diff --git a/tests/driver/driver.ts b/tests/driver/driver.ts
index f43f21636..478ca93b4 100644
--- a/tests/driver/driver.ts
+++ b/tests/driver/driver.ts
@@ -21,6 +21,8 @@ export interface SetupSettings {
   trunkVersion?: string;
 }
 
+export type CustomExecOptions = ExecOptions & { stdin?: string };
+
 const execFilePromise = util.promisify(execFile);
 
 const TEMP_SUBDIR = "tmp";
@@ -378,13 +380,41 @@ export abstract class GenericTrunkDriver {
    * Run a command inside the sandbox test repo.
    * @param bin command to run
    * @param args arguments to run
-   * @param execOptions
+   * @param execOptions options to pass the stdin to exec
    */
-  async run(bin: string, args: string[], execOptions?: ExecOptions) {
-    return await execFilePromise(bin, args, {
+  async run(bin: string, args: string[], execOptions?: CustomExecOptions) {
+    const exec = execFile(bin, args, {
       cwd: this.sandboxPath,
       env: executionEnv(this.sandboxPath ?? ""),
       ...execOptions,
     });
+    exec.stdin?.write(execOptions?.stdin ?? "");
+    exec.stdin?.end();
+
+    return await new Promise<{ stdout: string; stderr: string }>((resolve, reject) => {
+      let stdout = "";
+      let stderr = "";
+
+      exec.stdout?.on("data", (chunk: string) => {
+        stdout += chunk;
+      });
+
+      exec.stderr?.on("data", (chunk: string) => {
+        stderr += chunk;
+      });
+
+      exec.on("error", (err: any) => {
+        // trunk-ignore(eslint/@typescript-eslint/prefer-promise-reject-errors)
+        reject(err);
+      });
+      exec.on("exit", (code: number) => {
+        if (code === 0) {
+          resolve({ stdout, stderr });
+        } else {
+          // trunk-ignore(eslint/@typescript-eslint/prefer-promise-reject-errors)
+          reject({ error: new Error(`Process exited with code ${code}`), code, stdout, stderr });
+        }
+      });
+    });
   }
 }
diff --git a/tests/driver/tool_driver.ts b/tests/driver/tool_driver.ts
index 091e4d4fb..ff578b068 100644
--- a/tests/driver/tool_driver.ts
+++ b/tests/driver/tool_driver.ts
@@ -195,16 +195,17 @@ lint:
 
   /**** Execution methods ****/
 
-  async runTool(command: string[]): Promise<TrunkToolRunResult> {
+  async runTool(command: string[], stdin?: string): Promise<TrunkToolRunResult> {
     const tools_subdir = fs.existsSync(path.resolve(this.sandboxPath ?? "", ".trunk/dev-tools"))
       ? "dev-tools"
       : "tools";
     try {
       if (process.platform == "win32") {
-        const { stdout, stderr } = await this.run("powershell", [
-          `.trunk/${tools_subdir}/${command[0]}.bat`,
-          ...command.slice(1),
-        ]);
+        const { stdout, stderr } = await this.run(
+          "powershell",
+          [`.trunk/${tools_subdir}/${command[0]}.bat`, ...command.slice(1)],
+          { stdin },
+        );
         return {
           exitCode: 0,
           stdout,
@@ -215,6 +216,7 @@ lint:
       const { stdout, stderr } = await this.run(
         `.trunk/${tools_subdir}/${command[0]}`,
         command.slice(1),
+        { stdin },
       );
       return {
         exitCode: 0,
diff --git a/tests/index.ts b/tests/index.ts
index e15dfe4e4..b08deac33 100644
--- a/tests/index.ts
+++ b/tests/index.ts
@@ -267,6 +267,7 @@ interface ToolTestConfig {
   expectedOut?: string;
   expectedErr?: string;
   expectedExitCode?: number;
+  stdin?: string;
 }
 
