diff --git a/DESCRIPTION b/DESCRIPTION
index 9e0e29d5d..d1e211bca 100644
--- a/DESCRIPTION
+++ b/DESCRIPTION
@@ -56,6 +56,7 @@ Collate:
     'commas_linter.R'
     'comment_linters.R'
     'comments.R'
+    'conjunct_expectation_linter.R'
     'cyclocomp_linter.R'
     'declared_functions.R'
     'deprecated.R'
diff --git a/NAMESPACE b/NAMESPACE
index 057bf62d7..2192f7c64 100644
--- a/NAMESPACE
+++ b/NAMESPACE
@@ -21,6 +21,7 @@ export(clear_cache)
 export(closed_curly_linter)
 export(commas_linter)
 export(commented_code_linter)
+export(conjunct_expectation_linter)
 export(cyclocomp_linter)
 export(default_linters)
 export(default_settings)
diff --git a/NEWS.md b/NEWS.md
index ae8694fa0..04d680fcb 100644
--- a/NEWS.md
+++ b/NEWS.md
@@ -90,6 +90,7 @@ function calls. (#850, #851, @renkun-ken)
    + `expect_type_linter()` Require usage of `expect_type(x, t)` over `expect_equal(typeof(x), t)` and similar
    + `expect_s3_class_linter()` Require usage of `expect_s3_class(x, k)` over `expect_equal(class(x), k)` and similar
    + `expect_s4_class_linter()` Require usage of `expect_s4_class(x, k)` over `expect_true(methods::is(x, k))`
+   + `conjunct_expectation_linter()` Require usage of `expect_true(x); expect_true(y)` over `expect_true(x && y)` and similar
    + `expect_not_linter()` Require usage of `expect_false(x)` over `expect_true(!x)`, and _vice versa_.
    + `expect_true_false_linter()` Require usage of `expect_true(x)` over `expect_equal(x, TRUE)` and similar
    + `expect_named_linter()` Require usage of `expect_named(x, n)` over `expect_equal(names(x), n)` and similar
diff --git a/R/conjunct_expectation_linter.R b/R/conjunct_expectation_linter.R
new file mode 100644
index 000000000..222ea8dcd
--- /dev/null
+++ b/R/conjunct_expectation_linter.R
@@ -0,0 +1,47 @@
+#' Force && conditions in expect_true(), expect_false() to be written separately
+#'
+#' For readability of test outputs, testing only one thing per call to
+#'   [testthat::expect_true()] is preferable, i.e.,
+#'   `expect_true(A); expect_true(B)` is better than `expect_true(A && B)`, and
+#'   `expect_false(A); expect_false(B)` is better than `expect_false(A || B)`.
+#'
+#' @evalRd rd_tags("expect_true_false_and_condition_linter")
+#' @seealso [linters] for a complete list of linters available in lintr.
+#' @export
+conjunct_expectation_linter <- function() {
+  Linter(function(source_file) {
+    # need the full file to also catch usages at the top level
+    if (length(source_file$full_parsed_content) == 0L) {
+      return(list())
+    }
+
+    xml <- source_file$full_xml_parsed_content
+
+    xpath <- "//expr[
+      (
+        expr[SYMBOL_FUNCTION_CALL[text() = 'expect_true']]
+        and expr[2][AND2]
+      ) or (
+        expr[SYMBOL_FUNCTION_CALL[text() = 'expect_false']]
+        and expr[2][OR2]
+      )
+    ]"
+
+    bad_expr <- xml2::xml_find_all(xml, xpath)
+
+    return(lapply(
+      bad_expr,
+      xml_nodes_to_lint,
+      source_file,
+      lint_message = function(expr) {
+        matched_fun <- xml2::xml_text(xml2::xml_find_first(expr, "expr/SYMBOL_FUNCTION_CALL"))
+        op <- if (matched_fun == "expect_true") "&&" else "||"
+        message <-
+          sprintf("Instead of %1$s(A %2$s B), write multiple expectations like %1$s(A) and %1$s(B)", matched_fun, op)
+        paste(message, "The latter will produce better error messages in the case of failure.")
