diff --git a/bin/generate_tests b/bin/generate_tests
new file mode 100755
index 00000000..56edc7ca
--- /dev/null
+++ b/bin/generate_tests
@@ -0,0 +1,200 @@
+#!/usr/bin/env python3
+
+"""Test generator v1."""
+
+import argparse
+import datetime
+import json
+import os
+import pathlib
+import re
+import subprocess
+import sys
+import textwrap
+import tomllib
+
+import jinja2
+
+
+def problem_spec_dir() -> pathlib.Path:
+    """Detect and return the problem specs."""
+    cache_dir = os.getenv("XDG_CACHE_HOME", os.getenv("HOME") + "/.cache")
+    specs = pathlib.Path(cache_dir) / "exercism/configlet/problem-specifications"
+    if specs.exists():
+        return specs
+    cur = pathlib.Path(os.getcwd())
+    for i in cur.parents:
+        if i.name == "problem-specifications":
+            return i
+    raise LookupError("Could not find problem specs")
+
+
+def flatten_cases(cases: list[dict]) -> list[tuple[list[str], dict]]:
+    """Recursive flatten test cases, returning individual cases with parent descriptions."""
+    for case_or_group in cases:
+        if "cases" in case_or_group:
+            for groups, child_case in flatten_cases(case_or_group["cases"]):
+                yield ([case_or_group["description"]] + groups, child_case)
+        else:
+            yield ([], case_or_group)
+
+
+def get_cases(specs: pathlib.Path, exercise: pathlib.Path) -> list[dict]:
+    """Return flattened, filtered cases with additional metadata attached."""
+    canonical_path = specs / "exercises" / exercise.name / "canonical-data.json"
+    with open(canonical_path, "r", encoding="utf-8") as f:
+        canonical = json.load(f)
+    with open(exercise / ".meta" / "tests.toml", "rb") as f:
+        tests = tomllib.load(f)
+
+    reimplemented = {
+        test["reimplements"]
+        for test in tests.values()
+        if test.get("include", True) and "reimplements" in test
+    }
+    cases = []
+    for groups, case in flatten_cases(canonical["cases"]):
+        # Filter out test cases with include=false or not listed.
+        if case["uuid"] not in tests or case["uuid"] in reimplemented:
+            continue
+        if not tests[case["uuid"]].get("include", True):
+            continue
+        # Add metadata.
+        case["descriptions"] = groups + [case["description"]]
+        case["expect_error"] = isinstance(case["expected"], dict) and "error" in case["expected"]
+        if case["expect_error"]:
+            case["expect_error_msg"] = case["expected"]["error"]
+        cases.append(case)
+    return cases
+
+
+def filter_tojson(data, separators=(',', ':'), indent=None) -> str:
+    """Filter `tojson` that JSON encodes a string with flexible settings."""
+    return json.dumps(data, separators=separators, indent=indent)
+
+
+def jinja_env(exercise: pathlib.Path) -> jinja2.Environment:
+    """Return a configured Jinja env with filters added."""
+    env = jinja2.Environment(loader=jinja2.FileSystemLoader(exercise / ".meta"))
+    env.filters["camel_to_snake"] = lambda x: re.sub(r"([a-z])([A-Z])", (lambda m: f"{m.group(1)}_{m.group(2).lower()}"), x)
+    # JSON formatting, default to compact form (`jq -c`).
+    env.filters["tojson"] = filter_tojson
+    # String escaping, Tcl style:
+    # first express as a JSON string (this exposes all whitespace characters, and adds quotes)
+    # then protect Tcl special characters
+    env.filters["tclstring"] = lambda x: re.sub(r'([\[\$])', r'\\\1', filter_tojson(x))
+    return env
+
+
+def bool_to_str(obj):
+    """Convert boolean values to strings."""
+    if isinstance(obj, dict):
+        return {key: bool_to_str(val) for key, val in obj.items()}
+    if isinstance(obj, list):
+        return [bool_to_str(val) for val in obj]
+    if obj is True:
+        return "true"
+    if obj is False:
+        return "false"
+    return obj
+
+
+def generate(specs: pathlib.Path, exercise: pathlib.Path) -> None:
+    """Generate and write test file for a given spec and exercise."""
+    cases = get_cases(specs, exercise)
+    for case in cases:
+        case["expected"] = bool_to_str(case["expected"])
