diff --git a/.githooks/pre-push b/.githooks/pre-push
index ba7f5ac86..cff188e15 100755
--- a/.githooks/pre-push
+++ b/.githooks/pre-push
@@ -4,24 +4,59 @@
 REPO_ROOT="$(git rev-parse --show-toplevel)"
 GITHOOKS_DIR="$REPO_ROOT/.githooks"
 
+# Track failures
+FAILED=0
+
+echo "========================================"
+echo "  Pre-Push Checks"
+echo "========================================"
+echo
+
 # Check for changes in Python files
-python_changed_files=($(git diff --name-only --diff-filter=ACM | grep '^python/lib/sift_client/' || true))
+# Compare against the remote branch being pushed to
+python_changed_files=($(git diff --name-only --diff-filter=ACM @{upstream}... | grep '^python/' || true))
 
+echo "→ Python files changed:"
 if [[ -n "$python_changed_files" ]]; then
-    echo "Python files changed, running Python formatting and linting..."
-    bash "$GITHOOKS_DIR/pre-push-python/fmt-lint.sh"
+    echo "  ${python_changed_files[*]}"
+    echo
+    echo "  [1/3] Formatting and linting..."
+    bash "$GITHOOKS_DIR/pre-push-python/fmt-lint.sh" || FAILED=1
     
-    echo "Running Python stub checks..."
-    bash "$GITHOOKS_DIR/pre-push-python/stubs.sh"
+    echo "  [2/3] Stub generation..."
+    bash "$GITHOOKS_DIR/pre-push-python/stubs.sh" || FAILED=1
+    
+    echo "  [3/3] Extras validation..."
+    bash "$GITHOOKS_DIR/pre-push-python/extras.sh" || FAILED=1
+    echo
+else
+    echo "  (none)"
+    echo
 fi
 
 # Check for changes in Rust bindings files
-bindings_changed_files=($(git diff --name-only --diff-filter=ACM | grep '^rust/crates/sift_stream_bindings/src/' || true))
+bindings_changed_files=($(git diff --name-only --diff-filter=ACM @{upstream}... | grep '^rust/crates/sift_stream_bindings/src/' || true))
 
+echo "→ Rust binding files changed:"
 if [[ -n "$bindings_changed_files" ]]; then
-    echo "Rust bindings files changed, running Rust stub checks..."
-    bash "$GITHOOKS_DIR/pre-push-rust/stubs.sh"
+    echo "  ${bindings_changed_files[*]}"
+    echo
+    echo "  [1/1] Stub generation..."
+    bash "$GITHOOKS_DIR/pre-push-rust/stubs.sh" || FAILED=1
+    echo
+else
+    echo "  (none)"
+    echo
 fi
 
-echo "Pre-push checks completed successfully."
+if [[ $FAILED -eq 1 ]]; then
+    echo "========================================"
+    echo "  ✗ Some checks failed"
+    echo "========================================"
+    exit 1
+else
+    echo "========================================"
+    echo "  ✓ All checks passed"
+    echo "========================================"
+fi
 
diff --git a/.githooks/pre-push-python/extras.sh b/.githooks/pre-push-python/extras.sh
new file mode 100755
index 000000000..56cb00620
--- /dev/null
+++ b/.githooks/pre-push-python/extras.sh
@@ -0,0 +1,37 @@
+# ensure generated pyproject.toml extras are up-to-date
+
+# Store the root directory of the repository
+REPO_ROOT="$(git rev-parse --show-toplevel)"
+PYTHON_DIR="$REPO_ROOT/python"
+PYPROJECT_FILE="$PYTHON_DIR/pyproject.toml"
+
+# Function to check if pyproject.toml has changed
+check_extras_changes() {
+    local target_path="$1"
+    local changed_files=$(git status --porcelain "$target_path" || true)
+
+    if [ -n "$changed_files" ]; then
+        echo "     ❌ ERROR: Generated extras are not up-to-date:"
+        echo "$changed_files" | sed 's/^/       /'
+        echo "     Please commit these changes before pushing."
+        exit 1
+    fi
+}
+
+# Function to generate Python extras
+generate_python_extras() {
+    echo "     → Generating extras..."
+    cd "$PYTHON_DIR"
+
+    if [[ ! -d "$PYTHON_DIR/venv" ]]; then
+        echo "     → Running bootstrap script..."
+        bash ./scripts/dev bootstrap
+    fi
+
+    bash ./scripts/dev gen-extras
+    check_extras_changes "$PYPROJECT_FILE"
+}
+
+generate_python_extras
+
+echo "     ✓ Extras are up-to-date"
diff --git a/.githooks/pre-push-python/fmt-lint.sh b/.githooks/pre-push-python/fmt-lint.sh
index 575a4475b..f112c7f09 100644
--- a/.githooks/pre-push-python/fmt-lint.sh
+++ b/.githooks/pre-push-python/fmt-lint.sh
@@ -6,17 +6,15 @@ set -e
 REPO_ROOT="$(git rev-parse --show-toplevel)"
 PYTHON_DIR="$REPO_ROOT/python"
 
