diff --git a/lldb/source/Commands/CommandObjectTarget.cpp b/lldb/source/Commands/CommandObjectTarget.cpp
--- a/lldb/source/Commands/CommandObjectTarget.cpp
+++ b/lldb/source/Commands/CommandObjectTarget.cpp
@@ -299,12 +299,6 @@
 
       const char *file_path = command.GetArgumentAtIndex(0);
       LLDB_SCOPED_TIMERF("(lldb) target create '%s'", file_path);
-      FileSpec file_spec;
-
-      if (file_path) {
-        file_spec.SetFile(file_path, FileSpec::Style::native);
-        FileSystem::Instance().Resolve(file_spec);
-      }
 
       bool must_set_platform_path = false;
 
@@ -333,6 +327,18 @@
 
       PlatformSP platform_sp = target_sp->GetPlatform();
 
+      FileSpec file_spec;
+      if (file_path) {
+        file_spec.SetFile(file_path, FileSpec::Style::native);
+        FileSystem::Instance().Resolve(file_spec);
+
+        // Try to resolve the exe based on PATH and/or platform-specific
+        // suffixes, but only if using the host platform.
+        if (platform_sp && platform_sp->IsHost() &&
+            !FileSystem::Instance().Exists(file_spec))
+          FileSystem::Instance().ResolveExecutableLocation(file_spec);
+      }
+
       if (remote_file) {
         if (platform_sp) {
           // I have a remote file.. two possible cases
diff --git a/lldb/source/Target/TargetList.cpp b/lldb/source/Target/TargetList.cpp
--- a/lldb/source/Target/TargetList.cpp
+++ b/lldb/source/Target/TargetList.cpp
@@ -121,6 +121,14 @@
   if (!user_exe_path.empty()) {
     ModuleSpec module_spec(FileSpec(user_exe_path, FileSpec::Style::native));
     FileSystem::Instance().Resolve(module_spec.GetFileSpec());
+
+    // Try to resolve the exe based on PATH and/or platform-specific suffixes,
+    // but only if using the host platform.
+    if (platform_sp->IsHost() &&
+        !FileSystem::Instance().Exists(module_spec.GetFileSpec()))
+      FileSystem::Instance().ResolveExecutableLocation(
+          module_spec.GetFileSpec());
+
     // Resolve the executable in case we are given a path to a application
     // bundle like a .app bundle on MacOSX.
     Host::ResolveExecutableInBundle(module_spec.GetFileSpec());
diff --git a/lldb/test/Shell/Commands/command-target-create-resolve-exe.test b/lldb/test/Shell/Commands/command-target-create-resolve-exe.test
new file mode 100644
--- /dev/null
+++ b/lldb/test/Shell/Commands/command-target-create-resolve-exe.test
@@ -0,0 +1,28 @@
+# REQUIRES: system-windows
+
+## This checks that when starting lldb (or using `target create`) with a
+## program name which is on $PATH, or not specify the .exe suffix of a program
+## in the working directory on Windows, lldb can still detect the target
+## architecture correctly instead of producing an error.
+
+# RUN: mkdir -p "%t.dir"
+# RUN: %clang_host -g0 -O0 %S/Inputs/main.c -o %t.dir/testmain.exe
+
+## Test with full path to exe
+# RUN: %lldb %t.dir/testmain.exe -b | FileCheck %s
+
+## Test with exe on path, with .exe suffix
+# RUN: env "PATH=%t.dir;%PATH%" %lldb testmain.exe -b | FileCheck %s
+
+## Test with exe on path, without .exe suffix
+# RUN: env "PATH=%t.dir;%PATH%" %lldb testmain -b | FileCheck %s
+
+## Test in cwd, with .exe suffix
+# RUN: cd "%t.dir" && %lldb testmain.exe -b | FileCheck %s
+
+## Test in cwd, without .exe suffix
+# RUN: cd "%t.dir" && %lldb testmain -b | FileCheck %s
+
+# CHECK-LABEL: target create
+# CHECK-NEXT: Current executable set to '{{.*[/\\]}}testmain.exe'
+# CHECK-NOT: Error