diff --git a/docs/commands/misc/ai.md b/docs/commands/misc/ai.md
new file mode 100644
index 000000000..1678c6cd8
--- /dev/null
+++ b/docs/commands/misc/ai.md
@@ -0,0 +1,50 @@
+## Command ai ##
+```
+usage: ai [-h] [-M MODEL] [-t TEMPERATURE] [-m MAX_TOKENS] [-v] [-c COMMAND] <QUESTION>
+```
+
+| Positional Argument | Info |
+|---------------------|------|
+| QUESTION | The question you want to ask GPT-3 about the current context or command output. |
+
+| Optional Argument | Info |
+|-------------------|------|
+| -h | show a help message |
+| -M MODEL | specify which language model GPT-3 should use (default: text-davinci-003) |
+| -t TEMPERATURE | set the temperature for the response, between 0.0 and 2.0, with higher temperatures provoking more 'adventurous' responses |
+| -m MAX\_TOKENS | set the size of the response in token count, but note that there is a limit of 4096 tokens for the prompt and response combined, and a token is about 3 characters on average |
+| -v | verbose mode -- show the prompt as well as the response |
+| -c COMMAND | instead of asking about the context, run a gdb command and ask about its output |
+
+
+If you have the [`openai`](https://github.com/openai/openai-python) Python
+module installed, and the `OPENAI_API_KEY` environment variable set to a valid
+OpenAI API key, then the `ai` command can be used to query the GPT-3 large
+language model for insights into the current debugging context. The register
+state, the stack, and the nearby assembly instructions will be made visible
+to the model, along with the nearby source code, if the binary was compiled
+with debugging information.
+
+
+### Examples ###
+
+```
+pwndbg> ai what was the name of the function most recently called?
+ strcmp
+
+pwndbg> ai how do you know this?
+ The assembly code shows that the function call 0x7ffff7fea240 <strcmp> was made just before the current instruction at 0x7ffff7fce2a7 <check_match+103>.
+
+pwndbg> ai what will the next two instructions do the the eax and ecx registers?
+
+ The next two instructions will move the values stored in the esi and edi registers into the eax and ecx registers, respectively.
+
+pwndbg> ai say that again but as a limerick
+
+The eax and ecx registers will fill
+With the values stored in esi and edi still
+The instructions will move
+Their values to improve
+And the registers will have a new thrill
+
+```
diff --git a/mkdocs.yml b/mkdocs.yml
index 9f48547ff..447a1c7ea 100644
--- a/mkdocs.yml
+++ b/mkdocs.yml
@@ -149,6 +149,7 @@ nav:
       - up: commands/misc/up.md
       - down: commands/misc/down.md
       - r2: commands/misc/r2.md
+      - ai: commands/misc/ai.md
 
     - Arm:
       - cpsr: commands/arm/cpsr.md
diff --git a/pwndbg/commands/__init__.py b/pwndbg/commands/__init__.py
index d62d16843..029f16f31 100644
--- a/pwndbg/commands/__init__.py
+++ b/pwndbg/commands/__init__.py
@@ -597,6 +597,7 @@ def HexOrAddressExpr(s):
 
 def load_commands() -> None:
     # pylint: disable=import-outside-toplevel
+    import pwndbg.commands.ai
     import pwndbg.commands.argv
     import pwndbg.commands.aslr
     import pwndbg.commands.attachp
diff --git a/pwndbg/commands/ai.py b/pwndbg/commands/ai.py
new file mode 100644
index 000000000..5253f9c2a
--- /dev/null
+++ b/pwndbg/commands/ai.py
@@ -0,0 +1,267 @@
+"""
+This command sends information on the current debugging context to OpenAI's
+GPT-3 large language model and asks it a question supplied by the user. It then
+displays GPT-3's response to that question to the user.
