diff --git a/CONTRIBUTING.md b/CONTRIBUTING.md
index c0e946609f9..311aebf7e65 100644
--- a/CONTRIBUTING.md
+++ b/CONTRIBUTING.md
@@ -345,14 +345,16 @@ The `aws.dev.forceDevMode` setting enables or disables Toolkit "dev mode". Witho
     -   Example: `getLogger().error('topic: widget failed: %O', { foo: 'bar', baz: 42 })`
 -   Log messages are written to the extension Output channel, which you can view in vscode by visiting the "Output" panel and selecting `AWS Toolkit Logs` or `Amazon Q Logs`.
 -   Use the `aws.dev.logfile` setting to set the logfile path to a fixed location, so you can follow
-    and filter logs using shell tools like `tail` and `grep`. For example in settings.json,
-    ```
-    "aws.dev.logfile": "~/awstoolkit.log",
-    ```
-    then you can tail the logfile in your terminal:
-    ```
-    tail -F ~/awstoolkit.log
-    ```
+    and filter logs using shell tools like `tail` and `grep`.
+    -   Note: this always logs at **debug log-level** (though you can temporarily override that from the `AWS Toolkit Logs` UI).
+    -   Example `settings.json`:
+        ```
+        "aws.dev.logfile": "~/awstoolkit.log",
+        ```
+        then you can tail the logfile in your terminal:
+        ```
+        tail -F ~/awstoolkit.log
+        ```
 -   Use the `AWS (Developer): Watch Logs` command to watch and filter Toolkit logs (including
     telemetry) in VSCode.
     -   Only available if you enabled "dev mode" (`aws.dev.forceDevMode` setting, see above).
diff --git a/packages/core/src/shared/logger/activation.ts b/packages/core/src/shared/logger/activation.ts
index a7c12e95513..29d8f8f6fd9 100644
--- a/packages/core/src/shared/logger/activation.ts
+++ b/packages/core/src/shared/logger/activation.ts
@@ -35,7 +35,7 @@ export async function activate(
 
     const mainLogger = makeLogger({
         logLevel: chanLogLevel,
-        logPaths: logUri ? [logUri] : undefined,
+        logFile: logUri,
         outputChannels: [logChannel],
         useConsoleLog: isWeb(),
     })
@@ -43,6 +43,7 @@ export async function activate(
         const newLogLevel = fromVscodeLogLevel(logLevel)
         mainLogger.setLogLevel(newLogLevel) // Also logs a message.
     })
+    mainLogger.setLogLevel('debug') // HACK: set to "debug" when debugging the extension.
 
     setLogger(mainLogger)
 
@@ -56,7 +57,7 @@ export async function activate(
         'debugConsole'
     )
 
-    getLogger().info('Log level: %s%s', chanLogLevel, logUri ? `, file: ${logUri.fsPath}` : '')
+    getLogger().info('Log level: %s%s', chanLogLevel, logUri ? `, file (always "debug" level): ${logUri.fsPath}` : '')
     getLogger().debug('User agent: %s', getUserAgent({ includePlatform: true, includeClientId: true }))
     if (devLogfile && typeof devLogfile !== 'string') {
         getLogger().error('invalid aws.dev.logfile setting')
@@ -69,20 +70,23 @@ export async function activate(
 /**
  * Creates a logger off of specified params
  * @param opts.logLevel Log messages at or above this level
- * @param opts.logPaths Array of paths to output log entries to
+ * @param opts.logFile See {@link Logger.logFile}
  * @param opts.outputChannels Array of output channels to log entries to
  * @param opts.useConsoleLog If true, outputs log entries to the nodejs or browser devtools console.
  */
 export function makeLogger(opts: {
     logLevel: LogLevel
-    logPaths?: vscode.Uri[]
+    logFile?: vscode.Uri
     outputChannels?: vscode.OutputChannel[]
     useConsoleLog?: boolean
 }): Logger {
     const logger = new ToolkitLogger(opts.logLevel)
-    // debug console can show ANSI colors, output channels can not
-    for (const logPath of opts.logPaths ?? []) {
-        logger.logToFile(logPath)
+    if (opts.logFile) {
+        logger.logToFile(opts.logFile)
+        logger.logFile = opts.logFile
+        // XXX: `vscode.LogOutputChannel` does not support programmatically setting the log-level,
+        // so this has no effect there. But this at least enables sinking to `SharedFileTransport`.
+        logger.setLogLevel('debug')
     }
     for (const outputChannel of opts.outputChannels ?? []) {
         logger.logToOutputChannel(outputChannel)
diff --git a/packages/core/src/shared/logger/logger.ts b/packages/core/src/shared/logger/logger.ts
index a1a2dd6a225..3c602c2db35 100644
--- a/packages/core/src/shared/logger/logger.ts
+++ b/packages/core/src/shared/logger/logger.ts
@@ -12,6 +12,11 @@ const toolkitLoggers: {
 } = { main: undefined, debugConsole: undefined }
 
 export interface Logger {
+    /**
+     * Developer-only: Optional log file, which gets all log messages (regardless of the configured
+     * log-level).
+     */
+    logFile?: vscode.Uri
     debug(message: string | Error, ...meta: any[]): number
     verbose(message: string | Error, ...meta: any[]): number
     info(message: string | Error, ...meta: any[]): number
@@ -27,6 +32,8 @@ export interface Logger {
 }
 
 export abstract class BaseLogger implements Logger {
+    logFile?: vscode.Uri
+
     debug(message: string | Error, ...meta: any[]): number {
         return this.sendToLog('debug', message, ...meta)
     }
diff --git a/packages/core/src/test/shared/logger/activation.test.ts b/packages/core/src/test/shared/logger/activation.test.ts
index df78041ca83..a9167c70ee9 100644
--- a/packages/core/src/test/shared/logger/activation.test.ts
+++ b/packages/core/src/test/shared/logger/activation.test.ts
@@ -18,7 +18,7 @@ describe('makeLogger', function () {
     before(async function () {
         tempFolder = await makeTemporaryToolkitFolder()
         const logPath = vscode.Uri.joinPath(vscode.Uri.file(tempFolder), 'log.txt')
-        testLogger = makeLogger({ logLevel: 'debug', logPaths: [logPath] })
+        testLogger = makeLogger({ logLevel: 'debug', logFile: logPath })
     })
 
     after(async function () {