+      },
+      type = "warning",
+      global = TRUE
+    ))
+  })
+}
diff --git a/inst/lintr/linters.csv b/inst/lintr/linters.csv
index 6bc68ebff..0600e6795 100644
--- a/inst/lintr/linters.csv
+++ b/inst/lintr/linters.csv
@@ -5,6 +5,7 @@ backport_linter,robustness configurable package_development
 closed_curly_linter,style readability default configurable
 commas_linter,style readability default
 commented_code_linter,style readability best_practices default
+conjunct_expectation_linter,package_development best_practices readability
 cyclocomp_linter,style readability best_practices default configurable
 duplicate_argument_linter,correctness common_mistakes configurable
 equals_na_linter,robustness correctness common_mistakes default
diff --git a/man/best_practices_linters.Rd b/man/best_practices_linters.Rd
index cd9fd1e32..91b21d619 100644
--- a/man/best_practices_linters.Rd
+++ b/man/best_practices_linters.Rd
@@ -14,6 +14,7 @@ The following linters are tagged with 'best_practices':
 \itemize{
 \item{\code{\link{absolute_path_linter}}}
 \item{\code{\link{commented_code_linter}}}
+\item{\code{\link{conjunct_expectation_linter}}}
 \item{\code{\link{cyclocomp_linter}}}
 \item{\code{\link{expect_comparison_linter}}}
 \item{\code{\link{expect_length_linter}}}
diff --git a/man/conjunct_expectation_linter.Rd b/man/conjunct_expectation_linter.Rd
new file mode 100644
index 000000000..1125e999e
--- /dev/null
+++ b/man/conjunct_expectation_linter.Rd
@@ -0,0 +1,20 @@
+% Generated by roxygen2: do not edit by hand
+% Please edit documentation in R/conjunct_expectation_linter.R
+\name{conjunct_expectation_linter}
+\alias{conjunct_expectation_linter}
+\title{Force && conditions in expect_true(), expect_false() to be written separately}
+\usage{
+conjunct_expectation_linter()
+}
+\description{
+For readability of test outputs, testing only one thing per call to
+\code{\link[testthat:logical-expectations]{testthat::expect_true()}} is preferable, i.e.,
+\verb{expect_true(A); expect_true(B)} is better than \code{expect_true(A && B)}, and
+\verb{expect_false(A); expect_false(B)} is better than \code{expect_false(A || B)}.
+}
+\seealso{
+\link{linters} for a complete list of linters available in lintr.
+}
+\section{Tags}{
+No tags are given.
+}
diff --git a/man/linters.Rd b/man/linters.Rd
index 801a480e6..843f5b04f 100644
--- a/man/linters.Rd
+++ b/man/linters.Rd
@@ -17,15 +17,15 @@ Documentation for linters is structured into tags to allow for easier discovery.
 \section{Tags}{
 The following tags exist:
 \itemize{
-\item{\link[=best_practices_linters]{best_practices} (19 linters)}
+\item{\link[=best_practices_linters]{best_practices} (20 linters)}
 \item{\link[=common_mistakes_linters]{common_mistakes} (5 linters)}
 \item{\link[=configurable_linters]{configurable} (16 linters)}
 \item{\link[=consistency_linters]{consistency} (7 linters)}
 \item{\link[=correctness_linters]{correctness} (7 linters)}
 \item{\link[=default_linters]{default} (25 linters)}
 \item{\link[=efficiency_linters]{efficiency} (4 linters)}
-\item{\link[=package_development_linters]{package_development} (12 linters)}
-\item{\link[=readability_linters]{readability} (24 linters)}
+\item{\link[=package_development_linters]{package_development} (13 linters)}
+\item{\link[=readability_linters]{readability} (25 linters)}
 \item{\link[=robustness_linters]{robustness} (10 linters)}
 \item{\link[=style_linters]{style} (31 linters)}
 }
@@ -39,6 +39,7 @@ The following linters exist:
 \item{\code{\link{closed_curly_linter}} (tags: configurable, default, readability, style)}
 \item{\code{\link{commas_linter}} (tags: default, readability, style)}
 \item{\code{\link{commented_code_linter}} (tags: best_practices, default, readability, style)}
+\item{\code{\link{conjunct_expectation_linter}} (tags: best_practices, package_development, readability)}
 \item{\code{\link{cyclocomp_linter}} (tags: best_practices, configurable, default, readability, style)}
 \item{\code{\link{duplicate_argument_linter}} (tags: common_mistakes, configurable, correctness)}
 \item{\code{\link{equals_na_linter}} (tags: common_mistakes, correctness, default, robustness)}
diff --git a/man/package_development_linters.Rd b/man/package_development_linters.Rd
index bbdb17f3f..9a9ff41e2 100644
--- a/man/package_development_linters.Rd
+++ b/man/package_development_linters.Rd
@@ -13,6 +13,7 @@ Linters useful to package developers, for example for writing consistent tests.
