diff --git a/R/relational-duckdb.R b/R/relational-duckdb.R
index fb857efe..5c18bb9d 100644
--- a/R/relational-duckdb.R
+++ b/R/relational-duckdb.R
@@ -27,8 +27,8 @@ duckplyr_macros <- c(
   "is.na" = "(x) AS (x IS NULL)",
   "n" = "() AS CAST(COUNT(*) AS int32)",
   #
-  "log10" = "(x) AS log(x)",
-  "log" = "(x) AS ln(x)",
+  "log10" = "(x) AS CASE WHEN x < 0 THEN CAST('NaN' AS double) WHEN x = 0 THEN CAST('-Inf' AS double) ELSE log(x) END",
+  "log" = "(x) AS CASE WHEN x < 0 THEN CAST('NaN' AS double) WHEN x = 0 THEN CAST('-Inf' AS double) ELSE ln(x) END",
   # TPCH
 
   # https://github.com/duckdb/duckdb/discussions/8599
diff --git a/tests/testthat/test-as_duckplyr_df.R b/tests/testthat/test-as_duckplyr_df.R
index 9379ed5b..68d285eb 100644
--- a/tests/testthat/test-as_duckplyr_df.R
+++ b/tests/testthat/test-as_duckplyr_df.R
@@ -1304,6 +1304,34 @@ test_that("as_duckplyr_df() and mutate(c = 0, d = 0, e = c / d)", {
   expect_equal(pre, post)
 })
 
+
+test_that("as_duckplyr_df() and mutate(c = 0, d = -1, e = log(c), f = log(d))", {
+  # Data
+  test_df <- data.frame(a = 1:6 + 0, b = 2, g = rep(1:3, 1:3))
+
+  # Run
+  pre <- test_df %>% as_duckplyr_df() %>% mutate(c = 0, d = -1, e = log(c), f = log(d))
+  # FIXME: This is overwritten by autogeneration but necessary, find better solution
+  post <- test_df %>% mutate(c = 0, d = -1, e = log(c), f = suppressWarnings(log(d))) %>% as_duckplyr_df()
+
+  # Compare
+  expect_equal(pre, post)
+})
+
+
+test_that("as_duckplyr_df() and mutate(c = 0, d = -1, e = log(c), f = log10(d))", {
+  # Data
+  test_df <- data.frame(a = 1:6 + 0, b = 2, g = rep(1:3, 1:3))
+
+  # Run
+  pre <- test_df %>% as_duckplyr_df() %>% mutate(c = 0, d = -1, e = log(c), f = log10(d))
+  # FIXME: This is overwritten by autogeneration but necessary, find better solution
+  post <- test_df %>% mutate(c = 0, d = -1, e = log(c), f = suppressWarnings(log10(d))) %>% as_duckplyr_df()
+
+  # Compare
+  expect_equal(pre, post)
+})
+
 test_that("as_duckplyr_df() and nest_by()", {
   withr::local_envvar(DUCKPLYR_FORCE = "FALSE")
 
diff --git a/tools/00-funs.R b/tools/00-funs.R
index 57104d15..1d138b38 100644
--- a/tools/00-funs.R
+++ b/tools/00-funs.R
@@ -601,6 +601,10 @@ test_extra_arg_map <- list(
     # Division by zero
     "c = 0, d = 0, e = c / d",
 
+    # Negative log
+    "c = 0, d = -1, e = log(c), f = log(d)",
+    "c = 0, d = -1, e = log(c), f = log10(d)",
+
     NULL
   ),
   nest_join = "join_by(a)",