diff --git a/src/compiler/commandLineParser.ts b/src/compiler/commandLineParser.ts
index 2f8844897f906..7e65efb01b0a8 100644
--- a/src/compiler/commandLineParser.ts
+++ b/src/compiler/commandLineParser.ts
@@ -3120,7 +3120,10 @@ namespace ts {
             };
         }
         if (isImplicitGlob(spec)) {
-            return { key: spec, flags: WatchDirectoryFlags.Recursive };
+            return {
+                key: useCaseSensitiveFileNames ? spec : toFileNameLowerCase(spec),
+                flags: WatchDirectoryFlags.Recursive
+            };
         }
         return undefined;
     }
diff --git a/src/testRunner/unittests/tscWatch/programUpdates.ts b/src/testRunner/unittests/tscWatch/programUpdates.ts
index fb3e008c7d962..988be560f76a5 100644
--- a/src/testRunner/unittests/tscWatch/programUpdates.ts
+++ b/src/testRunner/unittests/tscWatch/programUpdates.ts
@@ -556,6 +556,30 @@ export class A {
             ]
         });
 
+        verifyTscWatch({
+            scenario,
+            subScenario: "can correctly update configured project when set of root files has changed through include",
+            commandLineArgs: ["-w", "-p", "."],
+            sys: () => {
+                const file1 = {
+                    path: `${projectRoot}/Project/file1.ts`,
+                    content: "export const x = 10;"
+                };
+                const configFile = {
+                    path: `${projectRoot}/Project/tsconfig.json`,
+                    content: JSON.stringify({ include: [".", "./**/*.json"] })
+                };
+                return createWatchedSystem([file1, libFile, configFile], { currentDirectory: `${projectRoot}/Project` });
+            },
+            changes: [
+                {
+                    caption: "Write file2",
+                    change: sys => sys.writeFile(`${projectRoot}/Project/file2.ts`, "export const y = 10;"),
+                    timeouts: checkSingleTimeoutQueueLengthAndRun
+                }
+            ]
+        });
+
         verifyTscWatch({
             scenario,
             subScenario: "can update configured project when set of root files was not changed",
diff --git a/tests/baselines/reference/tscWatch/programUpdates/can-correctly-update-configured-project-when-set-of-root-files-has-changed-through-include.js b/tests/baselines/reference/tscWatch/programUpdates/can-correctly-update-configured-project-when-set-of-root-files-has-changed-through-include.js
new file mode 100644
index 0000000000000..5c818908e09f5
--- /dev/null
+++ b/tests/baselines/reference/tscWatch/programUpdates/can-correctly-update-configured-project-when-set-of-root-files-has-changed-through-include.js
@@ -0,0 +1,124 @@
+Input::
+//// [/user/username/projects/myproject/Project/file1.ts]
+export const x = 10;
+
+//// [/a/lib/lib.d.ts]
+/// <reference no-default-lib="true"/>
+interface Boolean {}
+interface Function {}
+interface CallableFunction {}
+interface NewableFunction {}
+interface IArguments {}
+interface Number { toExponential: any; }
+interface Object {}
+interface RegExp {}
+interface String { charAt: any; }
+interface Array<T> { length: number; [n: number]: T; }
+
+//// [/user/username/projects/myproject/Project/tsconfig.json]
+{"include":[".","./**/*.json"]}
+
+
+/a/lib/tsc.js -w -p .
+Output::
+>> Screen clear
+[12:00:23 AM] Starting compilation in watch mode...
+
+
+[12:00:26 AM] Found 0 errors. Watching for file changes.
