diff --git a/common/prompt.ts b/common/prompt.ts
index 63127473b..02c2b44dd 100644
--- a/common/prompt.ts
+++ b/common/prompt.ts
@@ -422,10 +422,6 @@ export async function buildPromptParts(
 
   const post = createPostPrompt(opts)
 
-  if (opts.continue) {
-    post.unshift(`${char.name}: ${opts.continue}`)
-  }
-
   const linesForMemory = [...lines].reverse()
   const books: AppSchema.MemoryBook[] = []
   if (replyAs.characterBook) books.push(replyAs.characterBook)
diff --git a/common/template-parser.ts b/common/template-parser.ts
index 07f03f914..f931e4746 100644
--- a/common/template-parser.ts
+++ b/common/template-parser.ts
@@ -138,7 +138,30 @@ export async function parseTemplate(
     parts.ujb = render(parts.ujb, opts)
   }
 
-  const ast = parser.parse(template, {}) as PNode[]
+  let ast = parser.parse(template, {}) as PNode[]
+
+  /**
+   * Continuing the previous message:
+   * In this case our goal is to end the prompt as close to the
+   * last message as possible.
+   */
+  if (opts.continue) {
+    const historyIndex = ast.findIndex(
+      (node) =>
+        typeof node !== 'string' &&
+        ((node.kind === 'placeholder' && node.value === 'history') ||
+          (node.kind === 'each' && node.value === 'history'))
+    )
+    if (historyIndex !== -1) {
+      const node = ast[historyIndex] as PlaceHolder | IteratorNode
+      // replace iterator with normalized history
+      if (node.kind === 'each' && node.value === 'history') {
+        ast[historyIndex] = { kind: 'placeholder', value: 'history' } as PlaceHolder
+      }
+      ast = ast.slice(0, historyIndex + 1)
+    }
+  }
+
   readInserts(opts, ast)
   let output = render(template, opts, ast)
   let unusedTokens = 0
diff --git a/common/util.ts b/common/util.ts
index 521b44144..24ecc992e 100644
--- a/common/util.ts
+++ b/common/util.ts
@@ -175,6 +175,15 @@ export function trimSentence(text: string) {
   return index === -1 ? text.trimEnd() : text.slice(0, index + 1).trimEnd()
 }
 
+export function concatenateSentence(text: string, next: string) {
+  if (!text || !next) return `${text}${next}`
+  if (next.startsWith('\n')) {
+    return `${text.trimEnd()}\n${next.trimStart()}`
+  }
+
+  return `${text.trimEnd()}${next}`
+}
+
 export function slugify(str: string) {
   return str
     .toLowerCase()
diff --git a/srv/api/chat/message.ts b/srv/api/chat/message.ts
index 120bdac4d..d812f1590 100644
--- a/srv/api/chat/message.ts
+++ b/srv/api/chat/message.ts
@@ -9,6 +9,7 @@ import { v4 } from 'uuid'
 import { Response } from 'express'
 import { publishMany } from '../ws/handle'
 import { getScenarioEventType } from '/common/scenario'
+import { concatenateSentence } from '/common/util'
 
 type GenRequest = UnwrapBody<typeof genValidator>
 
@@ -331,7 +332,9 @@ export const generateMessageV2 = handle(async (req, res) => {
     return
   }
 
-  const responseText = body.kind === 'continue' ? `${body.continuing.msg} ${generated}` : generated
+  const responseText =
+    body.kind === 'continue' ? concatenateSentence(body.continuing.msg, generated) : generated
+
   const actions: AppSchema.ChatAction[] = []
 
   switch (body.kind) {
@@ -568,7 +571,8 @@ async function handleGuestGenerate(body: GenRequest, req: AppRequest, res: Respo
 
   if (error) return
 
-  const responseText = body.kind === 'continue' ? `${body.continuing.msg} ${generated}` : generated
+  const responseText =
+    body.kind === 'continue' ? concatenateSentence(body.continuing.msg, generated) : generated
 
   const characterId = body.kind === 'self' ? undefined : body.replyAs?._id || body.char?._id
   const senderId = body.kind === 'self' ? 'anon' : undefined
diff --git a/tests/__snapshots__/prompt.spec.js.snap b/tests/__snapshots__/prompt.spec.js.snap
index f05e4c982..8ccc1ccb6 100644
--- a/tests/__snapshots__/prompt.spec.js.snap
+++ b/tests/__snapshots__/prompt.spec.js.snap
@@ -32,7 +32,6 @@ How MainChar speaks: SAMPLECHAT MainChar
 
 <START>
 MainChar: FIRST
-MainChar: ORIGINAL
 MainChar:"
 `;
 
@@ -99,7 +98,6 @@ Scenario: MAIN MainChar
 This is how OtherBot should talk: SAMPLECHAT OtherBot
 MainChar: FIRST
 ChatOwner: SECOND
-MainChar: ORIGINAL
 OtherBot:"
 `;
 
@@ -165,7 +163,6 @@ SAMPLECHAT OtherBot
 System: New conversation started. Previous conversations are examples only.
 MainChar: FIRST
 ChatOwner: SECOND
-MainChar: ORIGINAL
 OtherBot:"
 `;