-echo "Running Python formatting and linting with --fix..."
-
 # Change to Python directory
 cd "$PYTHON_DIR"
 
 # Run ruff format (formatter)
-echo "Running ruff format..."
+echo "     → Running ruff format..."
 bash ./scripts/dev fmt
 
 # Run ruff check with --fix (linter)
-echo "Running ruff check --fix..."
+echo "     → Running ruff check --fix..."
 bash ./scripts/dev lint-fix
 
 # Check if any files were modified by formatting/linting
@@ -25,11 +23,11 @@ changed_files=$(git status --porcelain python/lib/sift_client/ | grep -E '\.py$'
 
 if [ -n "$changed_files" ]; then
     echo ""
-    echo "ERROR: Formatting/linting made changes to the following files:"
-    echo "$changed_files"
+    echo "     ❌ ERROR: Formatting/linting made changes:"
+    echo "$changed_files" | sed 's/^/       /'
     echo ""
-    echo "Please commit these changes before pushing."
+    echo "     Please commit these changes before pushing."
     exit 1
 fi
 
-echo "Python formatting and linting completed successfully."
+echo "     ✓ Formatting and linting passed"
diff --git a/.githooks/pre-push-python/stubs.sh b/.githooks/pre-push-python/stubs.sh
index 42d6d712b..9ee86fb42 100644
--- a/.githooks/pre-push-python/stubs.sh
+++ b/.githooks/pre-push-python/stubs.sh
@@ -11,19 +11,20 @@ check_stub_changes() {
     local changed_files=$(git status --porcelain "$target_path" | grep -E '\.pyi$' || true)
 
     if [ -n "$changed_files" ]; then
-        echo "ERROR: Generated python stubs are not up-to-date. Please commit the changed files:"
-        echo "$changed_files"
+        echo "     ❌ ERROR: Generated stubs are not up-to-date:"
+        echo "$changed_files" | sed 's/^/       /'
+        echo "     Please commit these changes before pushing."
         exit 1
     fi
 }
 
 # Function to generate Python stubs
 generate_python_stubs() {
-    echo "Generating Python stubs..."
+    echo "     → Generating stubs..."
     cd "$PYTHON_DIR"
 
     if [[ ! -d "$PYTHON_DIR/venv" ]]; then
-        echo "Running bootstrap script..."
+        echo "     → Running bootstrap script..."
         bash ./scripts/dev bootstrap
     fi
 
@@ -33,4 +34,4 @@ generate_python_stubs() {
 
 generate_python_stubs
 
-echo "All stubs are up-to-date."
\ No newline at end of file
+echo "     ✓ Stubs are up-to-date"
\ No newline at end of file
diff --git a/.githooks/pre-push-rust/stubs.sh b/.githooks/pre-push-rust/stubs.sh
index 1af106713..980750c9d 100644
--- a/.githooks/pre-push-rust/stubs.sh
+++ b/.githooks/pre-push-rust/stubs.sh
@@ -10,15 +10,16 @@ check_stub_changes() {
     local changed_files=$(git status --porcelain "$target_path" | grep -E '\.pyi$' || true)
 
     if [ -n "$changed_files" ]; then
-        echo "ERROR: Generated python stubs are not up-to-date. Please commit the changed files:"
-        echo "$changed_files"
+        echo "     ❌ ERROR: Generated stubs are not up-to-date:"
+        echo "$changed_files" | sed 's/^/       /'
+        echo "     Please commit these changes before pushing."
         exit 1
     fi
 }
 
 # Function to generate bindings stubs
 generate_bindings_stubs() {
-    echo "Generating bindings stubs..."
+    echo "     → Generating stubs..."
     cd "$BINDINGS_DIR"
     cargo run --bin stub_gen
 
@@ -29,4 +30,4 @@ generate_bindings_stubs() {
 
 generate_bindings_stubs
 
-echo "All stubs are up-to-date."
\ No newline at end of file
+echo "     ✓ Stubs are up-to-date"
\ No newline at end of file
diff --git a/.github/workflows/python_build_docs.yml b/.github/workflows/python_build_docs.yml
index 912cb3d33..a654ea3d7 100644
--- a/.github/workflows/python_build_docs.yml
+++ b/.github/workflows/python_build_docs.yml
@@ -2,7 +2,7 @@ name: Build and Deploy Python Docs (Dev)
 
 on:
   pull_request:
-    types: [opened, synchronize, closed]
+    types: [ opened, synchronize, closed ]
     paths:
       - 'python/docs/**'
       - 'python/lib/**'
@@ -36,7 +36,7 @@ jobs:
       - name: Install dependencies
         run: |
           cd python
-          pip install -e .[docs,development]
+          pip install -e .[docs-build]
 
       - name: Extract version
         id: version
@@ -91,8 +91,8 @@ jobs:
       - name: Install dependencies
         run: |
           cd python
-          pip install -e .[docs,development]
-          
+          pip install -e .[docs-build]
+
       - name: Fetch gh-pages branch
         run: git fetch origin gh-pages --depth=1
 
diff --git a/.github/workflows/python_ci.yaml b/.github/workflows/python_ci.yaml
index 2bb3579c7..1e5818dc5 100644
--- a/.github/workflows/python_ci.yaml
+++ b/.github/workflows/python_ci.yaml
@@ -30,7 +30,7 @@ jobs:
         id: install
         run: |
           python -m pip install --upgrade pip
-          pip install '.[development,data_review,openssl,tdms,rosbags,hdf5,sift-stream]'
+          pip install '.[dev-all]'
 
       - name: Lint
         run: |
@@ -48,6 +48,16 @@ jobs:
         run: |
           pyright lib
 
+      - name: Check Stubs Generation
+        working-directory: .
+        run: |
+          bash .githooks/pre-push-python/stubs.sh
+
+      - name: Check Extras Generation
+        working-directory: .
+        run: |
+          bash .githooks/pre-push-python/extras.sh
+
       - name: Pytest Unit Tests
         run: |
           pytest -m "not integration"
diff --git a/.github/workflows/python_release.yaml b/.github/workflows/python_release.yaml
index fad61f3d7..e37f65f80 100644
--- a/.github/workflows/python_release.yaml
+++ b/.github/workflows/python_release.yaml
@@ -17,13 +17,13 @@ jobs:
 
   publish-to-pypi:
     name: Upload release to PyPI
-    needs: [python-ci, build-offline-archives]
+    needs: [ python-ci, build-offline-archives ]
     runs-on: ubuntu-latest
     environment:
       name: pypi
       url: https://pypi.org/p/sift_py
     permissions:
-      id-token: write  
+      id-token: write
     steps:
       - name: Download distributions
         uses: actions/download-artifact@v4
@@ -38,7 +38,7 @@ jobs:
 
   create-github-release:
     name: Create GitHub Release
-    needs: [build-offline-archives]
+    needs: [ build-offline-archives ]
     runs-on: ubuntu-latest
     permissions:
       contents: write
@@ -110,7 +110,7 @@ jobs:
       - name: Install dependencies
         run: |
           cd python
-          pip install -e .[docs,development]
+          pip install -e .[docs-build]
 