+
+
+
+Program root files: ["/user/username/projects/myproject/Project/file1.ts"]
+Program options: {"watch":true,"project":"/user/username/projects/myproject/Project","configFilePath":"/user/username/projects/myproject/Project/tsconfig.json"}
+Program files::
+/a/lib/lib.d.ts
+/user/username/projects/myproject/Project/file1.ts
+
+Semantic diagnostics in builder refreshed for::
+/a/lib/lib.d.ts
+/user/username/projects/myproject/Project/file1.ts
+
+WatchedFiles::
+/user/username/projects/myproject/project/tsconfig.json:
+  {"fileName":"/user/username/projects/myproject/Project/tsconfig.json","pollingInterval":250}
+/user/username/projects/myproject/project/file1.ts:
+  {"fileName":"/user/username/projects/myproject/Project/file1.ts","pollingInterval":250}
+/a/lib/lib.d.ts:
+  {"fileName":"/a/lib/lib.d.ts","pollingInterval":250}
+
+FsWatches::
+
+FsWatchesRecursive::
+/user/username/projects/myproject/project/node_modules/@types:
+  {"directoryName":"/user/username/projects/myproject/Project/node_modules/@types","fallbackPollingInterval":500,"fallbackOptions":{"watchFile":"PriorityPollingInterval"}}
+/user/username/projects/myproject/node_modules/@types:
+  {"directoryName":"/user/username/projects/myproject/node_modules/@types","fallbackPollingInterval":500,"fallbackOptions":{"watchFile":"PriorityPollingInterval"}}
+/user/username/projects/myproject/project:
+  {"directoryName":"/user/username/projects/myproject/project","fallbackPollingInterval":500,"fallbackOptions":{"watchFile":"PriorityPollingInterval"}}
+
+exitCode:: ExitStatus.undefined
+
+//// [/user/username/projects/myproject/Project/file1.js]
+"use strict";
+exports.__esModule = true;
+exports.x = void 0;
+exports.x = 10;
+
+
+
+Change:: Write file2
+
+Input::
+//// [/user/username/projects/myproject/Project/file2.ts]
+export const y = 10;
+
+
+Output::
+>> Screen clear
+[12:00:29 AM] File change detected. Starting incremental compilation...
+
+
+[12:00:32 AM] Found 0 errors. Watching for file changes.
+
+
+
+Program root files: ["/user/username/projects/myproject/Project/file1.ts","/user/username/projects/myproject/Project/file2.ts"]
+Program options: {"watch":true,"project":"/user/username/projects/myproject/Project","configFilePath":"/user/username/projects/myproject/Project/tsconfig.json"}
+Program files::
+/a/lib/lib.d.ts
+/user/username/projects/myproject/Project/file1.ts
+/user/username/projects/myproject/Project/file2.ts
+
+Semantic diagnostics in builder refreshed for::
+/user/username/projects/myproject/Project/file2.ts
+
+WatchedFiles::
+/user/username/projects/myproject/project/tsconfig.json:
+  {"fileName":"/user/username/projects/myproject/Project/tsconfig.json","pollingInterval":250}
+/user/username/projects/myproject/project/file1.ts:
+  {"fileName":"/user/username/projects/myproject/Project/file1.ts","pollingInterval":250}
+/a/lib/lib.d.ts:
+  {"fileName":"/a/lib/lib.d.ts","pollingInterval":250}
+/user/username/projects/myproject/project/file2.ts:
+  {"fileName":"/user/username/projects/myproject/Project/file2.ts","pollingInterval":250}
+
+FsWatches::
+
+FsWatchesRecursive::
+/user/username/projects/myproject/project/node_modules/@types:
+  {"directoryName":"/user/username/projects/myproject/Project/node_modules/@types","fallbackPollingInterval":500,"fallbackOptions":{"watchFile":"PriorityPollingInterval"}}
+/user/username/projects/myproject/node_modules/@types:
+  {"directoryName":"/user/username/projects/myproject/node_modules/@types","fallbackPollingInterval":500,"fallbackOptions":{"watchFile":"PriorityPollingInterval"}}
+/user/username/projects/myproject/project:
+  {"directoryName":"/user/username/projects/myproject/project","fallbackPollingInterval":500,"fallbackOptions":{"watchFile":"PriorityPollingInterval"}}
+
+exitCode:: ExitStatus.undefined
+
+//// [/user/username/projects/myproject/Project/file2.js]
+"use strict";
+exports.__esModule = true;
+exports.y = void 0;
+exports.y = 10;
+
+