diff --git a/bob/.exercism/config.json b/bob/.exercism/config.json
new file mode 100644
index 0000000..ec0fc61
--- /dev/null
+++ b/bob/.exercism/config.json
@@ -0,0 +1,47 @@
+{
+  "authors": [],
+  "contributors": [
+    "0xae",
+    "aldraco",
+    "atg-abhishek",
+    "austinlyons",
+    "behrtam",
+    "BethanyG",
+    "cmccandless",
+    "cypher",
+    "Dog",
+    "etrepum",
+    "ikhadykin",
+    "janetriley",
+    "jremmen",
+    "koljakube",
+    "kytrinyx",
+    "lowks",
+    "lucasdpau",
+    "miketamis",
+    "N-Parsons",
+    "patricksjackson",
+    "pheanex",
+    "sdublish",
+    "sjakobi",
+    "stonemirror",
+    "thenigan",
+    "thomasjpfan",
+    "tqa236",
+    "yawpitch"
+  ],
+  "files": {
+    "solution": [
+      "bob.py"
+    ],
+    "test": [
+      "bob_test.py"
+    ],
+    "example": [
+      ".meta/example.py"
+    ]
+  },
+  "blurb": "Bob is a lackadaisical teenager. In conversation, his responses are very limited.",
+  "source": "Inspired by the 'Deaf Grandma' exercise in Chris Pine's Learn to Program tutorial.",
+  "source_url": "https://pine.fm/LearnToProgram/?Chapter=06"
+}
diff --git a/bob/.exercism/metadata.json b/bob/.exercism/metadata.json
new file mode 100644
index 0000000..86f2316
--- /dev/null
+++ b/bob/.exercism/metadata.json
@@ -0,0 +1 @@
+{"track":"python","exercise":"bob","id":"1d2ff6c6201846348f2afd8ab38f6e5f","url":"https://exercism.org/tracks/python/exercises/bob","handle":"myFirstCode","is_requester":true,"auto_approve":false}
\ No newline at end of file
diff --git a/bob/HELP.md b/bob/HELP.md
new file mode 100644
index 0000000..c92dfd6
--- /dev/null
+++ b/bob/HELP.md
@@ -0,0 +1,130 @@
+# Help
+
+## Running the tests
+
+We use [pytest][pytest: Getting Started Guide] as our website test runner.
+You will need to install `pytest` on your development machine if you want to run tests for the Python track locally.
+You should also install the following `pytest` plugins:
+
+- [pytest-cache][pytest-cache]
+- [pytest-subtests][pytest-subtests]
+
+Extended information can be found in our website [Python testing guide][Python track tests page].
+
+
+### Running Tests
+
+To run the included tests, navigate to the folder where the exercise is stored using `cd` in your terminal (_replace `{exercise-folder-location}` below with your path_).
+Test files usually end in `_test.py`, and are the same tests that run on the website when a solution is uploaded.
+
+Linux/MacOS
+```bash
+$ cd {path/to/exercise-folder-location}
+```
+
+Windows
+```powershell
+PS C:\Users\foobar> cd {path\to\exercise-folder-location}
+```
+
+<br>
+
+Next, run the `pytest` command in your terminal, replacing `{exercise_test.py}` with the name of the test file:
+
+Linux/MacOS
+```bash
+$ python3 -m pytest -o markers=task {exercise_test.py}
+==================== 7 passed in 0.08s ====================
+```
+
+Windows
+```powershell
+PS C:\Users\foobar> py -m pytest -o markers=task {exercise_test.py}
+==================== 7 passed in 0.08s ====================
+```
+
+
+### Common options
+- `-o` : override default `pytest.ini` (_you can use this to avoid marker warnings_)
+- `-v` : enable verbose output.
+- `-x` : stop running tests on first failure.
+- `--ff` : run failures from previous test before running other test cases.
+
+For additional options, use `python3 -m pytest -h` or `py -m pytest -h`.
+
+
+### Fixing warnings
+
+If you do not use `pytest -o markers=task` when invoking `pytest`, you might receive a `PytestUnknownMarkWarning` for tests that use our new syntax:
+
+```bash
+PytestUnknownMarkWarning: Unknown pytest.mark.task - is this a typo?  You can register custom marks to avoid this warning - for details, see https://docs.pytest.org/en/stable/mark.html
+```
+
+To avoid typing `pytest -o markers=task` for every test you run, you can use a `pytest.ini` configuration file.
+We have made one that can be downloaded from the top level of the Python track directory: [pytest.ini][pytest.ini].
+
+You can also create your own `pytest.ini` file with the following content:
+
+```ini
+[pytest]
+markers =
+    task: A concept exercise task.