 The following linters are tagged with 'package_development':
 \itemize{
 \item{\code{\link{backport_linter}}}
+\item{\code{\link{conjunct_expectation_linter}}}
 \item{\code{\link{expect_comparison_linter}}}
 \item{\code{\link{expect_identical_linter}}}
 \item{\code{\link{expect_length_linter}}}
diff --git a/man/readability_linters.Rd b/man/readability_linters.Rd
index 2236178af..a8beec5f2 100644
--- a/man/readability_linters.Rd
+++ b/man/readability_linters.Rd
@@ -15,6 +15,7 @@ The following linters are tagged with 'readability':
 \item{\code{\link{closed_curly_linter}}}
 \item{\code{\link{commas_linter}}}
 \item{\code{\link{commented_code_linter}}}
+\item{\code{\link{conjunct_expectation_linter}}}
 \item{\code{\link{cyclocomp_linter}}}
 \item{\code{\link{expect_length_linter}}}
 \item{\code{\link{expect_named_linter}}}
diff --git a/tests/testthat/test-conjunct_expectation_linter.R b/tests/testthat/test-conjunct_expectation_linter.R
new file mode 100644
index 000000000..e14cc4bec
--- /dev/null
+++ b/tests/testthat/test-conjunct_expectation_linter.R
@@ -0,0 +1,59 @@
+test_that("conjunct_expectation_linter skips allowed usages of expect_true", {
+  expect_lint("expect_true(x)", NULL, conjunct_expectation_linter())
+  expect_lint("testthat::expect_true(x, y, z)", NULL, conjunct_expectation_linter())
+
+  # more complicated expression
+  expect_lint("expect_true(x || (y && z))", NULL, conjunct_expectation_linter())
+  # the same by operator precedence, though not obvious a priori
+  expect_lint("expect_true(x || y && z)", NULL, conjunct_expectation_linter())
+  expect_lint("expect_true(x && y || z)", NULL, conjunct_expectation_linter())
+})
+
+test_that("conjunct_expectation_linter skips allowed usages of expect_true", {
+  expect_lint("expect_false(x)", NULL, conjunct_expectation_linter())
+  expect_lint("testthat::expect_false(x, y, z)", NULL, conjunct_expectation_linter())
+
+  # more complicated expression
+  # (NB: xx && yy || zz and xx || yy && zz both parse with || first)
+  expect_lint("expect_false(x && (y || z))", NULL, conjunct_expectation_linter())
+})
+
+test_that("conjunct_expectation_linter blocks && conditions with expect_true()", {
+  expect_lint(
+    "expect_true(x && y)",
+    rex::rex("Instead of expect_true(A && B), write multiple expectations"),
+    conjunct_expectation_linter()
+  )
+
+  expect_lint(
+    "expect_true(x && y && z)",
+    rex::rex("Instead of expect_true(A && B), write multiple expectations"),
+    conjunct_expectation_linter()
+  )
+})
+
+test_that("conjunct_expectation_linter blocks || conditions with expect_false()", {
+  expect_lint(
+    "expect_false(x || y)",
+    rex::rex("Instead of expect_false(A || B), write multiple expectations"),
+    conjunct_expectation_linter()
+  )
+
+  expect_lint(
+    "expect_false(x || y || z)",
+    rex::rex("Instead of expect_false(A || B), write multiple expectations"),
+    conjunct_expectation_linter()
+  )
+
+  # these lint because `||` is always outer by operator precedence
+  expect_lint(
+    "expect_false(x || y && z)",
+    rex::rex("Instead of expect_false(A || B), write multiple expectations"),
+    conjunct_expectation_linter()
+  )
+  expect_lint(
+    "expect_false(x && y || z)",
+    rex::rex("Instead of expect_false(A || B), write multiple expectations"),
+    conjunct_expectation_linter()
+  )
+})