diff --git a/vllm/entrypoints/openai/make_prompt.py b/vllm/entrypoints/openai/make_prompt.py
new file mode 100644
index 0000000000000..185131a30883b
--- /dev/null
+++ b/vllm/entrypoints/openai/make_prompt.py
@@ -0,0 +1,56 @@
+import re
+from io import BytesIO
+from PIL import Image
+
+from transformers import PreTrainedTokenizer
+from base64 import b64decode
+
+from .protocol import ChatCompletionRequest
+from .pdf_reader import read_doc
+
+
+DEFAULT_SYSTEM_PROMPT = """You are a helpful, respectful and honest assistant. Always answer as helpfully as possible, while being safe. Your answers should not include any harmful, unethical, racist, sexist, toxic, dangerous, or illegal content. Please ensure that your responses are socially unbiased and positive in nature.
+
+If a question does not make any sense, or is not factually coherent, explain why instead of answering something not correct. If you don't know the answer to a question, please don't share false information."""
+
+
+def make_prompt(request: ChatCompletionRequest,
+                tokenizer: PreTrainedTokenizer):
+
+    for msg in request.messages:
+        if msg['role'] == 'system' and msg['content'] == "":
+            msg['content'] = DEFAULT_SYSTEM_PROMPT
+
+        def replace_file(match):
+            display_text = match.group(1)
+            mime_type = match.group(2)
+            base64_string = match.group(3)
+
+            # Convert base64 to bytesIO
+            file = BytesIO(b64decode(base64_string, validate=True))
+            if mime_type.startswith('image/'):
+                image = Image.open(file)
+                # TODO: encode image to tokens
+                return display_text
+            elif mime_type == "application/pdf":
+                texts = read_doc(file, mime_type)
+                result = (
+                    f"[Begin document]" +
+                    "\n".join([f"(Page {t.page}) {t.text}" for t in texts]) +
+                    f"[End document]"
+                )
+                return result
+            else:
+                raise ValueError(f"Unsupported mime type: {mime_type}")
+
+        msg['content'] = re.sub(
+            r'!\[([^\]]*)]\(data:([^;]*);base64,([-A-Za-z0-9+/]*={0,3})\)',
+            replace_file, msg['content']
+        )
+
+    prompt = tokenizer.apply_chat_template(
+        conversation=request.messages,
+        tokenize=False,
+        add_generation_prompt=request.add_generation_prompt)
+
+    return prompt
diff --git a/vllm/entrypoints/openai/pdf_reader.py b/vllm/entrypoints/openai/pdf_reader.py
new file mode 100644
index 0000000000000..76a5ac44c3bcb
--- /dev/null
+++ b/vllm/entrypoints/openai/pdf_reader.py
@@ -0,0 +1,149 @@
+import io
+from math import ceil
+from pathlib import Path
+from typing import List, BinaryIO
+
+import tiktoken
+from dataclasses import dataclass
+from html2text import html2text
+import fitz
+import pypdf
+
+
+@dataclass
+class Text:
+    text: str
+    page: str
+
+
+def parse_pdf_fitz(file: BinaryIO, chunk_chars: int, overlap: int) -> List[Text]:
+    file = fitz.open(stream=file, filetype="pdf")
+    split = ""
+    pages: List[str] = []
+    texts: List[Text] = []
+    for i in range(file.page_count):
+        page = file.load_page(i)
+        split += page.get_text("text", sort=True)
+        pages.append(str(i + 1))
+        # split could be so long it needs to be split
+        # into multiple chunks. Or it could be so short
+        # that it needs to be combined with the next chunk.
+        while len(split) > chunk_chars:
+            # pretty formatting of pages (e.g. 1-3, 4, 5-7)
+            pg = "-".join([pages[0], pages[-1]])
+            texts.append(Text(text=split[:chunk_chars], page=pg))
+            split = split[chunk_chars - overlap:]
+            pages = [str(i + 1)]
+    if len(split) > overlap or len(texts) == 0:
+        pg = "-".join([pages[0], pages[-1]])
+        texts.append(Text(text=split[:chunk_chars], page=pg))
+    file.close()
+    return texts
+
+
+def parse_pdf(file: BinaryIO, chunk_chars: int, overlap: int) -> List[Text]:
+    pdfReader = pypdf.PdfReader(file)
+    split = ""
+    pages: List[str] = []
+    texts: List[Text] = []
+    for i, page in enumerate(pdfReader.pages):
+        split += page.extract_text()
+        pages.append(str(i + 1))
+        # split could be so long it needs to be split
+        # into multiple chunks. Or it could be so short
+        # that it needs to be combined with the next chunk.
+        while len(split) > chunk_chars:
+            # pretty formatting of pages (e.g. 1-3, 4, 5-7)
+            pg = "-".join([pages[0], pages[-1]])
+            texts.append(Text(text=split[:chunk_chars], page=pg))
+            split = split[chunk_chars - overlap:]
+            pages = [str(i + 1)]
+    if len(split) > overlap or len(texts) == 0:
+        pg = "-".join([pages[0], pages[-1]])
+        texts.append(