 export const makeToolTestConfig = ({
@@ -274,11 +275,13 @@ export const makeToolTestConfig = ({
   expectedOut = "",
   expectedErr = "",
   expectedExitCode = 0,
+  stdin = "",
 }: ToolTestConfig) => ({
   command,
   expectedOut,
   expectedErr,
   expectedExitCode,
+  stdin,
 });
 
 export const toolTest = ({
@@ -298,9 +301,9 @@ export const toolTest = ({
 }) => {
   describe(`Testing tool ${toolName}`, () => {
     const driver = setupTrunkToolDriver(dirName, {}, toolName, toolVersion, preCheck);
-    testConfigs.forEach(({ command, expectedOut, expectedErr, expectedExitCode }) => {
+    testConfigs.forEach(({ command, expectedOut, expectedErr, expectedExitCode, stdin }) => {
       conditionalTest(skipTestIf(toolVersion), command.join(" "), async () => {
-        const { stdout, stderr, exitCode } = await driver.runTool(command);
+        const { stdout, stderr, exitCode } = await driver.runTool(command, stdin);
         expect(stdout).toContain(expectedOut);
         expect(stderr).toContain(expectedErr);
         expect(exitCode).toEqual(expectedExitCode);
diff --git a/tools/diff-so-fancy/diff_so_fancy.test.ts b/tools/diff-so-fancy/diff_so_fancy.test.ts
index 34f2d8caa..457174c53 100644
--- a/tools/diff-so-fancy/diff_so_fancy.test.ts
+++ b/tools/diff-so-fancy/diff_so_fancy.test.ts
@@ -1,7 +1,34 @@
-import { toolInstallTest } from "tests";
+import { makeToolTestConfig, toolTest } from "tests";
 
-// TODO(Tyler): tool def is missing healthcheck
-toolInstallTest({
+const sampleDiff = `diff --git a/.trunk/trunk.yaml b/.trunk/trunk.yaml
+index dc4f1f8..fb8fe54 100644
+--- a/.trunk/trunk.yaml
++++ b/.trunk/trunk.yaml
+@@ -13,3 +13,6 @@ lint:
+         - node_modules/**
+         - .trunk/configs/**
+         - .gitattributes
++tools:
++  enabled:
++    - diff-so-fancy@1.4.3`;
+
+let exitCode = 25;
+if (process.platform === "darwin") {
+  exitCode = 102;
+} else if (process.platform === "win32") {
+  exitCode = 0;
+}
+// diff-so-fancy returns a nonzero exit code for its version command, so we have to
+// use the custom test constructor.
+toolTest({
   toolName: "diff-so-fancy",
   toolVersion: "1.4.3",
+  testConfigs: [
+    makeToolTestConfig({
+      command: ["diff-so-fancy"],
+      expectedExitCode: exitCode,
+      expectedOut: "modified:",
+      stdin: sampleDiff,
+    }),
+  ],
 });
diff --git a/tools/difft/difft.test.ts b/tools/difft/difft.test.ts
index fdbd2dec8..40e310e56 100644
--- a/tools/difft/difft.test.ts
+++ b/tools/difft/difft.test.ts
@@ -1,6 +1,5 @@
 import { toolInstallTest } from "tests";
 
-// TODO(Tyler): tool def is missing healthcheck
 toolInstallTest({
   toolName: "difft",
   toolVersion: "0.56.1",
diff --git a/tools/difft/plugin.yaml b/tools/difft/plugin.yaml
index eb0eb016f..ad295dc69 100644
--- a/tools/difft/plugin.yaml
+++ b/tools/difft/plugin.yaml
@@ -20,3 +20,6 @@ tools:
       download: difft
       known_good_version: 0.56.1
       shims: [difft]
+      health_checks:
+        - command: difft --version
+          parse_regex: Difftastic ${semver}
diff --git a/tools/gk/gk.test.ts b/tools/gk/gk.test.ts
index 67b9a1896..347cfd8a9 100644
--- a/tools/gk/gk.test.ts
+++ b/tools/gk/gk.test.ts
@@ -1,7 +1,8 @@
-import { toolInstallTest } from "tests";
+import { makeToolTestConfig, toolTest } from "tests";
 
