diff --git a/.github/workflows/deploy.yml b/.github/workflows/deploy.yml
index e9e5967..9d2f106 100644
--- a/.github/workflows/deploy.yml
+++ b/.github/workflows/deploy.yml
@@ -1,31 +1,35 @@
-name: Deploy
+name: Poetry Deployment
 
 on:
   release:
     types: [published]
 
 jobs:
-  deploy:
+  all:
 
-    runs-on: ubuntu-latest
+    strategy:
+      fail-fast: true
+      matrix:
+        python-version: ["3.8"]
+        poetry-version: ["1.7"]
+        os: ["ubuntu-latest"]
 
+    runs-on: ${{ matrix.os }}
     steps:
-    - uses: actions/checkout@v2
+    - uses: actions/checkout@v3
 
     - name: Set up Python
-      uses: actions/setup-python@v2
+      uses: actions/setup-python@v4
       with:
-        python-version: '3.x'
+        python-version: ${{ matrix.python-version }}
 
-    - name: Install dependencies
-      run: |
-        python -m pip install --upgrade pip
-        pip install build
-    - name: Build package
-      run: python -m build
+    - name: Run Poetry Image
+      uses: abatilo/actions-poetry@v2
+      with:
+        poetry-version: ${{ matrix.poetry-version }}
+
+    - name: Configure PyPI
+      run: poetry config pypi-token.pypi ${{ secrets.PYPI_API_TOKEN }}
 
     - name: Publish package
-      uses: pypa/gh-action-pypi-publish@27b31702a0e7fc50959f5ad993c78deac1bdfc29
-      with:
-        user: __token__
-        password: ${{ secrets.PYPI_API_TOKEN }}
+      run: poetry publish --build --no-interaction
diff --git a/.github/workflows/test.yml b/.github/workflows/test.yml
index 5c98ed2..8b57e03 100644
--- a/.github/workflows/test.yml
+++ b/.github/workflows/test.yml
@@ -1,28 +1,35 @@
-name: PyTest
+name: Poetry Testing
 
 on:
   pull_request:
     branches: [main]
 
 jobs:
-  test:
+  all:
 
-    runs-on: ubuntu-latest
     strategy:
+      fail-fast: true
       matrix:
-        python-version: ["3.8", "3.9", "3.10"]
+        python-version: ["3.11", "3.12"]
+        poetry-version: ["1.4"]
+        os: [ubuntu-latest, macos-latest, windows-latest]
 
+    runs-on: ${{ matrix.os }}
     steps:
-    - uses: actions/checkout@v2
+    - uses: actions/checkout@v3
 
     - name: Set up Python
-      uses: actions/setup-python@v2
+      uses: actions/setup-python@v4
       with:
         python-version: ${{ matrix.python-version }}
 
-    - name: Install dependencies
-      run: |
-        python -m pip install --upgrade pip
-        if [ -f requirements.txt ]; then pip install -r requirements.txt; fi
+    - name: Run Poetry Image
+      uses: abatilo/actions-poetry@v2
+      with:
+        poetry-version: ${{ matrix.poetry-version }}
+
+    - name: Install Dependencies
+      run: poetry install
+
     - name: PyTest
-      run: python -m pytest
\ No newline at end of file
+      run: poetry run pytest
diff --git a/MANIFEST.in b/MANIFEST.in
deleted file mode 100644
index 2ff425c..0000000
--- a/MANIFEST.in
+++ /dev/null
@@ -1 +0,0 @@
-recursive-include imagetitler/assets *
diff --git a/README.md b/README.md
index caa7537..7d5a47b 100644
--- a/README.md
+++ b/README.md
@@ -78,3 +78,14 @@ Here's a description of all the option used in the samples above.
 | --tier, -r | Choose between "free" (silver) or "premium" (gold) | Adds a border color to the title |
 | --title, -t | Any string | Overrides the automatic title feature |
 | --no_title, -n | | Do not add title |
+
+## Python Version Compatibility
+
+As this utility has grown and changed, it has also changed its
+support for different versions of Python.
+
+| Python                 | 3.12 | 3.11 | 3.10 | 3.9 | 3.8 |
+| ---------------------- | ---- | ---- | ---- | --- | --- |
+| image-titler >= 2.5    | yes  | yes  |      |     |     |
+| image-titler 1.8 - 2.5 |      |      | yes  | yes | yes |
+| image-titler <= 1.8    |      |      |      |     |     |
diff --git a/imagetitler/__init__.py b/imagetitler/__init__.py
index faf1664..3e02c00 100644
--- a/imagetitler/__init__.py
+++ b/imagetitler/__init__.py
@@ -1 +1,6 @@
-__version__ = "2.4.0"
\ No newline at end of file
+import tomllib
+
+with open("pyproject.toml", "rb") as f:
+    _META = tomllib.load(f)
+
+__version__ = _META["tool"]["poetry"]["version"]
diff --git a/imagetitler/draw.py b/imagetitler/draw.py
index 5614586..737fcca 100644
--- a/imagetitler/draw.py
+++ b/imagetitler/draw.py
@@ -237,7 +237,7 @@ def _get_appropriate_font_size(**kwargs) -> ImageFont:
     font = font if font else DEFAULT_FONT
     title = kwargs.get(KEY_TITLE)
     font_size = 12
-    while ImageFont.truetype(font, font_size).getsize(title)[1] < bar_height - 10:
+    while ImageFont.truetype(font, font_size).getbbox(title)[3] < bar_height - 10:
         font_size += 1
     return ImageFont.truetype(font, font_size)
 