+            Text(text=split[:chunk_chars], page=pg)
+        )
+    return texts
+
+
+def parse_txt(
+    file: BinaryIO, chunk_chars: int, overlap: int, html: bool = False
+) -> List[Text]:
+    """Parse a document into chunks, based on tiktoken encoding.
+
+    NOTE: We get some byte continuation errors.
+    Currnetly ignored, but should explore more to make sure we
+    don't miss anything.
+    """
+    try:
+        f = io.TextIOWrapper(file)
+        text = f.read()
+    except UnicodeDecodeError:
+        f = io.TextIOWrapper(file, encoding="utf-8", errors="ignore")
+        text = f.read()
+    if html:
+        text = html2text(text)
+    texts: list[Text] = []
+    # we tokenize using tiktoken so cuts are in reasonable places
+    # See https://github.com/openai/tiktoken
+    enc = tiktoken.get_encoding("cl100k_base")
+    encoded = enc.encode_ordinary(text)
+    split = []
+    # convert from characters to chunks
+    char_count = len(text)  # e.g., 25,000
+    token_count = len(encoded)  # e.g., 4,500
+    chars_per_token = char_count / token_count  # e.g., 5.5
+    chunk_tokens = chunk_chars / chars_per_token  # e.g., 3000 / 5.5 = 545
+    overlap_tokens = overlap / chars_per_token  # e.g., 100 / 5.5 = 18
+    chunk_count = ceil(token_count / chunk_tokens)  # e.g., 4500 / 545 = 9
+    for i in range(chunk_count):
+        split = encoded[
+            max(int(i * chunk_tokens - overlap_tokens), 0) : int(
+                (i + 1) * chunk_tokens + overlap_tokens
+            )
+        ]
+        texts.append(Text(text=enc.decode(split), page=f"{i + 1}"))
+    return texts
+
+
+def parse_code_txt(file: BinaryIO, chunk_chars: int, overlap: int) -> List[Text]:
+    """Parse a document into chunks, based on line numbers (for code)."""
+
+    split = ""
+    texts: List[Text] = []
+    last_line = 0
+
+    f = io.TextIOWrapper(file)
+    for i, line in enumerate(f):
+        split += line
+        while len(split) > chunk_chars:
+            texts.append(
+                Text(text=split[:chunk_chars], page=f"{last_line}-{i}"))
+            split = split[chunk_chars - overlap:]
+            last_line = i
+    if len(split) > overlap or len(texts) == 0:
+        texts.append(Text(text=split[:chunk_chars], page=f"{last_line}-{i}"))
+    return texts
+
+
+def read_doc(
+    file: BinaryIO,
+    mime_type: str,
+    chunk_chars: int = 3000,
+    overlap: int = 100,
+    force_pypdf: bool = False,
+) -> List[Text]:
+    """Parse a document into chunks."""
+    if mime_type == "application/pdf":
+        if force_pypdf:
+            return parse_pdf(file, chunk_chars, overlap)
+        try:
+            return parse_pdf_fitz(file, chunk_chars, overlap)
+        except ImportError:
+            return parse_pdf(file, chunk_chars, overlap)
+    elif mime_type == "text/plain":
+        return parse_txt(file, chunk_chars, overlap)
+    elif mime_type == "text/html":
+        return parse_txt(file, chunk_chars, overlap, html=True)
+    else:
+        return parse_code_txt(file, chunk_chars, overlap)
diff --git a/vllm/entrypoints/openai/serving_chat.py b/vllm/entrypoints/openai/serving_chat.py
index a9e4c355560b8..584844e1ccbdb 100644
--- a/vllm/entrypoints/openai/serving_chat.py
+++ b/vllm/entrypoints/openai/serving_chat.py
@@ -1,7 +1,11 @@
+import re
 import time
 import codecs
+from io import BytesIO
+
 from fastapi import Request
 from typing import AsyncGenerator, AsyncIterator, Union
+
 from vllm.logger import init_logger
 from vllm.utils import random_uuid
 from vllm.engine.async_llm_engine import AsyncLLMEngine
@@ -13,6 +17,8 @@
 from vllm.outputs import RequestOutput
 from vllm.entrypoints.openai.serving_engine import OpenAIServing
 
+from .make_prompt import make_prompt
+
 logger = init_logger(__name__)
 
 
@@ -50,10 +56,7 @@ async def create_chat_completion(
                 "logit_bias is not currently supported")
 
         try:
-            prompt = self.tokenizer.apply_chat_template(
-                conversation=request.messages,
-                tokenize=False,
-                add_generation_prompt=request.add_generation_prompt)
+            prompt = make_prompt(request, self.tokenizer)
         except Exception as e:
             logger.error(
                 f"Error in applying chat template from request: {str(e)}")
diff --git a/vllm/entrypoints/openai/serving_engine.py b/vllm/entrypoints/openai/serving_engine.py
index 390f9aeb89217..6e670ce63b3e5 100644
--- a/vllm/entrypoints/openai/serving_engine.py
+++ b/vllm/entrypoints/openai/serving_engine.py
@@ -116,7 +116,7 @@ def _validate_prompt_and_tokenize(
                 "Only one of prompt or prompt_ids should be provided.")
 
         input_ids = prompt_ids if prompt_ids is not None else self.tokenizer(
-            prompt).input_ids
+            prompt, add_special_tokens=False).input_ids
         token_num = len(input_ids)
 
         if request.max_tokens is None: