diff --git a/Sources/Services/ContainerAPIService/Client/Parser.swift b/Sources/Services/ContainerAPIService/Client/Parser.swift
index 74319cd7..753f9818 100644
--- a/Sources/Services/ContainerAPIService/Client/Parser.swift
+++ b/Sources/Services/ContainerAPIService/Client/Parser.swift
@@ -251,16 +251,25 @@ public struct Parser {
             var hasEntrypointOverride: Bool = false
             // ensure the entrypoint is honored if it has been explicitly set by the user
             if let entrypoint = managementFlags.entrypoint, !entrypoint.isEmpty {
-                result = [entrypoint]
+                result = [resolveExecutablePath(entrypoint, workingDir: workingDir)]
                 hasEntrypointOverride = true
             } else if let entrypoint = config?.entrypoint, !entrypoint.isEmpty {
-                result = entrypoint
+                var resolved = entrypoint
+                if let first = entrypoint.first {
+                    resolved[0] = resolveExecutablePath(first, workingDir: workingDir)
+                }
+                result = resolved
             }
+
             if !arguments.isEmpty {
                 result.append(contentsOf: arguments)
             } else {
                 if let cmd = config?.cmd, !hasEntrypointOverride, !cmd.isEmpty {
-                    result.append(contentsOf: cmd)
+                    var resolved = cmd
+                    if let first = cmd.first {
+                        resolved[0] = resolveExecutablePath(first, workingDir: workingDir)
+                    }
+                    result.append(contentsOf: resolved)
                 }
             }
             return result.count > 0 ? result : nil
@@ -877,4 +886,21 @@ public struct Parser {
         default: return nil
         }
     }
+
+    // MARK: Private
+
+    private static func resolveExecutablePath(_ path: String, workingDir: String) -> String {
+        if path.hasPrefix("/") {
+            return path
+        }
+
+        if path.hasPrefix("./") || path.hasPrefix("../") {
+            return URL(fileURLWithPath: workingDir)
+                .appendingPathComponent(path)
+                .standardized
+                .path
+        }
+
+        return path
+    }
 }
diff --git a/Tests/ContainerAPIClientTests/ParserTest.swift b/Tests/ContainerAPIClientTests/ParserTest.swift
index b88b4c5a..6b70c339 100644
--- a/Tests/ContainerAPIClientTests/ParserTest.swift
+++ b/Tests/ContainerAPIClientTests/ParserTest.swift
@@ -14,8 +14,10 @@
 // limitations under the License.
 //===----------------------------------------------------------------------===//
 
+import ArgumentParser
 import ContainerizationError
 import ContainerizationExtras
+import ContainerizationOCI
 import Foundation
 import Testing
 
@@ -845,4 +847,150 @@ struct ParserTest {
             return error.description.contains("invalid property format")
         }
     }
+
+    @Test
+    func testProcessEntrypointRelativePathWithDotSlash() throws {
+        let processFlags = try Flags.Process.parse(["--cwd", "/usr/local/cargo/bin"])
+        let managementFlags = try Flags.Management.parse(["--entrypoint", "./rustc"])
+
+        let result = try Parser.process(
+            arguments: ["--version"],
+            processFlags: processFlags,
+            managementFlags: managementFlags,
+            config: nil
+        )
+
+        #expect(result.executable == "/usr/local/cargo/bin/rustc")
+        #expect(result.arguments == ["--version"])
+        #expect(result.workingDirectory == "/usr/local/cargo/bin")
+    }
+
+    @Test
+    func testProcessEntrypointBareCommand() throws {
+        let processFlags = try Flags.Process.parse(["--cwd", "/usr/bin"])
+        let managementFlags = try Flags.Management.parse(["--entrypoint", "python3"])
+
+        let result = try Parser.process(
+            arguments: ["-c", "print('hello')"],
+            processFlags: processFlags,