+
+    timestamp = datetime.datetime.now(tz=datetime.UTC).replace(microsecond=0).isoformat()
+    exercise_config = json.loads((exercise / ".meta/config.json").read_text())
+
+    header = textwrap.dedent(f"""\
+        #!/usr/bin/env tclsh
+        # generated on {timestamp}
+        package require tcltest
+        namespace import ::tcltest::*
+        source testHelpers.tcl
+
+        # Uncomment next line to view test durations.
+        #configure -verbose {{body error usec}}
+
+        ############################################################
+        source "{exercise_config["files"]["solution"][0]}"
+        """
+    ).strip()
+    data = {
+        "cases": list(enumerate(cases)),
+        "header": header,
+        "footer": "\ncleanupTests",
+        "slug": exercise.name,
+    }
+
+    # Render the template.
+    try:
+        template = jinja_env(exercise).get_template("template.j2")
+        out = template.render(data)
+    except jinja2.exceptions.TemplateAssertionError as e:
+        e.add_note(f"Error rendering template for {exercise.name}")
+        raise
+
+    # Check for changes or the lack thereof.
+    test_file = exercise / json.loads((exercise / ".meta/config.json").read_text())["files"]["test"][0]
+    if test_file.exists():
+        old_content = [i for i in test_file.read_text().strip().splitlines() if "generated on" not in i]
+        new_content = [i for i in out.splitlines() if "generated on" not in i]
+        if old_content == new_content:
+            return
+
+    # Write the test file.
+    test_file.write_text(out + "\n")
+
+
+def argparser() -> argparse.ArgumentParser:
+    parser = argparse.ArgumentParser()
+    parser.add_argument(
+        "--no-pull",
+        action="store_false",
+        dest="pull",
+        help="Do not run `git pull` on the problem specs repo",
+    )
+    parser.add_argument(
+        "exercises",
+        nargs="*",
+        help="exercises to generate tests; if none supplied, generate all"
+    )
+    return parser
+
+
+def main():
+    """Main entrypoint."""
+    specs = problem_spec_dir()
+    args = argparser().parse_args()
+    if args.pull:
+        subprocess.check_call(["git", "pull"], cwd=specs)
+    exercises = args.exercises
+    # Generate all exercises with templates if none are specified as args.
+    if not exercises:
+        exercises = [
+            i.parent.parent
+            for i in pathlib.Path("exercises/practice").glob("*/.meta/template.j2")
+        ]
+    else:
+        # Turn strings to paths and make them relative to the practice exercises.
+        out = []
+        practice = pathlib.Path("exercises/practice")
+        for exercise in exercises:
+            path = pathlib.Path(exercise)
+            if not path.is_relative_to(practice):
+                path = practice / path
+            out.append(path)
+        exercises = out
+
+    for exercise in exercises:
+        exercise_path = pathlib.Path(exercise)
+        if not exercise_path.exists():
+            raise ValueError(f"Exercise {exercise_path} does not exist")
+        generate(specs, exercise_path)
+
+
+if __name__ == "__main__":
+    main()
diff --git a/exercises/practice/bob/.meta/template.j2 b/exercises/practice/bob/.meta/template.j2
new file mode 100644
index 00000000..0f0b5f4e
--- /dev/null
+++ b/exercises/practice/bob/.meta/template.j2
@@ -0,0 +1,13 @@
+{{ header }}
+
+{% for idx, case in cases -%}
+{%   if idx > 0 -%}
+skip {{slug}}-{{idx + 1}}
+{%   endif -%}
+test {{slug}}-{{idx + 1}} "{{ case["description"] }}" -body {
+    heyBob {{ case["input"]["heyBob"] | tclstring }}
+} -returnCodes ok -result "{{ case["expected"] }}"
+
+{% endfor -%}
+
+{{footer}}
diff --git a/exercises/practice/bob/.meta/tests.toml b/exercises/practice/bob/.meta/tests.toml
index 5299e289..c6a46496 100644
--- a/exercises/practice/bob/.meta/tests.toml
+++ b/exercises/practice/bob/.meta/tests.toml
@@ -9,17 +9,20 @@
 # As user-added comments (using the # character) will be removed when this file
 # is regenerated, comments can be added via a `comment` key.
 