+"""
+
+import argparse
+import json
+import os
+import re
+import textwrap
+
+import gdb
+import requests
+
+import pwndbg
+import pwndbg.color.message as M
+import pwndbg.commands
+from pwndbg.commands import CommandCategory
+from pwndbg.commands import context
+from pwndbg.gdblib import config
+from pwndbg.gdblib import regs as REGS
+
+config.add_param("ai-openai-api-key", "", "OpenAI API key")
+try:
+    config.ai_openai_api_key = os.environ["OPENAI_API_KEY"]
+except KeyError:
+    pass
+
+config.add_param(
+    "ai-history-size",
+    3,
+    "Maximum number of successive questions and answers to maintain in the prompt for the ai command.",
+)
+config.add_param(
+    "ai-stack-depth", 16, "Rows of stack context to include in the prompt for the ai command."
+)
+
+last_question = []
+last_answer = []
+last_pc = None
+last_command = None
+dummy = False
+
+
+def set_dummy_mode(d=True):
+    global dummy
+    dummy = d
+    return
+
+
+def build_prompt(question, command=None):
+    if command is not None:
+        return build_prompt_from_command(question, command)
+
+    decompile = False
+    ## First, get the current GDB context
+    ## Let's begin with the assembly near the current instruction
+    try:
+        asm_rows = pwndbg.gdblib.nearpc.nearpc(emulate=True, lines=16)
+        asm = "\n".join(asm_rows)
+    except Exception as e:
+        print(M.error(f"Error: {e}"))
+        asm = gdb.execute("x/16i $pc", to_string=True)
+    ## Next, let's get the registers
+    regs_rows = context.get_regs()
+    regs = "\n".join(regs_rows)
+    flags = None
+    try:
+        flags = gdb.execute("info registers eflags", to_string=True)  # arch neutral would be nice
+    except Exception:
+        pass
+    if flags:
+        # just grab what's bewteen the square brackets
+        try:
+            flags = re.search(r"\[(.*)\]", flags).group(1)
+        except Exception:
+            pass
+    ## Finally, let's get the stack
+    stack_rows = pwndbg.commands.telescope.telescope(
+        REGS.sp, to_string=True, count=config.ai_stack_depth
+    )
+    stack = "\n".join(stack_rows)
+    ## and the backtrace
+    trace = gdb.execute("bt", to_string=True)
+    ## the function arguments, if available
+    args = gdb.execute("info args", to_string=True)
+    ## and the local variables, if available
+    local_vars = None
+    ## and source information, if available
+    source = gdb.execute("list", to_string=True)
+    if len(source.split("\n")) < 3:
+        try:
+            source = pwndbg.ghidra.decompile()
+            decompile = True
+        except Exception as e:
+            pass
+    ## Now, let's build the prompt
+    prompt = "Consider the following context in the GDB debugger:\n"
+
+    if asm:
+        prompt += f"""These are the next assembly instructions to be executed:
+
+```
+{asm}
+```
+
+"""
+    if regs:
+        prompt += f"""Here are the registers, '*' indicates a recent change:
+
+```
+{regs}
+```
+
+"""
+    if flags:
+        prompt += f"""The flags {flags} are set.\n\n"""
+    if stack:
+        prompt += f"""Here is the stack:
+
+```
+{stack}
+```
+
+"""
+    if trace:
+        prompt += f"""Here is the backtrace:
+
+```
+{trace}
+```
+"""
+    if args and "No symbol table info available" not in args:
+        prompt += f"""Here are the function arguments:
+
+```
+{args}
+```
+"""
+
+    if local_vars and "No symbol table info available" not in local_vars:
+        prompt += f"""Here are the local variables:
+
+```
+{local_vars}
+```
+"""
+
+    if source:
+        prompt += f"""Here is the {'decompiled ' if decompile else ''}source code near the current instruction:
+
+```
+{source}
+```
+"""
+    return finish_prompt(prompt, question)
+
+
+def build_prompt_from_command(question, command):
+    prompt = (
+        f"""Running the command `{command}` in the GDB debugger yields the following output:\n"""
+    )
+    output = gdb.execute(command, to_string=True)
+    print(output)
+    prompt += f"""\n```\n{output}\n```\n\n"""
+    return finish_prompt(prompt, question)