       - name: Extract version and check if stable
         id: version
@@ -125,7 +125,7 @@ jobs:
             MINOR=${BASH_REMATCH[2]}
             SUFFIX=${BASH_REMATCH[3]}
             VERSION="v${MAJOR}.${MINOR}"
-            
+          
             # Check if this is a stable release (no suffix like -alpha, -beta, -rc)
             if [[ -z "$SUFFIX" ]]; then
               # Stable release - use 'latest' alias and make visible
diff --git a/python/pyproject.toml b/python/pyproject.toml
index a490f6699..4dbc5664b 100644
--- a/python/pyproject.toml
+++ b/python/pyproject.toml
@@ -1,3 +1,7 @@
+[build-system]
+requires = ["setuptools"]
+build-backend = "setuptools.build_meta"
+
 [project]
 name = "sift_stack_py"
 version = "0.9.1"
@@ -44,6 +48,144 @@ Repository = "https://github.com/sift-stack/sift/tree/main/python"
 Changelog = "https://github.com/sift-stack/sift/tree/main/python/CHANGELOG.md"
 
 [project.optional-dependencies]
+# AUTO GENERATED EXTRAS — EDIT [tool.sift.extras] ONLY
+all = [
+    'cffi~=1.14',
+    'h5py~=3.11',
+    'npTDMS~=1.9',
+    'polars~=1.8',
+    'pyOpenSSL<24.0.0',
+    'pyarrow>=17.0.0',
+    'rosbags~=0.0',
+    'sift-stream-bindings>=0.2.0-rc',
+    'types-pyOpenSSL<24.0.0',
+]
+build = [
+    'build==1.2.1',
+    'pdoc==14.5.0',
+]
+data-review = [
+    'pyarrow>=17.0.0',
+]
+dev = [
+    'grpcio-testing~=1.13',
+    'mypy==1.10.0',
+    'pyright==1.1.386',
+    'pytest-asyncio==0.23.7',
+    'pytest-benchmark==4.0.0',
+    'pytest-dotenv==0.5.2',
+    'pytest-mock==3.14.0',
+    'pytest==8.2.2',
+    'ruff~=0.12.10',
+    'tomlkit~=0.13.3',
+]
+dev-all = [
+    'build==1.2.1',
+    'cffi~=1.14',
+    'grpcio-testing~=1.13',
+    'h5py~=3.11',
+    'mypy==1.10.0',
+    'npTDMS~=1.9',
+    'pdoc==14.5.0',
+    'polars~=1.8',
+    'pyOpenSSL<24.0.0',
+    'pyarrow>=17.0.0',
+    'pyright==1.1.386',
+    'pytest-asyncio==0.23.7',
+    'pytest-benchmark==4.0.0',
+    'pytest-dotenv==0.5.2',
+    'pytest-mock==3.14.0',
+    'pytest==8.2.2',
+    'rosbags~=0.0',
+    'ruff~=0.12.10',
+    'sift-stream-bindings>=0.2.0-rc',
+    'tomlkit~=0.13.3',
+    'types-pyOpenSSL<24.0.0',
+]
+development = [
+    'grpcio-testing~=1.13',
+    'mypy==1.10.0',
+    'pyright==1.1.386',
+    'pytest-asyncio==0.23.7',
+    'pytest-benchmark==4.0.0',
+    'pytest-dotenv==0.5.2',
+    'pytest-mock==3.14.0',
+    'pytest==8.2.2',
+    'ruff~=0.12.10',
+    'tomlkit~=0.13.3',
+]
+docs = [
+    'griffe-pydantic',
+    'mike',
+    'mkdocs',
+    'mkdocs-api-autonav',
+    'mkdocs-include-markdown-plugin',
+    'mkdocs-jupyter',
+    'mkdocs-material',
+    'mkdocstrings[python]',
+]
+docs-build = [
+    'build==1.2.1',
+    'cffi~=1.14',
+    'griffe-pydantic',
+    'grpcio-testing~=1.13',
+    'h5py~=3.11',
+    'mike',
+    'mkdocs',
+    'mkdocs-api-autonav',
+    'mkdocs-include-markdown-plugin',
+    'mkdocs-jupyter',
+    'mkdocs-material',
+    'mkdocstrings[python]',
+    'mypy==1.10.0',
+    'npTDMS~=1.9',
+    'pdoc==14.5.0',
+    'polars~=1.8',
+    'pyOpenSSL<24.0.0',
+    'pyarrow>=17.0.0',
+    'pyright==1.1.386',
+    'pytest-asyncio==0.23.7',
+    'pytest-benchmark==4.0.0',
+    'pytest-dotenv==0.5.2',
+    'pytest-mock==3.14.0',
+    'pytest==8.2.2',
+    'rosbags~=0.0',
+    'ruff~=0.12.10',
+    'sift-stream-bindings>=0.2.0-rc',
+    'tomlkit~=0.13.3',
+    'types-pyOpenSSL<24.0.0',
+]
+file-imports = [
+    'h5py~=3.11',
+    'npTDMS~=1.9',
+    'polars~=1.8',
+    'rosbags~=0.0',
+]
+hdf5 = [
+    'h5py~=3.11',
+    'polars~=1.8',
+]
+openssl = [
+    'cffi~=1.14',
+    'pyOpenSSL<24.0.0',
+    'types-pyOpenSSL<24.0.0',
+]
+rosbags = [
+    'rosbags~=0.0',
+]
+sift-stream = [
+    'sift-stream-bindings>=0.2.0-rc',
+]
+sift-stream-bindings = [
+    'sift-stream-bindings>=0.2.0-rc',
+]
+tdms = [
+    'npTDMS~=1.9',
+]
+
+[tool.sift.extras]
+# Extras configurations defined here will be available in [project.optional-dependencies]
+
 # development
 development = [
     "grpcio-testing~=1.13",
@@ -55,6 +197,7 @@ development = [
     "pytest-mock==3.14.0",
     "pytest-dotenv==0.5.2",
     "ruff~=0.12.10",
+    "tomlkit~=0.13.3"
 ]
 build = ["pdoc==14.5.0", "build==1.2.1"]
 docs = ["mkdocs",
@@ -72,12 +215,21 @@ tdms = ["npTDMS~=1.9"]
 rosbags = ["rosbags~=0.0"]
 sift-stream = ["sift-stream-bindings>=0.2.0-rc"]
 hdf5 = ["h5py~=3.11", "polars~=1.8"]
-data_review = ["pyarrow>=17.0.0"]
-# Ensure any new user build extras are added to .github/workflows/python_build.yaml
+data-review = ["pyarrow>=17.0.0"]
 