-[e162fead-606f-437a-a166-d051915cea8e]
-description = "stating something"
+[8a2e771d-d6f1-4e3f-b6c6-b41495556e37]
+description = "asking a question"
 
 [73a966dc-8017-47d6-bb32-cf07d1a5fcd9]
 description = "shouting"
 
-[d6c98afd-df35-4806-b55e-2c457c3ab748]
-description = "shouting gibberish"
+[a5193c61-4a92-4f68-93e2-f554eb385ec6]
+description = "forceful question"
 
-[8a2e771d-d6f1-4e3f-b6c6-b41495556e37]
-description = "asking a question"
+[bc39f7c6-f543-41be-9a43-fd1c2f753fc0]
+description = "silence"
+
+[e162fead-606f-437a-a166-d051915cea8e]
+description = "stating something"
 
 [81080c62-4e4d-4066-b30a-48d8d76920d9]
 description = "asking a numeric question"
@@ -27,23 +30,34 @@ description = "asking a numeric question"
 [2a02716d-685b-4e2e-a804-2adaf281c01e]
 description = "asking gibberish"
 
-[c02f9179-ab16-4aa7-a8dc-940145c385f7]
-description = "talking forcefully"
+[bb0011c5-cd52-4a5b-8bfb-a87b6283b0e2]
+description = "question with no letters"
 
-[153c0e25-9bb5-4ec5-966e-598463658bcd]
-description = "using acronyms in regular speech"
+[9bfc677d-ea3a-45f2-be44-35bc8fa3753e]
+description = "non-letters with question"
 
-[a5193c61-4a92-4f68-93e2-f554eb385ec6]
-description = "forceful question"
+[8608c508-f7de-4b17-985b-811878b3cf45]
+description = "prattling on"
 
-[a20e0c54-2224-4dde-8b10-bd2cdd4f61bc]
-description = "shouting numbers"
+[05b304d6-f83b-46e7-81e0-4cd3ca647900]
+description = "ending with whitespace"
 
-[f7bc4b92-bdff-421e-a238-ae97f230ccac]
-description = "no letters"
+[66953780-165b-4e7e-8ce3-4bcb80b6385a]
+description = "multiple line question"
+include = false
 
-[bb0011c5-cd52-4a5b-8bfb-a87b6283b0e2]
-description = "question with no letters"
+[2c7278ac-f955-4eb4-bf8f-e33eb4116a15]
+description = "multiple line question"
+reimplements = "66953780-165b-4e7e-8ce3-4bcb80b6385a"
+
+[d6c98afd-df35-4806-b55e-2c457c3ab748]
+description = "shouting gibberish"
+
+[3c954328-86fb-4c71-8961-e18d6a5e2517]
+description = "shouting a statement containing a question mark"
+
+[a20e0c54-2224-4dde-8b10-bd2cdd4f61bc]
+description = "shouting numbers"
 
 [496143c8-1c31-4c01-8a08-88427af85c66]
 description = "shouting with special characters"
@@ -51,40 +65,29 @@ description = "shouting with special characters"
 [e6793c1c-43bd-4b8d-bc11-499aea73925f]
 description = "shouting with no exclamation mark"
 
-[aa8097cc-c548-4951-8856-14a404dd236a]
-description = "statement containing question mark"
-
-[9bfc677d-ea3a-45f2-be44-35bc8fa3753e]
-description = "non-letters with question"
-
-[8608c508-f7de-4b17-985b-811878b3cf45]
-description = "prattling on"
-
-[bc39f7c6-f543-41be-9a43-fd1c2f753fc0]
-description = "silence"
-
 [d6c47565-372b-4b09-b1dd-c40552b8378b]
 description = "prolonged silence"
 
 [4428f28d-4100-4d85-a902-e5a78cb0ecd3]
 description = "alternate silence"
 
-[66953780-165b-4e7e-8ce3-4bcb80b6385a]
-description = "multiple line question"
-include = false
+[72bd5ad3-9b2f-4931-a988-dce1f5771de2]
+description = "other whitespace"
 
-[5371ef75-d9ea-4103-bcfa-2da973ddec1b]
-description = "starting with whitespace"
+[c02f9179-ab16-4aa7-a8dc-940145c385f7]
+description = "talking forcefully"
 
-[05b304d6-f83b-46e7-81e0-4cd3ca647900]
-description = "ending with whitespace"
+[153c0e25-9bb5-4ec5-966e-598463658bcd]
+description = "using acronyms in regular speech"
 
-[72bd5ad3-9b2f-4931-a988-dce1f5771de2]
-description = "other whitespace"
+[f7bc4b92-bdff-421e-a238-ae97f230ccac]
+description = "no letters"
+
+[aa8097cc-c548-4951-8856-14a404dd236a]
+description = "statement containing question mark"
+
+[5371ef75-d9ea-4103-bcfa-2da973ddec1b]
+description = "starting with whitespace"
 
