diff --git a/docs/OPERATIONS.md b/docs/OPERATIONS.md
index 58642e7b9..652cbaf19 100644
--- a/docs/OPERATIONS.md
+++ b/docs/OPERATIONS.md
@@ -85,6 +85,26 @@ Alerts are sent to PagerDuty and Slack (#ops-alerts channel).
 | DBConnectionPool | Pool exhaustion risk | Critical | 10 minutes |
 | QueueBacklog | Queue depth > 10000 for 5 minutes | Warning | 15 minutes |
 
+### Frailbox Legacy Logger File Failures
+
+The C frailbox components still use the legacy logger in
+`frailbox/src/logger.c`. When `LOG_FILE` points to a path that cannot be
+opened, configured for line buffering, written, flushed, or closed, the logger
+prints a diagnostic message to `stderr` and continues logging to `stderr`
+instead of aborting the process.
+
+Operators can check whether the fallback path was used by calling
+`log_get_fallback_count()` from a test harness or diagnostic build. The
+repository includes a focused harness for the common failure modes:
+
+```bash
+cd frailbox
+make test-logger-errors
+```
+
+The harness verifies normal file logging, fallback when the configured log file
+cannot be opened, and fallback when writes fail after a file was opened.
+
 ## Incident Response
 
 ### Severity Levels
diff --git a/frailbox/Makefile b/frailbox/Makefile
index d4383d853..55b72120f 100644
--- a/frailbox/Makefile
+++ b/frailbox/Makefile
@@ -37,7 +37,14 @@ distclean: clean
 test: $(TARGET)
 	./$(TARGET) --sandbox-type seccomp --memory-limit 64 --verbose
 
+test-logger-errors: $(BUILDDIR)/tests/test_logger_errors
+	./$(BUILDDIR)/tests/test_logger_errors
+
+$(BUILDDIR)/tests/test_logger_errors: tests/test_logger_errors.c $(SRCDIR)/logger.c include/logger.h
+	@mkdir -p $(dir $@)
+	$(CC) $(CFLAGS) -I$(INCDIR) tests/test_logger_errors.c $(SRCDIR)/logger.c -o $@ $(LDFLAGS)
+
 valgrind: $(TARGET)
 	valgrind --leak-check=full --show-leak-kinds=all ./$(TARGET)
 
-.PHONY: all clean distclean test valgrind
+.PHONY: all clean distclean test test-logger-errors valgrind
diff --git a/frailbox/include/logger.h b/frailbox/include/logger.h
index b9e2248c5..e6ad19c6e 100644
--- a/frailbox/include/logger.h
+++ b/frailbox/include/logger.h
@@ -229,6 +229,15 @@ void log_set_level(int level);
  */
 int log_get_level(void);
 
+/**
+ * Get the number of times the legacy logger had to fall back to stderr.
+ * This is primarily useful for diagnostics and regression tests around
+ * file-open, write, flush, and close failures.
+ *
+ * @return Number of fallback events observed in this process
+ */
+unsigned int log_get_fallback_count(void);
+
 /**
  * Log a formatted message at the specified level.
  * This is the core logging function. All LOG_* macros call this.
diff --git a/frailbox/src/logger.c b/frailbox/src/logger.c
index f1a7aa1a3..92b3201d6 100644
--- a/frailbox/src/logger.c
+++ b/frailbox/src/logger.c
@@ -128,6 +128,8 @@ static int g_log_level = DEFAULT_LOG_LEVEL;
  * TODO: Add automatic log file reopening after SIGHUP.
  */
 static FILE *g_log_file = NULL;
+static int g_log_file_is_stderr = 1;
+static unsigned int g_log_fallback_count = 0;
 
 /**
  * Whether to include timestamps in log output.
@@ -177,6 +179,24 @@ static char g_module_name[64] = "frailbox";
  */
 static pid_t g_pid = 0;
 
+static void logger_fallback_to_stderr(const char *operation,
+                                      const char *path,
+                                      int errnum)
+{
+    const char *safe_operation = operation != NULL ? operation : "log file operation";
+    const char *safe_path = path != NULL ? path : "<configured log stream>";
+
+    fprintf(stderr, "Legacy logger: %s failed for '%s': %s; falling back to stderr\n",
+            safe_operation, safe_path, strerror(errnum));
+
+    if (g_log_file != NULL && g_log_file != stderr) {
+        fclose(g_log_file);
+    }
+    g_log_file = stderr;
+    g_log_file_is_stderr = 1;
+    g_log_fallback_count++;
+}
+
 /* ------------------------------------------------------------------ */
 /* INTERNAL HELPERS                                                    */
 /* ------------------------------------------------------------------ */
@@ -377,15 +397,18 @@ int log_init(void)
 
     const char *env_log_file = getenv("LOG_FILE");
     if (env_log_file != NULL && strlen(env_log_file) > 0) {
+        errno = 0;
         g_log_file = fopen(env_log_file, "a");
         if (g_log_file == NULL) {
-            fprintf(stderr, "Failed to open log file '%s': %s\n",
-                    env_log_file, strerror(errno));
-            /* Fall back to stderr */
-            g_log_file = stderr;
+            logger_fallback_to_stderr("open", env_log_file, errno);
+        } else if (setvbuf(g_log_file, NULL, _IOLBF, 0) != 0) {
+            logger_fallback_to_stderr("configure buffering", env_log_file, errno);
+        } else {
+            g_log_file_is_stderr = 0;
         }
     } else {
         g_log_file = stderr;
+        g_log_file_is_stderr = 1;
     }
 
     const char *env_module = getenv("LOG_MODULE");
@@ -445,6 +468,15 @@ int log_get_level(void)
     return level;
 }
 
