diff --git a/packages/opencode/src/cli/cmd/tui/context/sync.tsx b/packages/opencode/src/cli/cmd/tui/context/sync.tsx
index 0edc911344c..db6112f3147 100644
--- a/packages/opencode/src/cli/cmd/tui/context/sync.tsx
+++ b/packages/opencode/src/cli/cmd/tui/context/sync.tsx
@@ -419,6 +419,58 @@ export const { use: useSync, provider: SyncProvider } = createSimpleContext({
           )
           fullSyncedSessions.add(sessionID)
         },
+        async loadConversationHistory(sessionID: string) {
+          const messages = store.message[sessionID]
+          if (!messages || messages.length === 0) return
+
+          const earliest = messages[0]
+          const result = await sdk.client.session.messages({
+            sessionID,
+            ts_before: earliest.time.created,
+            breakpoint: true,
+          })
+
+          if (!result.data || result.data.length === 0) {
+            return 0
+          }
+
+          setStore(
+            produce((draft) => {
+              const existing = draft.message[sessionID] ?? []
+              draft.message[sessionID] = [...result.data!.map((x) => x.info), ...existing]
+              for (const message of result.data!) {
+                draft.part[message.info.id] = message.parts
+              }
+            }),
+          )
+          return result.data.length
+        },
+        async loadFullSessionHistory(sessionID: string) {
+          const messages = store.message[sessionID]
+          if (!messages || messages.length === 0) return
+
+          const earliest = messages[0]
+          const result = await sdk.client.session.messages({
+            sessionID,
+            ts_before: earliest.time.created,
+            // Omit breakpoint - undefined is falsy and won't stop at compaction
+          })
+
+          if (!result.data || result.data.length === 0) {
+            return 0
+          }
+
+          setStore(
+            produce((draft) => {
+              const existing = draft.message[sessionID] ?? []
+              draft.message[sessionID] = [...result.data!.map((x) => x.info), ...existing]
+              for (const message of result.data!) {
+                draft.part[message.info.id] = message.parts
+              }
+            }),
+          )
+          return result.data.length
+        },
       },
       bootstrap,
     }
diff --git a/packages/opencode/src/cli/cmd/tui/routes/session/index.tsx b/packages/opencode/src/cli/cmd/tui/routes/session/index.tsx
index d91363954a1..cbe6bc2db5f 100644
--- a/packages/opencode/src/cli/cmd/tui/routes/session/index.tsx
+++ b/packages/opencode/src/cli/cmd/tui/routes/session/index.tsx
@@ -119,6 +119,22 @@ export function Session() {
       .toSorted((a, b) => (a.id < b.id ? -1 : a.id > b.id ? 1 : 0))
   })
   const messages = createMemo(() => sync.data.message[route.sessionID] ?? [])
+
+  const messagesDisplay = createMemo(() => {
+    const msgs = messages()
+    if (msgs.length >= 100) {
+      const synthetic = {
+        id: "__load_more__",
+        sessionID: route.sessionID,
+        role: "system" as const,
+        time: { created: 0, updated: 0, completed: null },
+        _synthetic: true,
+      } as any
+      return [synthetic, ...msgs]
+    }
+    return msgs
+  })
+
   const permissions = createMemo(() => {
     if (session()?.parentID) return []
     return children().flatMap((x) => sync.data.permission[x.id] ?? [])
@@ -926,9 +942,78 @@ export function Session() {
               flexGrow={1}
               scrollAcceleration={scrollAcceleration()}
             >
-              <For each={messages()}>
+              <For each={messagesDisplay()}>
                 {(message, index) => (
                   <Switch>
+                    <Match when={message.id === "__load_more__"}>
+                      {(function () {
+                        const [hoveredButton, setHoveredButton] = createSignal<"conversation" | "full" | null>(null)
+                        const [loading, setLoading] = createSignal(false)
+
+                        const handleLoadConversation = async () => {
+                          if (loading()) return
+                          setLoading(true)
+                          try {
+                            const count = await sync.session.loadConversationHistory(route.sessionID)
+                            if (count === 0) {
+                              toast.show({ message: "No more messages loaded", variant: "info" })
+                            } else {
+                              toast.show({ message: `History loaded (${count} messages)`, variant: "success" })
+                            }
+                          } finally {
+                            setLoading(false)
+                          }
+                        }
+
+                        const handleLoadFull = async () => {
+                          if (loading()) return
+                          setLoading(true)
+                          try {
+                            const count = await sync.session.loadFullSessionHistory(route.sessionID)
+                            if (count === 0) {
+                              toast.show({ message: "No more messages loaded", variant: "info" })
+                            } else {
+                              toast.show({ message: `History loaded (${count} messages)`, variant: "success" })
+                            }
+                          } finally {
+                            setLoading(false)
+                          }
+                        }
+
+                        return (
+                          <box
+                            paddingLeft={2}