diff --git a/poetry.lock b/poetry.lock
new file mode 100644
index 0000000..adb7af7
--- /dev/null
+++ b/poetry.lock
@@ -0,0 +1,713 @@
+# This file is automatically @generated by Poetry 1.7.1 and should not be changed by hand.
+
+[[package]]
+name = "colorama"
+version = "0.4.6"
+description = "Cross-platform colored terminal text."
+optional = false
+python-versions = "!=3.0.*,!=3.1.*,!=3.2.*,!=3.3.*,!=3.4.*,!=3.5.*,!=3.6.*,>=2.7"
+files = [
+    {file = "colorama-0.4.6-py2.py3-none-any.whl", hash = "sha256:4f1d9991f5acc0ca119f9d443620b77f9d6b33703e51011c16baf57afb285fc6"},
+    {file = "colorama-0.4.6.tar.gz", hash = "sha256:08695f5cb7ed6e0531a20572697297273c47b8cae5a63ffc6d6ed5c201be6e44"},
+]
+
+[[package]]
+name = "contourpy"
+version = "1.2.0"
+description = "Python library for calculating contours of 2D quadrilateral grids"
+optional = false
+python-versions = ">=3.9"
+files = [
+    {file = "contourpy-1.2.0-cp310-cp310-macosx_10_9_x86_64.whl", hash = "sha256:0274c1cb63625972c0c007ab14dd9ba9e199c36ae1a231ce45d725cbcbfd10a8"},
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+    {file = "contourpy-1.2.0.tar.gz", hash = "sha256:171f311cb758de7da13fc53af221ae47a5877be5a0843a9fe150818c51ed276a"},
+]
+
+[package.dependencies]
+numpy = ">=1.20,<2.0"
+
+[package.extras]
+bokeh = ["bokeh", "selenium"]
+docs = ["furo", "sphinx (>=7.2)", "sphinx-copybutton"]
+mypy = ["contourpy[bokeh,docs]", "docutils-stubs", "mypy (==1.6.1)", "types-Pillow"]
+test = ["Pillow", "contourpy[test-no-images]", "matplotlib"]
+test-no-images = ["pytest", "pytest-cov", "pytest-xdist", "wurlitzer"]
+
+[[package]]
+name = "coverage"
+version = "7.4.0"
+description = "Code coverage measurement for Python"
+optional = false
+python-versions = ">=3.8"
+files = [
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diff --git a/pyproject.toml b/pyproject.toml
new file mode 100644
index 0000000..70e9efb
--- /dev/null
+++ b/pyproject.toml
@@ -0,0 +1,30 @@
+[tool.poetry]
+name = "image-titler"
+version = "2.5.0"
+description = "An image processing utility which provides options for generating thumbnails for various social media platforms."
+authors = ["Jeremy Grifski <jeremy.grifski@therenegadecoder.com>"]
+license = "GPL-3.0-or-later"
+readme = "README.md"
+repository = "https://github.com/TheRenegadeCoder/image-titler"
+packages = [{include = "imagetitler"}]
+
+[tool.poetry.dependencies]
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+pathvalidate = "^2.0"
+piexif = "^1.0"
+matplotlib = "^3.0"
+
+[tool.poetry.group.test.dependencies]
+pytest = "*"
+pytest-cov = "*"
+
+[tool.poetry.scripts]
+image-titler = "scripts.cli:main"
+image_titler = "scripts.cli:main"
+image-titler-gui = "scripts.gui:main"
+
+[build-system]
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+build-backend = "poetry.core.masonry.api"
diff --git a/requirements.txt b/requirements.txt
deleted file mode 100644
index ff3dc70..0000000
--- a/requirements.txt
+++ /dev/null
@@ -1,7 +0,0 @@
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-pillow>=9.0.0
-pathvalidate>=2.0.0
-piexif>=1.0.0
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diff --git a/samples/v2.4.0/23-tech-topics-to-tackle-v2-4-0.jpg b/samples/v2.4.0/23-tech-topics-to-tackle-v2-4-0.jpg
index b2b8c90..d40b9d0 100644
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diff --git a/setup.py b/setup.py
deleted file mode 100644
index 38907aa..0000000
--- a/setup.py
+++ /dev/null
@@ -1,43 +0,0 @@
-import setuptools
-
-from imagetitler import __version__
-
-with open("README.md", "r") as fh:
-    long_description = fh.read()
-
-setuptools.setup(
-    name="image-titler",
-    version=__version__,
-    author="The Renegade Coder",
-    author_email="jeremy.grifski@therenegadecoder.com",
-    description="An image processing utility which provides options for generating thumbnails for various social media platforms.",
-    long_description=long_description,
-    long_description_content_type="text/markdown",
-    url="https://github.com/TheRenegadeCoder/image-titler",
-    packages=setuptools.find_packages(),
-    include_package_data=True,
-    python_requires=">=3.8",
-    entry_points={
-        "console_scripts": [
-            'image-titler = scripts.cli:main',
-            'image_titler = scripts.cli:main',  # For backwards compatibility
-        ],
-        "gui_scripts": [
-            'image-titler-gui = scripts.gui:main',
-        ]
-    },
-    classifiers=[
-        "Programming Language :: Python :: 3.8",
-        "Programming Language :: Python :: 3.9",
-        "Programming Language :: Python :: 3.10",
-        "License :: OSI Approved :: GNU General Public License v3 (GPLv3)",
-        "Operating System :: OS Independent",
-    ],
-    install_requires=[
-        'titlecase>=2.0',
-        'pillow>=9.0.0',
-        'pathvalidate>=2.0.0',
-        'piexif>=1.0.0',
-        'matplotlib>=3.0.0'
-    ],
-)
diff --git a/tests/__init__.py b/tests/__init__.py
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