+
+
+def strip_colors(text):
+    ## Now remove all ANSI color codes from the prompt
+    return re.sub(r"\x1b[^m]*m", "", text)
+
+
+def finish_prompt(prompt, question):
+    ## If the context hasn't changed, include the last question and answer
+    ## (we could add more of these, but there are length limitations on prompts)
+    for (q, a) in zip(last_question, last_answer):
+        prompt += f"""Question: {q}\n\nAnswer: {a}\n\n"""
+
+    prompt += f"""Question: {question}
+
+Answer: """
+
+    prompt = strip_colors(prompt)
+
+    return prompt
+
+
+def query_openai(prompt, model="text-davinci-003", max_tokens=100, temperature=0.0):
+    if dummy:
+        return f"""This is a dummy response for unit testing purposes.\nmodel = {model}, max_tokens = {max_tokens}, temperature = {temperature}\n\nPrompt:\n\n{prompt}"""
+    data = {"model": model, "max_tokens": max_tokens, "prompt": prompt, "temperature": temperature}
+    host = "api.openai.com"
+    path = "/v1/completions"
+    url = f"https://{host}{path}"
+    try:
+        r = requests.post(
+            url,
+            data=json.dumps(data),
+            headers={"Content-Type": "application/json"},
+            auth=("Bearer", config.ai_openai_api_key),
+        )
+        res = r.json()
+        return res["choices"][0]["text"]
+    except Exception as e:
+        print(M.error(f"Error sending query to OpenAI: {e}"))
+        return None
+
+
+parser = argparse.ArgumentParser(
+    description="Ask GPT-3 a question about the current debugging context."
+)
+parser.add_argument("question", nargs="+", type=str, help="The question to ask.")
+parser.add_argument(
+    "-M", "--model", default="text-davinci-003", type=str, help="The OpenAI model to use."
+)
+parser.add_argument("-t", "--temperature", default=0.5, type=float, help="The temperature to use.")
+parser.add_argument(
+    "-m", "--max-tokens", default=128, type=int, help="The maximum number of tokens to generate."
+)
+parser.add_argument("-v", "--verbose", action="store_true", help="Print the prompt and response.")
+parser.add_argument(
+    "-c",
+    "--command",
+    type=str,
+    default=None,
+    help="Run a command in the GDB debugger and ask a question about the output.",
+)
+
+
+@pwndbg.commands.OnlyWhenRunning
+@pwndbg.commands.ArgparsedCommand(parser, command_name="ai", category=CommandCategory.INTEGRATIONS)
+def ai(question, model, temperature, max_tokens, verbose, command=None) -> None:
+    # print the arguments
+    global last_question, last_answer, last_pc, last_command
+    if not config.ai_openai_api_key:
+        print(
+            "Please set ai_openai_api_key config parameter in your GDB init file or set the OPENAI_API_KEY environment variable"
+        )
+        return
+    question = " ".join(question).strip()
+    current_pc = gdb.execute("info reg $pc", to_string=True)
+    if current_pc == last_pc and command is None:
+        command = last_command
+    else:
+        last_command = command
+    if last_pc != current_pc or last_command != command:
+        last_question.clear()
+        last_answer.clear()
+
+    prompt = build_prompt(question, command)
+    if verbose:
+        print(M.notice(f"Sending this prompt to OpenAI:\n\n{prompt}"))
+    res = query_openai(prompt, model=model, max_tokens=max_tokens, temperature=temperature).strip()
+    last_question.append(question)
+    last_answer.append(res)
+    last_pc = current_pc
+    if len(last_question) > config.ai_history_size:
+        last_question.pop(0)
+        last_answer.pop(0)
+
+    term_width = os.get_terminal_size().columns
+    answer = textwrap.fill(res, term_width)
+    print(M.success(answer))
+
+    return
diff --git a/requirements.txt b/requirements.txt
index 877e6f755..c90a3eeb5 100644
--- a/requirements.txt
+++ b/requirements.txt
@@ -10,3 +10,5 @@ typing-extensions==4.3.0; python_version >= '3.7'
 typing-extensions==4.1.1; python_version < '3.7'
 unicorn==2.0.1.post1; python_version >= '3.7'
 unicorn==2.0.0rc7; python_version < '3.7'
+requests>=2.20.0
+types-requests>=2.20.0