 [12983553-8601-46a8-92fa-fcaa3bc4a2a0]
 description = "non-question ending with whitespace"
-
-[2c7278ac-f955-4eb4-bf8f-e33eb4116a15]
-description = "multiple line question"
-reimplements = "66953780-165b-4e7e-8ce3-4bcb80b6385a"
diff --git a/exercises/practice/bob/bob.test b/exercises/practice/bob/bob.test
index c4f1c9f0..adb5855a 100644
--- a/exercises/practice/bob/bob.test
+++ b/exercises/practice/bob/bob.test
@@ -1,133 +1,143 @@
 #!/usr/bin/env tclsh
+# generated on 2026-07-15T19:37:55+00:00
 package require tcltest
 namespace import ::tcltest::*
 source testHelpers.tcl
 
+# Uncomment next line to view test durations.
+#configure -verbose {body error usec}
+
 ############################################################
 source "bob.tcl"
 
-test bob-1  "stating something" -body {
-    heyBob "Tom-ay-to, tom-aaaah-to."
-} -returnCodes ok -result "Whatever."
+test bob-1 "asking a question" -body {
+    heyBob "Does this cryogenic chamber make me look fat?"
+} -returnCodes ok -result "Sure."
 
 skip bob-2
-test bob-2  "shouting" -body {
+test bob-2 "shouting" -body {
     heyBob "WATCH OUT!"
 } -returnCodes ok -result "Whoa, chill out!"
 
 skip bob-3
-test bob-3  "shouting gibberish" -body {
-    heyBob "FCECDFCAAB"
-} -returnCodes ok -result "Whoa, chill out!"
+test bob-3 "forceful question" -body {
+    heyBob "WHAT'S GOING ON?"
+} -returnCodes ok -result "Calm down, I know what I'm doing!"
 
 skip bob-4
-test bob-4  "asking a question" -body {
-    heyBob "Does this cryogenic chamber make me look fat?"
-} -returnCodes ok -result "Sure."
+test bob-4 "silence" -body {
+    heyBob ""
+} -returnCodes ok -result "Fine. Be that way!"
 
 skip bob-5
-test bob-5  "asking a numeric question" -body {
-    heyBob "You are, what, like 15?"
-} -returnCodes ok -result "Sure."
+test bob-5 "stating something" -body {
+    heyBob "Tom-ay-to, tom-aaaah-to."
+} -returnCodes ok -result "Whatever."
 
 skip bob-6
-test bob-6  "asking gibberish" -body {
-    heyBob "fffbbcbeab?"
+test bob-6 "asking a numeric question" -body {
+    heyBob "You are, what, like 15?"
 } -returnCodes ok -result "Sure."
 
 skip bob-7
-test bob-7  "talking forcefully" -body {
-    heyBob "Hi there!"
-} -returnCodes ok -result "Whatever."
+test bob-7 "asking gibberish" -body {
+    heyBob "fffbbcbeab?"
+} -returnCodes ok -result "Sure."
 
 skip bob-8
-test bob-8  "using acronyms in regular speech" -body {
-    heyBob "It's OK if you don't want to go work for NASA."
-} -returnCodes ok -result "Whatever."
+test bob-8 "question with no letters" -body {
+    heyBob "4?"
+} -returnCodes ok -result "Sure."
 
 skip bob-9
-test bob-9  "forceful question" -body {
-    heyBob "WHAT'S GOING ON?"
-} -returnCodes ok -result "Calm down, I know what I'm doing!"
+test bob-9 "non-letters with question" -body {
+    heyBob ":) ?"
+} -returnCodes ok -result "Sure."
 
 skip bob-10
-test bob-10 "shouting numbers" -body {
-    heyBob "1, 2, 3 GO!"
-} -returnCodes ok -result "Whoa, chill out!"
+test bob-10 "prattling on" -body {
+    heyBob "Wait! Hang on. Are you going to be OK?"
+} -returnCodes ok -result "Sure."
 
 skip bob-11
-test bob-11 "no letters" -body {
-    heyBob "1, 2, 3"
-} -returnCodes ok -result "Whatever."
+test bob-11 "ending with whitespace" -body {
+    heyBob "Okay if like my  spacebar  quite a bit?   "
+} -returnCodes ok -result "Sure."
 
