandleIMessageMatch ??
+    participantIMessageMatch ??
+    directHandleSmsMatch ??
+    participantSmsMatch
+  );
 }
 
 /**