-[build-system]
-requires = ["setuptools"]
-build-backend = "setuptools.build_meta"
+[tool.sift.extras.combine]
+# Combined extras configurations and aliases can be defined here
+
+# aliases
+dev = ["development"]
+sift-stream-bindings = ["sift-stream"]
+
+# combinations
+file-imports = ["tdms", "rosbags", "hdf5"]
+all = ["openssl", "sift-stream", "file-imports", "data-review"]
+
+dev-all = ["development", "all", "build"]
+docs-build = ["dev-all", "docs"] # Note python 3.9+
 
 [tool.mypy]
 python_version = "3.10" # Use the Python 3.10 type checker since we are using eval-type-backport and `from __future__ import annotations`
diff --git a/python/scripts/build_utils.py b/python/scripts/build_utils.py
index 43225ac8e..cfa085a25 100644
--- a/python/scripts/build_utils.py
+++ b/python/scripts/build_utils.py
@@ -104,7 +104,9 @@ def main():
 
     # Get all extras from the wheel
     extras = get_extras_from_wheel(str(wheel_file))
-    combinations = get_extra_combinations(extras, exclude=["development", "docs"])
+    combinations = get_extra_combinations(
+        extras, exclude=["development", "docs", "dev", "dev-all", "docs-build"]
+    )
 
     # Test base installation first
     test_install(
diff --git a/python/scripts/dev b/python/scripts/dev
index 7a95a5ced..6a610805b 100755
--- a/python/scripts/dev
+++ b/python/scripts/dev
@@ -20,6 +20,7 @@ Subcommands:
   pyright        Runs 'pyright lib' for type checking
   check          Runs all python linting checks
   gen-stubs      Generates pyi stubs for sift_client synchronous wrappers
+  gen-extras     Generates optional-dependencies in pyproject.toml
   mypy-stubs     Runs stubtest (mypy) on the generated pyi stubs
   pip-install    Install project dependencies
   test           Execute tests
@@ -34,7 +35,7 @@ EOT
 
 pip_install() {
   source venv/bin/activate
-  pip install '.[development,build,docs,openssl,tdms,rosbags,sift-stream,hdf5]'
+  pip install '.[all-dev]'
   pip install -e .
 }
 
@@ -119,6 +120,13 @@ mypy_stubs() {
   stubtest sift_client.resources.sync_stubs
 }
 