+unsigned int log_get_fallback_count(void)
+{
+    unsigned int count;
+    pthread_mutex_lock(&log_mutex);
+    count = g_log_fallback_count;
+    pthread_mutex_unlock(&log_mutex);
+    return count;
+}
+
 /**
  * Core logging function. All log macros call this function.
  *
@@ -525,13 +557,18 @@ void log_message(int level, const char *file, int line, const char *fmt, ...)
         buffer[total_len + 1] = '\0';
     }
 
-    /* Write to output */
-    if (g_log_file != NULL) {
-        fputs(buffer, g_log_file);
-        fflush(g_log_file);
-    } else {
-        fputs(buffer, stderr);
-        fflush(stderr);
+    /* Write to output; fall back to stderr if the configured file fails. */
+    FILE *target = g_log_file != NULL ? g_log_file : stderr;
+    errno = 0;
+    if (fputs(buffer, target) == EOF || fflush(target) == EOF) {
+        int write_errno = errno != 0 ? errno : EIO;
+        if (!g_log_file_is_stderr) {
+            logger_fallback_to_stderr("write", getenv("LOG_FILE"), write_errno);
+            fputs(buffer, stderr);
+            fflush(stderr);
+        } else {
+            fprintf(stderr, "Legacy logger: stderr write failed: %s\n", strerror(write_errno));
+        }
     }
 
     pthread_mutex_unlock(&log_mutex);
@@ -551,10 +588,19 @@ void log_shutdown(void)
     pthread_mutex_lock(&log_mutex);
 
     if (g_log_file != NULL && g_log_file != stderr) {
-        fflush(g_log_file);
-        fclose(g_log_file);
+        if (fflush(g_log_file) == EOF) {
+            logger_fallback_to_stderr("flush during shutdown", getenv("LOG_FILE"), errno != 0 ? errno : EIO);
+        } else if (fclose(g_log_file) == EOF) {
+            fprintf(stderr, "Legacy logger: close during shutdown failed for '%s': %s; falling back to stderr\n",
+                    getenv("LOG_FILE") != NULL ? getenv("LOG_FILE") : "<configured log stream>",
+                    strerror(errno != 0 ? errno : EIO));
+            g_log_file = stderr;
+            g_log_file_is_stderr = 1;
+            g_log_fallback_count++;
+        }
         g_log_file = NULL;
     }
+    g_log_file_is_stderr = 1;
 
     g_log_level = LOG_LEVEL_NONE;
 
diff --git a/frailbox/tests/test_logger_errors.c b/frailbox/tests/test_logger_errors.c
new file mode 100644
index 000000000..3095e1eb8
--- /dev/null
+++ b/frailbox/tests/test_logger_errors.c
@@ -0,0 +1,58 @@
+#include <stdio.h>
+#include <stdlib.h>
+#include <string.h>
+#include <unistd.h>
+
+#include "../include/logger.h"
+
+static int expect_true(int condition, const char *message)
+{
+    if (!condition) {
+        fprintf(stderr, "FAIL: %s\n", message);
+        return 1;
+    }
+    return 0;
+}
+
+int main(void)
+{
+    int failures = 0;
+    char template_path[] = "/tmp/frailbox-logger-XXXXXX";
+    int fd = mkstemp(template_path);
+    if (fd < 0) {
+        perror("mkstemp");
+        return 1;
+    }
+    close(fd);
+
+    setenv("LOG_LEVEL", "info", 1);
+    setenv("LOG_FILE", template_path, 1);
+    failures += expect_true(log_init() == 0, "log_init succeeds for writable file");
+    LOG_INFO("normal file write");
+    failures += expect_true(log_get_fallback_count() == 0, "writable file does not trigger fallback");
+    log_shutdown();
+
+    setenv("LOG_LEVEL", "info", 1);
+    setenv("LOG_FILE", "/tmp/frailbox-missing-dir/logger.log", 1);
+    failures += expect_true(log_init() == 0, "log_init succeeds with stderr fallback");
+    failures += expect_true(log_get_fallback_count() >= 1, "open failure increments fallback count");
+    LOG_WARN("fallback after open failure");
+    log_shutdown();
+
+    setenv("LOG_LEVEL", "info", 1);
+    setenv("LOG_FILE", "/dev/full", 1);
+    unsigned int before = log_get_fallback_count();
+    failures += expect_true(log_init() == 0, "log_init succeeds for /dev/full");
+    LOG_ERROR("write should fall back from /dev/full");
+    failures += expect_true(log_get_fallback_count() > before, "write failure increments fallback count");
+    log_shutdown();
+
+    unlink(template_path);
+    unsetenv("LOG_FILE");
+    unsetenv("LOG_LEVEL");
+
+    if (failures == 0) {
+        printf("logger error handling tests passed\n");
+    }
+    return failures == 0 ? 0 : 1;
+}