+```
+
+Placing the `pytest.ini` file in the _root_ or _working_ directory for your Python track exercises will register the marks and stop the warnings.
+More information on pytest marks can be found in the `pytest` documentation on [marking test functions][pytest: marking test functions with attributes] and the `pytest` documentation on [working with custom markers][pytest: working with custom markers].
+
+Information on customizing pytest configurations can be found in the `pytest` documentation on [configuration file formats][pytest: configuration file formats].
+
+
+### Extending your IDE or Code Editor
+
+Many IDEs and code editors have built-in support for using `pytest` and other code quality tools.
+Some community-sourced options can be found on our [Python track tools page][Python track tools page].
+
+[Pytest: Getting Started Guide]: https://docs.pytest.org/en/latest/getting-started.html
+[Python track tools page]: https://exercism.org/docs/tracks/python/tools
+[Python track tests page]: https://exercism.org/docs/tracks/python/tests
+[pytest-cache]:http://pythonhosted.org/pytest-cache/
+[pytest-subtests]:https://github.com/pytest-dev/pytest-subtests
+[pytest.ini]: https://github.com/exercism/python/blob/main/pytest.ini
+[pytest: configuration file formats]: https://docs.pytest.org/en/6.2.x/customize.html#configuration-file-formats
+[pytest: marking test functions with attributes]: https://docs.pytest.org/en/6.2.x/mark.html#raising-errors-on-unknown-marks
+[pytest: working with custom markers]: https://docs.pytest.org/en/6.2.x/example/markers.html#working-with-custom-markers
+
+## Submitting your solution
+
+You can submit your solution using the `exercism submit bob.py` command.
+This command will upload your solution to the Exercism website and print the solution page's URL.
+
+It's possible to submit an incomplete solution which allows you to:
+
+- See how others have completed the exercise
+- Request help from a mentor
+
+## Need to get help?
+
+If you'd like help solving the exercise, check the following pages:
+
+- The [Python track's documentation](https://exercism.org/docs/tracks/python)
+- The [Python track's programming category on the forum](https://forum.exercism.org/c/programming/python)
+- [Exercism's programming category on the forum](https://forum.exercism.org/c/programming/5)
+- The [Frequently Asked Questions](https://exercism.org/docs/using/faqs)
+
+Should those resources not suffice, you could submit your (incomplete) solution to request mentoring.
+
+Below are some resources for getting help if you run into trouble:
+
+- [The PSF](https://www.python.org) hosts Python downloads, documentation, and community resources.
+- [The Exercism Community on Discord](https://exercism.org/r/discord)
+- [Python Community on Discord](https://pythondiscord.com/) is a very helpful and active community.
+- [/r/learnpython/](https://www.reddit.com/r/learnpython/) is a subreddit designed for Python learners.
+- [#python on Libera.chat](https://www.python.org/community/irc/) this is where the core developers for the language hang out and get work done.
+- [Python Community Forums](https://discuss.python.org/)
+- [Free Code Camp Community Forums](https://forum.freecodecamp.org/)
+- [CodeNewbie Community Help Tag](https://community.codenewbie.org/t/help)
+- [Pythontutor](http://pythontutor.com/) for stepping through small code snippets visually.
+
+Additionally, [StackOverflow](http://stackoverflow.com/questions/tagged/python) is a good spot to search for your problem/question to see if it has been answered already.
+ If not - you can always [ask](https://stackoverflow.com/help/how-to-ask) or [answer](https://stackoverflow.com/help/how-to-answer) someone else's question.
\ No newline at end of file
diff --git a/bob/README.md b/bob/README.md
new file mode 100644
index 0000000..823897d
--- /dev/null
+++ b/bob/README.md
@@ -0,0 +1,72 @@
+# Bob
+
+Welcome to Bob on Exercism's Python Track.
+If you need help running the tests or submitting your code, check out `HELP.md`.
+
+## Introduction
+
+Bob is a [lackadaisical][] teenager.
+He likes to think that he's very cool.
+And he definitely doesn't get excited about things.
+That wouldn't be cool.
+
+When people talk to him, his responses are pretty limited.
+
+[lackadaisical]: https://www.collinsdictionary.com/dictionary/english/lackadaisical
+
+## Instructions
+
+Your task is to determine what Bob will reply to someone when they say something to him or ask him a question.
+
+Bob only ever answers one of five things:
+
+- **"Sure."**
+  This is his response if you ask him a question, such as "How are you?"
+  The convention used for questions is that it ends with a question mark.