+gen_extras() {
+  source venv/bin/activate
+  cd scripts
+  python3 generate_extras.py
+  cd ..
+}
+
 shift "$((OPTIND - 1))"
 
 case "$1" in
@@ -168,6 +176,9 @@ case "$1" in
     gen-stubs)
         gen_stubs
         ;;
+    gen-extras)
+        gen_extras
+        ;;
     mypy-stubs)
         mypy_stubs
         ;;
diff --git a/python/scripts/generate_extras.py b/python/scripts/generate_extras.py
new file mode 100644
index 000000000..731765571
--- /dev/null
+++ b/python/scripts/generate_extras.py
@@ -0,0 +1,104 @@
+"""
+Generate [project.optional-dependencies] from [tool.sift.extras] configuration.
+
+This script reads the custom [tool.sift.extras] section in pyproject.toml and generates
+the standard [project.optional-dependencies] section automatically.
+
+Input sections:
+  - [tool.sift.extras]: Atomic extras with direct dependency lists
+  - [tool.sift.extras.combine]: Combined extras that reference other extras
+
+Output:
+  - [project.optional-dependencies]: Auto-generated, sorted extras with resolved dependencies
+
+The script:
+  1. Reads atomic extras (e.g., "dev", "openssl") from [tool.sift.extras]
+  2. Reads combined extras (e.g., "all" = ["openssl", "dev"]) from [tool.sift.extras.combine]
+  3. Recursively resolves all dependencies
+  4. Writes sorted, deduplicated lists to [project.optional-dependencies]
+  5. Preserves TOML formatting and comments using tomlkit
+"""
+
+import sys
+from pathlib import Path
+
+import tomlkit
+
+pyproject = Path("../pyproject.toml")
+if not pyproject.exists():
+    sys.exit(f"❌ No pyproject.toml found at {pyproject.resolve()}")
+
+# Parse preserving comments and formatting
+doc = tomlkit.parse(pyproject.read_text())
+
+try:
+    tool_sift = doc["tool"]["sift"]["extras"]
+except KeyError:
+    sys.exit("❌ No [tool.sift.extras] section found in pyproject.toml")
+
+# Split atomic and combined definitions
+combine_section = tool_sift.get("combine", {})
+atomic_extras = {k: v for k, v in tool_sift.items() if k != "combine"}
+
+
+def resolve(name, stack=None):
+    """
+    Recursively resolve an extra's dependencies.
+
+    Args:
+        name: The extra name to resolve (e.g., "dev-all")
+        stack: Internal tracking for cycle detection
+
+    Returns:
+        List of all dependency strings for this extra
+
+    Raises:
+        ValueError: If a cyclic dependency is detected
+        KeyError: If an unknown extra is referenced
+    """
+    if stack is None:
+        stack = []
+    if name in stack:
+        raise ValueError(f"Cyclic combine detected: {' -> '.join(stack + [name])}")
+    if name in atomic_extras:
+        return list(atomic_extras[name])
+    if name in combine_section:
+        deps = []
+        for sub in combine_section[name]:
+            deps.extend(resolve(sub, stack + [name]))
+        return deps
+    raise KeyError(f"Unknown group '{name}' referenced in combine")
+
+
+# Build final extras dictionary
+final_extras = {}
+for name in list(atomic_extras) + list(combine_section):
+    deps = resolve(name)
+    final_extras[name] = sorted(set(deps))
+
+# Inject into [project.optional-dependencies]
+project = doc.setdefault("project", tomlkit.table())
+
+# Create the optional-dependencies table
+opt_table = tomlkit.table()
+
+# Add a header comment BEFORE the section
+opt_table.trivia.indent = ""
+opt_table.trivia.comment = "\n# AUTO GENERATED EXTRAS — EDIT [tool.sift.extras] ONLY"
+
+# Write arrays in sorted order
+for name in sorted(final_extras):
+    deps = final_extras[name]
+    arr = tomlkit.array(deps)
+    arr.multiline(True)
+    arr.as_string()
+    opt_table[name] = arr
+
+
+# Assign back to project
+project["optional-dependencies"] = opt_table
+
+# Dump back to file
+pyproject.write_text(tomlkit.dumps(doc))
+
+print("Updated [project.optional-dependencies]")