+            managementFlags: managementFlags,
+            config: nil
+        )
+
+        #expect(result.executable == "python3")
+        #expect(result.arguments == ["-c", "print('hello')"])
+    }
+
+    @Test
+    func testProcessEntrypointBareCommandWithRootWorkdir() throws {
+        let processFlags = try Flags.Process.parse(["--cwd", "/"])
+        let managementFlags = try Flags.Management.parse(["--entrypoint", "ls"])
+
+        let result = try Parser.process(
+            arguments: ["-la"],
+            processFlags: processFlags,
+            managementFlags: managementFlags,
+            config: nil
+        )
+
+        #expect(result.executable == "ls")
+        #expect(result.arguments == ["-la"])
+    }
+
+    @Test
+    func testProcessEntrypointAbsolutePathUnchanged() throws {
+        let processFlags = try Flags.Process.parse(["--cwd", "/home/user"])
+        let managementFlags = try Flags.Management.parse(["--entrypoint", "/bin/bash"])
+
+        let result = try Parser.process(
+            arguments: ["-c", "echo hello"],
+            processFlags: processFlags,
+            managementFlags: managementFlags,
+            config: nil
+        )
+
+        #expect(result.executable == "/bin/bash")
+        #expect(result.arguments == ["-c", "echo hello"])
+    }
+
+    @Test
+    func testProcessEntrypointRelativePathNormalization() throws {
+        let processFlags = try Flags.Process.parse(["--cwd", "/usr/local/bin"])
+        let managementFlags = try Flags.Management.parse(["--entrypoint", "../lib/node"])
+
+        let result = try Parser.process(
+            arguments: ["--version"],
+            processFlags: processFlags,
+            managementFlags: managementFlags,
+            config: nil
+        )
+
+        #expect(result.executable == "/usr/local/lib/node")
+    }
+
+    @Test
+    func testProcessEntrypointRelativePathWithDefaultWorkdir() throws {
+        let processFlags = try Flags.Process.parse([])
+        let managementFlags = try Flags.Management.parse(["--entrypoint", "./app"])
+
+        let result = try Parser.process(
+            arguments: [],
+            processFlags: processFlags,
+            managementFlags: managementFlags,
+            config: nil
+        )
+
+        #expect(result.executable == "/app")
+    }
+
+    @Test
+    func testProcessEntrypointRelativePathWithComplexPath() throws {
+        let processFlags = try Flags.Process.parse(["--cwd", "/home/user/project"])
+        let managementFlags = try Flags.Management.parse(["--entrypoint", "./bin/../scripts/./run.sh"])
+
+        let result = try Parser.process(
+            arguments: [],
+            processFlags: processFlags,
+            managementFlags: managementFlags,
+            config: nil
+        )
+
+        #expect(result.executable == "/home/user/project/scripts/run.sh")
+    }
+
+    @Test
+    func testProcessRelativeEntrypointInImageConfig() throws {
+        let config = ContainerizationOCI.ImageConfig(
+            entrypoint: ["./start.sh"],
+            workingDir: "/app"
+        )
+
+        let result = try Parser.process(
+            arguments: [],
+            processFlags: try Flags.Process.parse([]),
+            managementFlags: try Flags.Management.parse([]),
+            config: config
+        )
+
+        #expect(result.executable == "/app/start.sh")
+    }
+
+    @Test
+    func testProcessRelativeCmdInImageConfig() throws {
+        let config = ContainerizationOCI.ImageConfig(
+            entrypoint: nil,
+            cmd: ["./run.py", "--fast"],
+            workingDir: "/scripts"
+        )
+
+        let result = try Parser.process(
+            arguments: [],
+            processFlags: try Flags.Process.parse([]),
+            managementFlags: try Flags.Management.parse([]),
+            config: config
+        )
+
+        #expect(result.executable == "/scripts/run.py")
+        #expect(result.arguments == ["--fast"])
+    }
 }