+- **"Whoa, chill out!"**
+  This is his answer if you YELL AT HIM.
+  The convention used for yelling is ALL CAPITAL LETTERS.
+- **"Calm down, I know what I'm doing!"**
+  This is what he says if you yell a question at him.
+- **"Fine. Be that way!"**
+  This is how he responds to silence.
+  The convention used for silence is nothing, or various combinations of whitespace characters.
+- **"Whatever."**
+  This is what he answers to anything else.
+
+## Source
+
+### Contributed to by
+
+- @0xae
+- @aldraco
+- @atg-abhishek
+- @austinlyons
+- @behrtam
+- @BethanyG
+- @cmccandless
+- @cypher
+- @Dog
+- @etrepum
+- @ikhadykin
+- @janetriley
+- @jremmen
+- @koljakube
+- @kytrinyx
+- @lowks
+- @lucasdpau
+- @miketamis
+- @N-Parsons
+- @patricksjackson
+- @pheanex
+- @sdublish
+- @sjakobi
+- @stonemirror
+- @thenigan
+- @thomasjpfan
+- @tqa236
+- @yawpitch
+
+### Based on
+
+Inspired by the 'Deaf Grandma' exercise in Chris Pine's Learn to Program tutorial. - https://pine.fm/LearnToProgram/?Chapter=06
\ No newline at end of file
diff --git a/bob/bob.py b/bob/bob.py
new file mode 100644
index 0000000..f4e084e
--- /dev/null
+++ b/bob/bob.py
@@ -0,0 +1,53 @@
+"""
+Your task is to determine what Bob will reply to someone when they say something
+to him or ask him a question.
+
+Bob only ever answers one of five things:
+
+- "Sure." This is his response if you ask him a question, such as "How are you?"
+  The convention used for questions is that it ends with a question mark.
+- "Whoa, chill out!" This is his answer if you YELL AT HIM.
+  The convention used for yelling is ALL CAPITAL LETTERS.
+- "Calm down, I know what I'm doing!" This is what he says if you yell a question at him.
+- "Fine. Be that way!" This is how he responds to silence.
+  The convention used for silence is nothing, or various combinations of whitespace characters.
+- "Whatever." This is what he answers to anything else.
+"""
+
+
+def response(hey_bob: str) -> str:
+    """
+    Determine what Bob will reply to someone when they say something to him or ask him a question.
+
+    :param hey_bob: str
+    :return: str
+    """
+    # Remove whitespaces
+    hey_bob = hey_bob.strip()
+    # Empty string -> responds to silence.
+    if not hey_bob:
+        return "Fine. Be that way!"
+
+    # Yell at Bob
+    if hey_bob == hey_bob.upper() and any(char.isalpha() for char in hey_bob):
+        # Yell a question
+        if is_question(hey_bob):
+            return "Calm down, I know what I'm doing!"
+        return "Whoa, chill out!"
+
+    # Ask question
+    if is_question(hey_bob):
+        return "Sure."
+
+    # Anything else.
+    return "Whatever."
+
+
+def is_question(hey_bob: str) -> bool:
+    """
+    Determine if you ask/yell a question.
+
+    :param hey_bob: str
+    :return: bool
+    """
+    return hey_bob[-1] == "?"
diff --git a/bob/bob_test.py b/bob/bob_test.py
new file mode 100644
index 0000000..c74dfc0
--- /dev/null
+++ b/bob/bob_test.py
@@ -0,0 +1,103 @@
+# pylint: disable=C0114, C0115, C0116, R0904
+
+# These tests are auto-generated with test data from:
+# https://github.com/exercism/problem-specifications/tree/main/exercises/bob/canonical-data.json
+# File last updated on 2025-01-10
+
+import unittest
+
+from bob import (
+    response,
+)
+
+
+class BobTest(unittest.TestCase):
+    def test_stating_something(self):
+        self.assertEqual(response("Tom-ay-to, tom-aaaah-to."), "Whatever.")
+
+    def test_shouting(self):
+        self.assertEqual(response("WATCH OUT!"), "Whoa, chill out!")
+
+    def test_shouting_gibberish(self):
+        self.assertEqual(response("FCECDFCAAB"), "Whoa, chill out!")
+
+    def test_asking_a_question(self):
+        self.assertEqual(
+            response("Does this cryogenic chamber make me look fat?"), "Sure."
+        )
+
+    def test_asking_a_numeric_question(self):
+        self.assertEqual(response("You are, what, like 15?"), "Sure.")
+
+    def test_asking_gibberish(self):
+        self.assertEqual(response("fffbbcbeab?"), "Sure.")
