diff --git a/packages/cdk-assets/lib/private/docker.ts b/packages/cdk-assets/lib/private/docker.ts
index 7cca00a2d0cbd..509e15cbed22f 100644
--- a/packages/cdk-assets/lib/private/docker.ts
+++ b/packages/cdk-assets/lib/private/docker.ts
@@ -2,7 +2,7 @@ import * as fs from 'fs';
 import * as os from 'os';
 import * as path from 'path';
 import { cdkCredentialsConfig, obtainEcrCredentials } from './docker-credentials';
-import { Logger, shell, ShellOptions } from './shell';
+import { Logger, shell, ShellOptions, ProcessFailedError } from './shell';
 import { createCriticalSection } from './util';
 
 interface BuildOptions {
@@ -31,6 +31,11 @@ export interface DockerDomainCredentials {
   readonly ecrRepository?: string;
 }
 
+enum InspectImageErrorCode {
+  Docker = 1,
+  Podman = 125
+}
+
 export class Docker {
 
   private configDir: string | undefined = undefined;
@@ -46,8 +51,31 @@ export class Docker {
       await this.execute(['inspect', tag], { quiet: true });
       return true;
     } catch (e) {
-      if (e.code !== 'PROCESS_FAILED' || e.exitCode !== 1) { throw e; }
-      return false;
+      const error: ProcessFailedError = e;
+
+      /**
+       * The only error we expect to be thrown will have this property and value.
+       * If it doesn't, it's unrecognized so re-throw it.
+       */
+      if (error.code !== 'PROCESS_FAILED') {
+        throw error;
+      }
+
+      /**
+       * If we know the shell command above returned an error, check to see
+       * if the exit code is one we know to actually mean that the image doesn't
+       * exist.
+       */
+      switch (error.exitCode) {
+        case InspectImageErrorCode.Docker:
+        case InspectImageErrorCode.Podman:
+          // Docker and Podman will return this exit code when an image doesn't exist, return false
+          // context: https://github.com/aws/aws-cdk/issues/16209
+          return false;
+        default:
+          // This is an error but it's not an exit code we recognize, throw.
+          throw error;
+      }
     }
   }
 
diff --git a/packages/cdk-assets/lib/private/shell.ts b/packages/cdk-assets/lib/private/shell.ts
index 46eb7c6c571e1..ba7837f49810e 100644
--- a/packages/cdk-assets/lib/private/shell.ts
+++ b/packages/cdk-assets/lib/private/shell.ts
@@ -61,6 +61,8 @@ export async function shell(command: string[], options: ShellOptions = {}): Prom
   });
 }
 
+export type ProcessFailedError = ProcessFailed
+
 class ProcessFailed extends Error {
   public readonly code = 'PROCESS_FAILED';
 
diff --git a/packages/cdk-assets/test/private/docker.test.ts b/packages/cdk-assets/test/private/docker.test.ts
new file mode 100644
index 0000000000000..40c37ca35f271
--- /dev/null
+++ b/packages/cdk-assets/test/private/docker.test.ts
@@ -0,0 +1,94 @@
+import { Docker } from '../../lib/private/docker';
+import { ShellOptions, ProcessFailedError } from '../../lib/private/shell';
+
+type ShellExecuteMock = jest.SpyInstance<ReturnType<Docker['execute']>, Parameters<Docker['execute']>>;
+
+describe('Docker', () => {
+  describe('exists', () => {
+    let docker: Docker;
+
+    const makeShellExecuteMock = (
+      fn: (params: string[]) => void,
+    ): ShellExecuteMock =>
+      jest.spyOn<{ execute: Docker['execute'] }, 'execute'>(Docker.prototype as any, 'execute').mockImplementation(
+        async (params: string[], _options?: ShellOptions) => fn(params),
+      );
+
+    afterEach(() => {
+      jest.restoreAllMocks();
+    });
+
+    beforeEach(() => {
+      docker = new Docker();
+    });
+
+    test('returns true when image inspect command does not throw', async () => {
+      const spy = makeShellExecuteMock(() => undefined);
+
+      const imageExists = await docker.exists('foo');
+
+      expect(imageExists).toBe(true);
+      expect(spy.mock.calls[0][0]).toEqual(['inspect', 'foo']);
+    });
+
+    test('throws when an arbitrary error is caught', async () => {
+      makeShellExecuteMock(() => {
+        throw new Error();
+      });
+
+      await expect(docker.exists('foo')).rejects.toThrow();
+    });
+
+    test('throws when the error is a shell failure but the exit code is unrecognized', async () => {
+      makeShellExecuteMock(() => {
+        throw new (class extends Error implements ProcessFailedError {
+          public readonly code = 'PROCESS_FAILED'
+          public readonly exitCode = 47
+          public readonly signal = null
+
+          constructor() {
+            super('foo');
+          }
+        });
+      });
+
+      await expect(docker.exists('foo')).rejects.toThrow();
+    });
+
+    test('returns false when the error is a shell failure and the exit code is 1 (Docker)', async () => {
+      makeShellExecuteMock(() => {
+        throw new (class extends Error implements ProcessFailedError {
+          public readonly code = 'PROCESS_FAILED'
+          public readonly exitCode = 1
+          public readonly signal = null
+
+          constructor() {
+            super('foo');
+          }
+        });
+      });
+
+      const imageExists = await docker.exists('foo');
+
+      expect(imageExists).toBe(false);
+    });
+
+    test('returns false when the error is a shell failure and the exit code is 125 (Podman)', async () => {
+      makeShellExecuteMock(() => {
+        throw new (class extends Error implements ProcessFailedError {
+          public readonly code = 'PROCESS_FAILED'
+          public readonly exitCode = 125
+          public readonly signal = null
+
+          constructor() {
+            super('foo');
+          }
+        });
+      });
+
+      const imageExists = await docker.exists('foo');
+
+      expect(imageExists).toBe(false);
+    });
+  });
+});