+                            paddingRight={2}
+                            paddingTop={1}
+                            paddingBottom={1}
+                            marginBottom={1}
+                            flexDirection="row"
+                            backgroundColor={theme.backgroundPanel}
+                          >
+                            <text fg={theme.textMuted}>Load more messages: </text>
+                            <box
+                              onMouseOver={() => setHoveredButton("conversation")}
+                              onMouseOut={() => setHoveredButton(null)}
+                              onMouseUp={handleLoadConversation}
+                            >
+                              <text fg={hoveredButton() === "conversation" ? theme.accent : theme.text}>
+                                load conversation history
+                              </text>
+                            </box>
+                            <text fg={theme.textMuted}> or </text>
+                            <box
+                              onMouseOver={() => setHoveredButton("full")}
+                              onMouseOut={() => setHoveredButton(null)}
+                              onMouseUp={handleLoadFull}
+                            >
+                              <text fg={hoveredButton() === "full" ? theme.accent : theme.text}>
+                                load full session history
+                              </text>
+                            </box>
+                          </box>
+                        )
+                      })()}
+                    </Match>
                     <Match when={message.id === revert()?.messageID}>
                       {(function () {
                         const command = useCommandDialog()
diff --git a/packages/opencode/src/server/server.ts b/packages/opencode/src/server/server.ts
index 7015c818822..38608aad207 100644
--- a/packages/opencode/src/server/server.ts
+++ b/packages/opencode/src/server/server.ts
@@ -1251,6 +1251,8 @@ export namespace Server {
             "query",
             z.object({
               limit: z.coerce.number().optional(),
+              ts_before: z.coerce.number().optional(),
+              breakpoint: z.coerce.boolean().optional(),
             }),
           ),
           async (c) => {
@@ -1258,6 +1260,8 @@ export namespace Server {
             const messages = await Session.messages({
               sessionID: c.req.valid("param").sessionID,
               limit: query.limit,
+              ts_before: query.ts_before,
+              breakpoint: query.breakpoint,
             })
             return c.json(messages)
           },
diff --git a/packages/opencode/src/session/index.ts b/packages/opencode/src/session/index.ts
index 3fcdab5238c..0318d5763c3 100644
--- a/packages/opencode/src/session/index.ts
+++ b/packages/opencode/src/session/index.ts
@@ -293,12 +293,26 @@ export namespace Session {
     z.object({
       sessionID: Identifier.schema("session"),
       limit: z.number().optional(),
+      ts_before: z.number().optional(),
+      breakpoint: z.boolean().optional(),
     }),
     async (input) => {
       const result = [] as MessageV2.WithParts[]
+
       for await (const msg of MessageV2.stream(input.sessionID)) {
+        if (input.ts_before && msg.info.time.created >= input.ts_before) {
+          continue
+        }
+
         if (input.limit && result.length >= input.limit) break
         result.push(msg)
+
+        if (input.ts_before && input.breakpoint) {
+          const hasCompaction = msg.parts.some((p) => p.type === "compaction")
+          if (hasCompaction) {
+            break
+          }
+        }
       }
       result.reverse()
       return result
diff --git a/packages/sdk/js/src/v2/gen/sdk.gen.ts b/packages/sdk/js/src/v2/gen/sdk.gen.ts
index 697dac7eefe..0297c1df57c 100644
--- a/packages/sdk/js/src/v2/gen/sdk.gen.ts
+++ b/packages/sdk/js/src/v2/gen/sdk.gen.ts
@@ -1279,6 +1279,8 @@ export class Session extends HeyApiClient {
       sessionID: string
       directory?: string
       limit?: number
+      ts_before?: number
+      breakpoint?: boolean
     },
     options?: Options<never, ThrowOnError>,
   ) {
@@ -1290,6 +1292,8 @@ export class Session extends HeyApiClient {
             { in: "path", key: "sessionID" },
             { in: "query", key: "directory" },
             { in: "query", key: "limit" },
+            { in: "query", key: "ts_before" },
+            { in: "query", key: "breakpoint" },
           ],
         },
       ],
diff --git a/packages/sdk/js/src/v2/gen/types.gen.ts b/packages/sdk/js/src/v2/gen/types.gen.ts
index 9c4f0e50d12..19c953e2932 100644
--- a/packages/sdk/js/src/v2/gen/types.gen.ts
+++ b/packages/sdk/js/src/v2/gen/types.gen.ts
@@ -3122,6 +3122,8 @@ export type SessionMessagesData = {
   query?: {
     directory?: string
     limit?: number
+    ts_before?: number
+    breakpoint?: boolean
   }
   url: "/session/{sessionID}/message"
 }
diff --git a/packages/sdk/openapi.json b/packages/sdk/openapi.json
index 20b1029fc96..f9e14033dd2 100644
--- a/packages/sdk/openapi.json
+++ b/packages/sdk/openapi.json
@@ -2008,6 +2008,20 @@
             "schema": {
               "type": "number"
             }
+          },
+          {
+            "in": "query",
+            "name": "ts_before",
+            "schema": {
+              "type": "number"
+            }
+          },
+          {
+            "in": "query",
+            "name": "breakpoint",
+            "schema": {
+              "type": "boolean"
+            }
           }
         ],
         "summary": "Get session messages",