+
+    def test_talking_forcefully(self):
+        self.assertEqual(response("Hi there!"), "Whatever.")
+
+    def test_using_acronyms_in_regular_speech(self):
+        self.assertEqual(
+            response("It's OK if you don't want to go work for NASA."), "Whatever."
+        )
+
+    def test_forceful_question(self):
+        self.assertEqual(
+            response("WHAT'S GOING ON?"), "Calm down, I know what I'm doing!"
+        )
+
+    def test_shouting_numbers(self):
+        self.assertEqual(response("1, 2, 3 GO!"), "Whoa, chill out!")
+
+    def test_no_letters(self):
+        self.assertEqual(response("1, 2, 3"), "Whatever.")
+
+    def test_question_with_no_letters(self):
+        self.assertEqual(response("4?"), "Sure.")
+
+    def test_shouting_with_special_characters(self):
+        self.assertEqual(
+            response("ZOMG THE %^*@#$(*^ ZOMBIES ARE COMING!!11!!1!"),
+            "Whoa, chill out!",
+        )
+
+    def test_shouting_with_no_exclamation_mark(self):
+        self.assertEqual(response("I HATE THE DENTIST"), "Whoa, chill out!")
+
+    def test_statement_containing_question_mark(self):
+        self.assertEqual(response("Ending with ? means a question."), "Whatever.")
+
+    def test_non_letters_with_question(self):
+        self.assertEqual(response(":) ?"), "Sure.")
+
+    def test_prattling_on(self):
+        self.assertEqual(response("Wait! Hang on. Are you going to be OK?"), "Sure.")
+
+    def test_silence(self):
+        self.assertEqual(response(""), "Fine. Be that way!")
+
+    def test_prolonged_silence(self):
+        self.assertEqual(response("          "), "Fine. Be that way!")
+
+    def test_alternate_silence(self):
+        self.assertEqual(response("\t\t\t\t\t\t\t\t\t\t"), "Fine. Be that way!")
+
+    def test_starting_with_whitespace(self):
+        self.assertEqual(response("         hmmmmmmm..."), "Whatever.")
+
+    def test_ending_with_whitespace(self):
+        self.assertEqual(
+            response("Okay if like my  spacebar  quite a bit?   "), "Sure."
+        )
+
+    def test_other_whitespace(self):
+        self.assertEqual(response("\n\r \t"), "Fine. Be that way!")
+
+    def test_non_question_ending_with_whitespace(self):
+        self.assertEqual(
+            response("This is a statement ending with whitespace      "), "Whatever."
+        )
+
+    def test_multiple_line_question(self):
+        self.assertEqual(
+            response("\nDoes this cryogenic chamber make\n me look fat?"), "Sure."
+        )
diff --git a/solutions/python/bob/1/bob.py b/solutions/python/bob/1/bob.py
new file mode 100644
index 0000000..79b79b2
--- /dev/null
+++ b/solutions/python/bob/1/bob.py
@@ -0,0 +1,50 @@
+"""
+Your task is to determine what Bob will reply to someone when they say something to him or ask him a question.
+
+Bob only ever answers one of five things:
+
+- "Sure." This is his response if you ask him a question, such as "How are you?"
+  The convention used for questions is that it ends with a question mark.
+- "Whoa, chill out!" This is his answer if you YELL AT HIM.
+  The convention used for yelling is ALL CAPITAL LETTERS.
+- "Calm down, I know what I'm doing!" This is what he says if you yell a question at him.
+- "Fine. Be that way!" This is how he responds to silence.
+  The convention used for silence is nothing, or various combinations of whitespace characters.
+- "Whatever." This is what he answers to anything else.
+"""
+
+
+def response(hey_bob: str) -> str:
+    """
+    Determine what Bob will reply to someone when they say something to him or ask him a question.
+
+    :param hey_bob: str
+    :return: str
+    """
+    # Empty string -> responds to silence.
+    if not hey_bob.strip():
+        return "Fine. Be that way!"
+
+    # Yell at Bob
+    if hey_bob == hey_bob.upper() and any(char.isalpha() for char in hey_bob):
+        # Yell a question
+        if is_question(hey_bob):
+            return "Calm down, I know what I'm doing!"
+        return "Whoa, chill out!"
+
+    # Ask question
+    if is_question(hey_bob):
+        return "Sure."
+
+    # Anything else.
+    return "Whatever."
+
+
+def is_question(hey_bob: str) -> bool:
+    """
+    Determine if you ask/yell a question.
+
+    :param hey_bob: str
+    :return: bool
+    """
+    return "?" in hey_bob and hey_bob.strip()[-1] == '?'