-// TODO(Tyler): tool def is missing healthcheck
-toolInstallTest({
+// No version command for gk
+toolTest({
   toolName: "gk",
   toolVersion: "1.2.2",
+  testConfigs: [makeToolTestConfig({ command: ["gk", "-h"], expectedErr: "Usage" })],
 });
diff --git a/tools/goreleaser/goreleaser.test.ts b/tools/goreleaser/goreleaser.test.ts
index c9781a483..6e6b8e8f8 100644
--- a/tools/goreleaser/goreleaser.test.ts
+++ b/tools/goreleaser/goreleaser.test.ts
@@ -1,11 +1,13 @@
-import { toolInstallTest } from "tests";
+import { makeToolTestConfig, toolTest } from "tests";
 import { osTimeoutMultiplier } from "tests/utils";
 
 // This install is quite slow on some Linux machines.
 jest.setTimeout(600000 * osTimeoutMultiplier);
 
-// TODO(Tyler): tool def is missing healthcheck
-toolInstallTest({
+toolTest({
   toolName: "goreleaser",
   toolVersion: "1.25.1",
+  testConfigs: [
+    makeToolTestConfig({ command: ["goreleaser", "--version"], expectedOut: "goreleaser" }),
+  ],
 });
diff --git a/tools/tsc/plugin.yaml b/tools/tsc/plugin.yaml
index cce3dd100..1935cf23a 100644
--- a/tools/tsc/plugin.yaml
+++ b/tools/tsc/plugin.yaml
@@ -6,3 +6,6 @@ tools:
       package: typescript
       known_good_version: 5.2.2
       shims: [tsc]
+      health_checks:
+        - command: tsc --version
+          parse_regex: Version ${semver}
diff --git a/tools/tsc/tsc.test.ts b/tools/tsc/tsc.test.ts
index 9f1c81716..f156d5040 100644
--- a/tools/tsc/tsc.test.ts
+++ b/tools/tsc/tsc.test.ts
@@ -1,7 +1,6 @@
 import { toolInstallTest } from "tests";
 import { skipOS } from "tests/utils";
 
-// TODO(Tyler): tool def is missing healthcheck
 toolInstallTest({
   toolName: "tsc",
   toolVersion: "5.2.2",
diff --git a/tools/yq/plugin.yaml b/tools/yq/plugin.yaml
index 79c05943c..f3519367a 100644
--- a/tools/yq/plugin.yaml
+++ b/tools/yq/plugin.yaml
@@ -8,16 +8,19 @@ downloads:
         cpu:
           x86_64: 386
           arm_64: arm64
-        url: https://github.com/mikefarah/yq/releases/download/v${version}/yq_${os}_${cpu}.tar.gz
+        url: https://github.com/mikefarah/yq/releases/download/v${version}/yq_${os}_${cpu}
       - os:
           windows: windows
         cpu:
           x86_64: 386
           arm_64: arm64
-        url: https://github.com/mikefarah/yq/releases/download/v${version}/yq_${os}_${cpu}.zip
+        url: https://github.com/mikefarah/yq/releases/download/v${version}/yq_${os}_${cpu}.exe
 tools:
   definitions:
     - name: yq
       download: yq
-      known_good_version: 4.40.5
+      known_good_version: 4.44.1
       shims: [yq]
+      health_checks:
+        - command: yq --version
+          parse_regex: version v${semver}
diff --git a/tools/yq/yq.test.ts b/tools/yq/yq.test.ts
index f2318f455..c256e557a 100644
--- a/tools/yq/yq.test.ts
+++ b/tools/yq/yq.test.ts
@@ -1,7 +1,7 @@
 import { toolInstallTest } from "tests";
 
-// TODO(Tyler): tool def is missing healthcheck
+// The binary name varies by platform so we can't roll this into a health_check as-is.
 toolInstallTest({
   toolName: "yq",
-  toolVersion: "4.40.5",
+  toolVersion: "4.44.1",
 });