 skip bob-12
-test bob-12 "question with no letters" -body {
-    heyBob "4?"
+test bob-12 "multiple line question" -body {
+    heyBob "\nDoes this cryogenic chamber make\n me look fat?"
 } -returnCodes ok -result "Sure."
 
 skip bob-13
-test bob-13 "shouting with special characters" -body {
-    heyBob "ZOMG THE %^*@#\$(*^ ZOMBIES ARE COMING!!11!!1!"
+test bob-13 "shouting gibberish" -body {
+    heyBob "FCECDFCAAB"
 } -returnCodes ok -result "Whoa, chill out!"
 
 skip bob-14
-test bob-14 "shouting with no exclamation mark" -body {
-    heyBob "I HATE THE DENTIST"
+test bob-14 "shouting a statement containing a question mark" -body {
+    heyBob "DO LIONS EAT PEOPLE? AHHHHH."
 } -returnCodes ok -result "Whoa, chill out!"
 
 skip bob-15
-test bob-15 "statement containing question mark" -body {
-    heyBob "Ending with ? means a question."
-} -returnCodes ok -result "Whatever."
+test bob-15 "shouting numbers" -body {
+    heyBob "1, 2, 3 GO!"
+} -returnCodes ok -result "Whoa, chill out!"
 
 skip bob-16
-test bob-16 "non-letters with question" -body {
-    heyBob ":) ?"
-} -returnCodes ok -result "Sure."
+test bob-16 "shouting with special characters" -body {
+    heyBob "ZOMG THE %^*@#\$(*^ ZOMBIES ARE COMING!!11!!1!"
+} -returnCodes ok -result "Whoa, chill out!"
 
 skip bob-17
-test bob-17 "prattling on" -body {
-    heyBob "Wait! Hang on. Are you going to be OK?"
-} -returnCodes ok -result "Sure."
+test bob-17 "shouting with no exclamation mark" -body {
+    heyBob "I HATE THE DENTIST"
+} -returnCodes ok -result "Whoa, chill out!"
 
 skip bob-18
-test bob-18 "silence" -body {
-    heyBob ""
+test bob-18 "prolonged silence" -body {
+    heyBob "          "
 } -returnCodes ok -result "Fine. Be that way!"
 
 skip bob-19
-test bob-19 "prolonged silence" -body {
-    heyBob "          "
+test bob-19 "alternate silence" -body {
+    heyBob "\t\t\t\t\t\t\t\t\t\t"
 } -returnCodes ok -result "Fine. Be that way!"
 
 skip bob-20
-test bob-20 "alternate silence" -body {
-    heyBob "\t\t\t\t\t\t\t\t\t\t"
+test bob-20 "other whitespace" -body {
+    heyBob "\n\r \t"
 } -returnCodes ok -result "Fine. Be that way!"
 
 skip bob-21
-test bob-21 "multiple line question" -body {
-    heyBob "\nDoes this cryogenic chamber make me look fat?"
-} -returnCodes ok -result "Sure."
+test bob-21 "talking forcefully" -body {
+    heyBob "Hi there!"
+} -returnCodes ok -result "Whatever."
 
 skip bob-22
-test bob-22 "starting with whitespace" -body {
-    heyBob "         hmmmmmmm..."
+test bob-22 "using acronyms in regular speech" -body {
+    heyBob "It's OK if you don't want to go work for NASA."
 } -returnCodes ok -result "Whatever."
 
 skip bob-23
-test bob-23 "ending with whitespace" -body {
-    heyBob "Okay if like my  spacebar  quite a bit?   "
-} -returnCodes ok -result "Sure."
+test bob-23 "no letters" -body {
+    heyBob "1, 2, 3"
+} -returnCodes ok -result "Whatever."
 
 skip bob-24
-test bob-24 "other whitespace" -body {
-    heyBob "\n\r \t"
-} -returnCodes ok -result "Fine. Be that way!"
+test bob-24 "statement containing question mark" -body {
+    heyBob "Ending with ? means a question."
+} -returnCodes ok -result "Whatever."
 
 skip bob-25
-test bob-25 "non-question ending with whitespace" -body {
+test bob-25 "starting with whitespace" -body {
+    heyBob "         hmmmmmmm..."
+} -returnCodes ok -result "Whatever."
+
+skip bob-26
+test bob-26 "non-question ending with whitespace" -body {
     heyBob "This is a statement ending with whitespace      "
 } -returnCodes ok -result "Whatever."
 
+
 cleanupTests